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For God and Liberty

Chapter Text

He looked at the cross in curiosity. The man was bound to it, looking to be in pain but also accepting of it. Guybrush looked at Elaine asking her what or rather– WHO this was and why was the bounded man sent to him.

She couldn’t answer him the why, but she did inform him he was Dismas, the penitent thief.


“He’s… never mind. It’s fine.”

They sailed off to Scotland, the bounded man had a map that guided them to their next destination so it was out with the warmth of the Caribbean sun and into the chiller region. And of course it was a slip of the hand that sent the cross tumbling down to reveal it’s hidden content. But what could this map be leading them to? Guybrush kept wondering until they reached the supposed graveyard.

Another map blanketed the floor at the end of the cavern of trials. How they managed to make it this far without dying (or at least, having a near-death experience) was a mystery to them, but they counted it as Lady Luck looking down upon them.

“Madagascar… a-a-and the star, that’s King’s Bay.” Guybrush pointed, feeling rather proud of himself at knowing his geography outside the Tri-Island area. Elaine supposed all those years out at sea, he was bound to memorize the world’s map.

Henry Avery was not amused.

The older pirate stood there tall and arms crossed, a scowl on his face and a look that could read disbelief and anger.  “Ye can’t be Threepwood.” He scoffed. “He’s older… stronger. You’re young and inexperienced. Stop with these poor excuse of a game and fetch your master, boy.”

“How can I not– what do I need to prove to you I am who I say I am?!”

There was a cruel chuckle as Henry drew out his sword and pointed it menacingly at Guybrush’s direction. The blond gulped but held his place, a sense of doubt creeping up about reconsidering having Elaine stay behind.

“They say he’s a fearsome pirate that can cut you down by both wit and sword. If you are, in fact, stating the truth… prove it.”

Guybrush, arms equally crossed, stared down the older man before he dug into his coat pocket and drew out the coin which glistened against the dim-lighted torch in the room, slamming it against the wooden table before pushing his coat away and allowing the hilt of his cutlass to shine.

“Where do you want me to start?”

“Liber– what?” Elaine raised a brow. The meeting with Henry took forever and she couldn’t help but feel nervous, even contemplating every now and again to break into their meeting and see if he was safe. But she kept her promise and trusted Guybrush to handle things on his own.

And seeing Guybrush returned with a shine in his eyes and a smile on his face subsided her fear for the time being. He went on for hours explaining this ‘safe haven of a utopia for pirates everywhere’ and a place where people can be ‘free from anyone or anything oppressing them’.

But most of all… they could have a place they can call home when they don’t have one to go to.

Something about it sounded… wrong. And yet, Henry Avery, the most notorious of pirates right now picked her husband as someone to stand along side him and ten or so other Pirate Captains to help build this haven. Elaine could tell by the looks in those blue eyes, Guybrush believed with all his heart in this Libertalia.

Who was she to douse that dream?

As a former politician, Elaine was no stranger to long-winded and boring conferences. And yet, sitting among the other leaders discussing the building plans… Elaine felt nervous, on edge even. But she wouldn’t show those signs at all. Especially not after Guybrush had to practically beg the other Captains to let Elaine sit in on a few of their meetings. Anne Bonnie scoffed, mocked Elaine to her face by comparing her to that of a child bringing his mother to school. Elaine bit her tongue so as not to hurt any chances Guybrush would have with his fellow pirates but the blond quickly stood up and shut Bonnie down with a quick insult for disrespecting his wife.

She felt flattered that he was quick to stand up for her, but then again, that’s just in Guybrush’s nature to defend those who need it.

If it was one thing Guybrush hated doing, it was standing in one place for too long.

“How much longer?” Guybrush whined.

“Just a few more minutes, dear.” Elaine reassured.

“You said that ten minutes ago.”

“It’s an oil painting, these things take time.”

Guybrush sagged his shoulders briefly before the painter yelled at him to stand tall, causing the blond to jump and go back to his original position even though his eyes now looked more scared than confident. Elaine suppressed her chuckle. She looked at the painting where he stood tall and confident compared to the blond who looked about ready to book it that it felt like she was looking at a different person. She recalled how dumbfounded he sounded when Tew explained that he needed to get his portraits done.

Guybrush asked to make sure he heard that correctly in that it was portraitS as in plural and not just A portrait.

Tew merely chuckled and patted Guybrush on the back before walking away.

“Whoa…” Guybrush gasped.

He stood in front of himself. Well, more like a giant statue of himself. It looked so confident, tall… and proud. Elaine glanced from the statue and looked at Guybrush, feeling a sense of pride herself knowing just how far her husband came along since he washed up ashore on Melee Island all those years ago when her smile shifted to a frown.

He was crying.

“Guybrush… are you okay? What’s wrong?” Elaine asked, placing her hands on him. He merely shook his head.

“Nothing… nothing is wrong… it’s just… it’s a lot, y’know?” Guybrush gave her a sincere smile. “I… I never thought I’d live to see something like this… to actually make a difference. I… sorry.”

He wiped his eyes and gave a chuckle with a muttered ‘God, I look pathetic’ as some of the other Captains– Founders, walked by. Elaine sighed and rubbed his shoulder, pulling him a bit closer to her so she could properly wrap her arms around him.

“I’m proud of you, my Mighty Pirate™ husband.” Elaine kissed Guybrush on the cheek, the blond laughed.

Avery and Tew kept calling Guybrush every night regarding Libertalia and it’s puzzles. For months on end, Guybrush was kept on his toes and busy giving input and even helping some of the construction workers build the newly hidden town, or rather, the passageway to the town. Avery assigned Guybrush with the puzzles so that only those who were clever enough would find it.

He obliged… to an extent.

Guybrush made sure the puzzles were a challenge, obviously, but he also made sure that those who needed refuge would be able to attain it. It was tricky… but not impossible. Just needed to think a little bit outside the box and like, well, a pirate.

He may be a Founder, but he wasn’t about to be a dick about it either.

Months passed and Libertalia began to form with it’s buildings slowly but surely come into being, the people slowly flocking to the new found haven, and the Founders being more busy than ever establishing basic guidelines to follow. They were strict… but simple.

Guybrush strolled along the streets with Elaine one day when a couple of children ran by giggling. The redhead looked over at her husband who looked to be in disbelief that he saw children running along the streets of Libertalia.

She gave his hand a tight squeeze and a smile.

“Look at that, Guybrush. They have a home… you did that.”

“Yeah… I did, didn’t I?” Guybrush whispered, a warm smile gracing his face.

“Can I open my eyes now?”

“Juuuuuuuust a bit, Plunder Bunny.”

“Guybrush, really…”

“Okay… now!”

Elaine took off her blinds and blinked, adjusting her eyes to the light and looked at mansion that easily defeated the one back on Melee just by sheer size. She covered her mouth to suppress a gasp and whipped her head at Guybrush.

“G-Guybrush… what–”

“It’s our new home. Kinda bummed we’re not… IN Libertalia and it’s a bit too flashy for my taste, but Avery and the others figured it would be best if we as Founders lived here. And seeing as this is far too big for me, you and Winslow will get to live here too!”

She brushed her hand against the monkey sigil that Avery bestowed on Guybrush before looking over at the blond. He looked happy… but he didn’t sound it, at least not until he mentioned her and Winslow. Still, she wasn’t about to rain on his parade and hugged him.

He stayed longer and longer in those meetings. Hearing the once hopeful optimistic talk shift to a more… serious tone. If he was going to be completely honest, it was boring to Guybrush. Suppose it would make sense, anything that was stuck in one place bore him quickly.

Guybrush also missed having Elaine join him on the meeting, but the more populated Libertalia began to be, the more the other Founders denied Elaine access to join in which baffled him because wouldn’t they want someone who ran not one but THREE islands to give some advice? Instead, he didn’t argue with them… not with the way they all stared at him.

He doodled briefly on a piece of parchment as the Founders began yammering about some underground activity or something of the sort when he jumped at the sudden table being slammed and noticed several eyes staring at him angrily.

Guess he needed to pay attention.

Guybrush came back from the meeting so worn out that he practically bee-lined it to their bedroom, kicked off his boots, and collapsed face first into their bed. As a Founder, that was beyond childish and he should know better, but both Elaine and Guybrush knew that this was a habit he wasn’t planning on getting rid of anytime soon.

Elaine brushed back some of the strands of blond from the sleeping pirate’s face. She was happy with Winslow’s company during the long periods of time when the blond wasn’t around and she was proud of Guybrush as one of Libertalia’s Founders, sure… but she was selfishly happy when he was fast asleep next to her. Of course, Elaine couldn’t say that to his face.

Not when he looked so hopeful and happy. But if she was going to be honest with herself, she missed Guybrush.

She missed seeing the blond standing alongside their first mate surrounded by a pile of worn maps trying to decipher where they were going. She missed hearing him shouting about there being yet another leak in their ship and frantically looking for tar. She missed hearing him occasionally hum an obscure tune when he thought no one was around. She missed seeing him sitting either at his desk, in the bed, or even on a pile of crates jotting down in his journal. She missed his laugh when he hears or said a ridiculous joke. She missed those little notes he would place around the ship for only Elaine to fine that said small things like ‘I love you’. She missed feeling him put his arms around her waist and pulling her into a tight hug.

She missed her husband.

But she couldn’t say that to his face and instead supported him. Libertalia may have Founder Threepwood for most of their time, but at the end of the day Guybrush Threepwood was her’s.

Guybrush missed walking down the streets of Libertalia. It always felt like he was caught up in a meeting or something that he wasn’t really given any time to just see the town they built and was stuck in New Devon which wasn’t SUCH a terrible place… but it was quiet compared to the bumbling crowd and laughs that Libertalia provided.

He didn’t pay much attention until he bumped into another pirate, causing the both of them to fall on the floor with an ungraceful ‘umph’.

“Sorry about that!! I ah… had my head in the clouds.” Guybrush apologized as he rubbed the back of his neck.

“Watch where yer goin’, ye good fer nuthin’ sea urchin!!” The pirate shouted until he widen his eyes, recognizing the blue coat. “F-F-Founder Threepwood! I am… truly sorry fer how I spoke.”

Guybrush raised an eyebrow. Was the pirate scared of him?

“No no… it’s my fault I–”

But before he could finish apology, the pirate ran off in terror and the crowd around him began murmuring. Guybrush stood up and brushed the dirt off his coat, giving a sheepish smile before excusing himself.

Another meeting and more talk about money. Why was this a topic? He thought they were all going to pool their resources so that everyone would benefit out of it. And yet, here they were. Avery looking just angrily calm as ever while the other Founders were shouting about a potential underground rebellion. What was going on?

“Founder Threepwood, what do you have to say about this?” Condent barked.

“I um… maybe if we just, I dunno, talked with them?” Guybrush shrugged.

“Again with that option…” Bonnie sighed in frustrations as she rubbed the bridged of her nose.

“Yes. Again with that option!” Guybrush countered.

“That’s ALL you have for an option!”

“No– well, yeah. But listen! If we just talked to the colonists about what was going I’m sure–”

“Enough.” Avery commanded with a booming voice, causing the other Founders to fall silent. “We have no need to talk with them, we know better. We just need to put them in their place.”

“I… thought we were a free land… free from laws.” Guybrush spoke up quietly.

“And we are. But we need some… guidelines for the colonists.” Tew replied.

“O-oh…” He shrunk back in his seat and listened in to the rest of the conversation. There was a sense of dread brewing but Guybrush tried to ignore it.

Elaine strolled through the streets of Libertalia, silently thankful that she wasn’t as recognizable as her husband and the other Founders were.

She appreciated the home Guybrush provided for them but she left that lifestyle to be with him, and yet there she was… stuck in that God forsaken mansion alone with just Winslow (who took no offense and would often times find himself at the local bar). The town was just as bursting as ever with people going about their days, some looking for their husbands who no doubt were probably behind an alleyway drunk, and some sitting back and swinging some grog.

And the jail cell, which was suppose to hold the rowdiest of drunks slowly became more filled with pirates that reminded her of that one former crew-mate of Guybrush… what was his name? Oh right! Otis. But Otis wasn’t a drunk, that much even Elaine and Guybrush could agree on. So why was it becoming more full lately?

Libertalia was starting to feel… eerie.

"Rebels?” Guybrush asked.

Elaine nodded. Often time she passed an area and she would hear whispers, but as to what, she couldn’t make heads or tails of until one day she saw what looked to be a skull and a massive ‘X’ and heard word of the colonists feeling angry.

“But… but we didn’t steal their money.” Guybrush explained. “It’s like… a communal bank or something… I can’t really properly explain, I know.”

“Maybe… in the next meeting, ask the other’s about it. Not the rebels, I could’ve been hearing things, but regarding the treasury.”

“Y-yeah… yeah, I’m sure there’s an explanation.”

She was glad he was still willing to listen to her even after the Founders told him otherwise.

He couldn’t believe what he was hearing.

“But they haven’t DONE anything!” Guybrush argued.

Edward England barked a laugh. “Boy, what would YOU know?”

“I know that if colo– ANYONE would be upset if their money was TAKEN from them in secret for someone else’s selfish gain. Imprisoning them and then not even having the courtesy to tell them of what they’re being held is just adding more fuel to the fire. Even a monkey such as yourself knows that!”

“You bite your TONGUE, Founder Threepwood, or I’ll have it ripped out myself!”

Guybrush didn’t flinch. No one was going to hurt his citizens… not on his watch.

Whispers turned to loud conversations. Guybrush, Elaine, and Winslow couldn’t deny it anymore they could feel the tension between the Founders and the colonists slowly but surely bubbling. For his own safety, or rather, for the safety of his people, Guybrush stopped walking the streets of Libertalia. The last thing he wanted to do was instigate a war before he could properly calm down the situation down.

Guybrush felt stuck between a rock and a hard place.

On the one hand, he understood the frustration the colonists were going through, who wouldn’t be angry that their money was being taken from them?

But on the other… as a Founder… he has their best interests, but in their eyes it didn’t feel like it. And as one of the leaders, it would be wise to not intervene.

This sucked.

“The attacks are getting worse.”

“I know.”

“So you’re just going to leave them be?”


“No what.”

“I’m not… I can only do so much without having someone getting near me to put a bullet between my eyes from both colonists and the other Founders.”

“You’re admitting defeat.”

“I’m not– Elaine. Just… stop. Please.”

Guybrush was changing right before Elaine’s eyes.

The confident and optimistic personality soon shifted to a more subdued and stern one. His usual quick-witted retorts that were already far and few in between vanished all together. His warmth that he usually radiated was just a memory. And that light in his eyes that showed hoped was fading rapidly to that jaded cold stare.

He would be up late into the night trying to think of anything to help the people, but the more he heard of them speaking ill of him and the other Founders, the less he felt the need to leave New Devon. And the Founders sure as hell were making it worse by shouting and yelling at him to join them with THEIR gold. It was getting at Guybrush more and more, and with each day he the less hopeful he felt that he COULD help either of them.

Elaine worried for Guybrush’s sanity as she felt Libertalia breaking him.

Guybrush ran through the jungle path that only he knew of as he managed to sneak out from the bloodbath that was going on in the Treasury. Stupid Founders and ungrateful Colonists be damned– no. No stop. That’s not what you mean.

This isn’t you!

He collapsed to the floor trying to breathe, but the smoke he inhaled from the cannons and the fire was overwhelming and his coughing scratched his throat badly. How? How could this have happened?

The colonists were shouting for the Founders’ heads, demanding their money back as it rightfully belonged to them, and most of all reclaiming THEIR Libertalia while the Founders were too busy murdering one another for the damn gold.

He didn’t care. He didn’t care anymore. He just didn’t care about any of this anymore. He didn’t–


He cared about her. She was the only one he cared about. Her and Winslow. They were his rock and seemed unaffected by greed.

Shakily picking himself, Guybrush tried clearing his throat once more before he began running towards the guarded community.

This wasn’t suppose to happen.

“Guybrush?!” Elaine shouted as Guybrush barged into his house and quickly slammed the mansion doors behind him, sliding down and panting heavily as he reeked of gunpowder, blood, and sweat. Elaine didn’t need to be told twice what happened and quickly rushed to his side, hearing the other footsteps belonging to Winslow.

“Guybrush. What happened. Talk to me.”

“Be ready to leave at any moment… I… Libertalia and New Devon isn’t safe.” Guybrush hoarsely instructed, but it was clear he was barely holding it together.

She didn’t question him.

“Founde– Annie. Please. Listen to me, this isn’t what we wanted. You and I both want the same thing. We both want a place for pirates everywhere. We’re better than this!” Guybrush pleaded, trying to talk SOME sense to any Founder willing to listen or have a resemblance of a heart.

Bonnie scoffed. “And I should listen to you because?”

“Because you and I both know all this gold obsession? This is insanity. And you’re better then this.”

She remained quiet.

“I’ll think about it.” Bonnie answered.

A small glimmer of hope.

The mansion became riddled with holes and burn marks, but those who lived inside were still alive. New Devon became a war field and Libertalia was caught in a tragic Civil War that could’ve–should’ve been avoided. Winslow held tightly to his flintlock while Elaine made sure to avoid any open doors or windows to the best of her ability.

Guybrush… just looked to be stuck in thought. Clutching his cutlass like a lifeline while he stared at a parchment signed with Tew’s insignia.

The sense of dread was now bells and whistles going wild for both Elaine and Guybrush.

And yet… he remained quiet.

“I’m… going to talk with them. With the Founders.” Guybrush spoke quietly for what felt like the first time in days.

“What?!” Winslow gasped.

“Guybrush you can’t, this could be a trap!” Elaine frantically countered.

“I-I know… but if there’s even a slight chance that I could change their minds, if I could somehow stop all of this… I need to do this.” He practically whispered, his voice sounding shaky with nerves… like he was scared. “I… if for whatever reason this doesn’t work I– please. Flee Libertalia. Don’t look back. Help the citizens escaping if you can. I need to know you’re all safe. That you two are both safe.”

“Guybrush I– you can’t.” Elaine begged. “I can’t… I can’t let you do this… I can’t lose you. Not again.”

“I’ll promise you, I’ll come back.” He promised, giving her a kiss on the lips before walking out the door.

“Guybrush, wait.”

The blond stopped and turned around.

“I… I love you…” Elaine choked up.

For the first time in years, she saw that small glimmer in his eyes and Guybrush smiled back.

“I love you, too.”

Hours passed and Elaine and Winslow fled the mansion under the full moon light. Guybrush was smart. He would know how to find them, Elaine kept telling herself, biting back any tears that burned her eyes. She couldn’t cry. Not now. She didn’t have a reason because he was still alive. He was just busy and all those meetings took forever and–

“Mrs. Threepwood.” Winslow whispered, cutting through her thoughts.

“Oh… I um… my apology.” Elaine muttered. Wiping away any tears she felt slip past her guard. She just wasn’t able to shake off this feeling that she was never going to see Guybrush again.

“He’ll be alright. He always finds a way back to you.” Winslow reassured, gently rubbing Elaine’s arm. She nodded.

“You’re right… I… you’re right.” Elaine nodded. “C'mon, we need to help the others.”

They made their way to the town to help the families caught in the crossfire trying to escape.

The other ships made their way out, the families, pirates, and other refugees thanking Elaine and Winslow profusely for helping them, some even being instructed to head towards Melee or any of the Tri-Island area.

“Mrs. Threepwood, we need to get going.” Winslow pointed out.

“We will, but I just… another couple of minutes. I don’t want to leave Guybrush here.”

“But ma'am… he said–”

“I know what he said!” She covered her mouth and took a deep breath. “I… I’m sorry I just… I don’t want to leave knowing he has a chance to escape.”

Winslow remained quiet.

“I’ll keep the Narwhal here for another hour. After that…”

“Very well, Mr. Winslow.”

Please… please come back, Elaine silently pleaded.


Chapter Text

Ending - General

The further he walked away from the mansion, the more numbing feeling would creep over him. He followed the instructions and made his way towards Tew’s mansion, where he and a bunch of the other Founders would gather and speak like rational men– no, Bonnie wasn’t a man, like fellow PIRATES about all of this mess.

But that dread… it lingered and he couldn’t push it away no matter how optimistic he tried being.

The tension simply standing by the doors was unbelievable. All the Captains had a hand on their belt, very clearly to draw their weapons at the ready if need be. Guybrush kind of regretted not having a gun on him just in case, but using that kind of weapon wasn’t in his nature. A cutlass? Yes. A flintlock? …No.

And besides, if things went accordingly, his only weapon he’ll need to draw is his words. Because if there’s one thing Guybrush can do that the other’s cannot, it’s talk.

Well… at least better by a smidge.


The dining room was dimly lit, there wasn’t any meals there to even snack on but Guybrush figured they would be too busy talking to eat. Mugs, however, there was exactly twelve of them and they were all placed around the table next to a card that had the image of each Pirate Captain’s sigil.

His ship was called the Screaming Narwhal, and yet his sigil had to be a monkey. Of course. THAT made sense– no. No. Focus. 

Guybrush took a seat at the far end of the table, facing Avery head on as the other pirates sat where their cards were, either angrily glaring at someone or remaining frightfully quiet… calculative, even. Even if Guybrush came for peace, he still kept his guard up. Better safe then sorry.

It was then when he heard the doors opening, and in walked Thomas Tew and Henry Avery.

The meeting was about to begin.


Uncharted Ending

“A toast to Libertalia!” Avery raised his chalice up, allowing the lights to glisten against the drink and various rings on his fingers. The other Founders also raised their mugs, Guybrush included. It seemed like Henry had SOME common sense, after all.

“For God and Liberty!”

They all chanted along side before taking a swing of their drinks when Guybrush felt his heart stop. 

This drink… this wasn’t grog or wine. Hell, it wasn’t even the sugar-coated disaster of a libation like he had back in Flotsam. This tasted… tasted like–


He dropped his chalice and grabbed his throat, feeling himself being choked from the inside as it burned. The other pirates around him all collapsing on the table, gasping for air and trying to curse Tew and Avery who appeared to have not even take a sip from their drinks and instead stared at them all with a disgusting smile on their face.

His vision was blurring, but he saw them stand there like the fucking pigs that they were. Those bastards. How could they?!

How… how could HE have been so stupid? Trusting Avery… he should’ve known better. The man was known as scum and yet… two times he fell for someone like that.

The gasping was all slowing down as one by one each of the pirates stopped breathing and he could feel his time rapidly coming to an end but he tried standing up. He couldn’t die here… not now… not when he promised Elaine he’d come back. He promised her. He couldn’t break that promise again. 

Guybrush fell back in his chair, his body no longer functioning and tears pouring. What he’d give to see her one more time… to tell her how much she means to him. He couldn’t even speak anymore.

He closed his eyes, desperately hoping that maybe this was a nightmare… that he’ll wake up back on the Narwhal with Elaine and Winslow, sailing off to the horizon… what he’d give to go back and gave his last breath before collapsing.

‘Elaine, I’m sorry.’


Alternate Ending 

“For God and Liberty!”

They all chanted along side before taking a swing of their drinks. Guybrush nearly took a sip when something about the smell didn’t feel right. Before the drink could touch his lips, he lowered the chalice and gave it another sniff. No… no this wasn’t grog or even that terrible red wine Elaine occasionally drinks, no this was…

“Poison!” Guybrush gasped, quickly throwing the lethal drink as far away from his possible, looking up and saw the other Founders gasping for air and dropping their own drinks. 

“W-what. Why?! WHY ARE YOU DOING THIS?!” He shouted as the two older men stared at him angrily, with a feral look in their eyes. He frantically scurried out of his chair when he saw Tew and Avery pull out their weapons.

“Because the money… is our’s. And you’re a thief.”

“W-w-w-w-wait! WAIT!” Guybrush pleaded before barely dodging a gun fire from the diabolical Founders and running out the door. 

He ran as fast as he could out of Tew’s mansion, not daring to look back as he heard footsteps following him as one of them barked for their men to go after him. 

How could he have been so stupid?! So blind?! Of course they were in for the treasure, they’re… they’re… they’re fucking PIRATES!! Goddammit, he felt stupid. 

There was a loud bang as Guybrush just barely dodged another bullet making his ears ring.

Gotta keep moving.

He ran towards the jungle, the moonlight acting as his only source of light. When he gets out of here, he will NEVER trust another pirate aside from his own crew ever again. Never again. 

There was yet another loud bang and something hot pierced Guybrush’s thigh, causing an anguished cry as he fell down holding the wound, the growing dark red stain was seeping through his pants as he clutched it desperately to try and slow the blood down when he heard the other crewmen shouting.

No… no. No he can’t… not like this. He can’t die like this.

“Where did he go?!”

They… didn’t spot him?

“Search the area.”

He lowered his body into the high grass and drew out his cutlass. He had a chance to escape.

He lost track of time but he somehow managed to crawl along the dirt and avoided being caught. Slowly standing up, Guybrush planned out the pathway from New Devon towards where all the ships were. If he was even remotely lucky, he could find a rowboat, if that. 

Rushing to his former mansion, he scoffed at the sight. How stupid of him to think Avery had his best interest. No… not now. Find the ships first, hate yourself later. 

He jumped through the passageway he told Elaine about in case of any emergency. 

Guybrush clutched his thigh. It felt like it was on fire with each step he would take and he was positive crawling around in the dirt did little good to the wound. ‘Stay focus. Don’t lose sight.’ He mentally chanted to himself. He needed to focus. He needed to escape. Avery was out of his damn mind and like Hell he was going to stick around to see the man burn this island to the ground. 

His eyes burned and his stomach churned at the notion.

This wasn’t suppose to happen.

It felt like hours but soon he saw the series of torches and the bright full moon. He did it, he made it!! A gasp in relief as he took a step forward when he heard the sound of a sword being unsheathed. Not wasting a second, Guybrush turned around and quickly drew out his cutlass, countering the deadly weapon that was aimed at his head.

One of Tew’s men found him and there was bloodlust in the solider’s blue eyes contrasting the fear in Guybrush’s.

“W-w-wait. I-I’m sure we can discuss this like civilized men–!”

“Shut up!”

The solider swung his sword once more but Guybrush was able to counter him. He was known as a fearsome swordsman for good reason, but even he was human and always wanted to give his opponents a chance to backdown. 

“Look, I don’t want to hurt you!” Guybrush warned a second time. It fell on deaf ears as the man swung once more, this time slicing Guybrush in the side forcing Guybrush to cry in pain.

Not wasting another swing, as the man raised his sword up, Guybrush ran his cutlass through the man. “I… I’m sorry… I’m so sorry…” He whimpered as he heard the sword dropped. He pushed the body off his sword and stumbled back, clutching the now growing stain on his shirt. 

He took off the blue coat and draped it on the solider. The man didn’t LOOK like Guybrush from up close, but from far away it was enough to deceive the unobserving pirate.

Hopefully Avery and Tew will leave him alone.

Everything was becoming dizzy, but he had to keep moving… he wasn’t about to die here. He wouldn’t allow it. Not when… not when he had a promise to keep. Guybrush saw from the distance all the other ships escaping the rioted Libertalia. He had to look away, the sight was just as painful as his wounds and right now he couldn’t afford to stop. 

Looking at the harbor, he spotted on familiar ship. It’s run down constructed by sorts-look was still there… he could cry.

It was his home. 

And hopefully his family was there too.

“Mrs. Threepwood… it’s about time…” Wislow said sadly as he raised anchor. Elaine clutched her hands together, almost begging whatever it was watching over them to look for her husband. But it’s been an hour… and she promised him they would leave.

“I… alright…” Elaine spoke sadly when there was a sudden thud against the ship’s deck followed by a moan. Winslow drew his gun quickly but Elaine put her hands up to prevent the first mate form shooting.

“Wait wait!!” She pleaded, grabbing a lantern and putting it over the bloody looking corpse. Elaine squinted her eyes before it widen in shock, covering her mouth to suppress a loud gasp.


He couldn’t speak and could barely open his eyes, but Elaine held him in her arms, brushing back the strands of blond from his face.

“Stay with me… stay with me Guybrush, it’s alright. You’re safe…”

Winslow eyes widen and rushed over, but before he could kneel, Elaine ordered for him to get them out of Libertalia now as Guybrush fainted.

“For God and Liberty…” Elaine growled.

To Hell with it’s Founders and to Hell with Libertalia.

Birds were chirping and sun beamed down from the window to his face. Guybrush winced a bit at the light and slowly opened his eyes. High above him wasn’t a decorative ceiling made of stone and marble, but rather of wood. Funny, he thought he didn’t live in a wooden house anymore– wait.

He quickly sat up only to feel his body emit a wave of pain from his side, causing Guybrush to wince and clutch the wound that was bandaged. 


He shifted his body from the creaking bed and placed his feet on the wooden floor, pushing his body up until there was a shot of pain that came from his thigh causing Guybrush to crash on the floor and cursing in pain. 

Guybrush looked around. This… wasn’t the Narwhal. This wasn’t New Devon. So was this Libertalia?

No… Libertalia fell. As did the other Founders, that dream of a safe haven, and the chance of doing something right in his life for other pirates.

His throat felt tight and he remained on the floor.

He failed.

But he was alive.

And he didn’t know which felt worse.

Elaine rushed in at the sound of the crash, spotting the blond curled up on the floor. She quickly kneeled down and lifted the blond to sit upright, noting the bloodshot eyes and red nose and embracing him tightly. 

“It’s okay…” Elaine assured softly, brushing back his hair as she felt him shake and holding on to her tightly like she might disappear. 

“It’s okay.”

It’s been a few weeks since she, Guybrush, and Winslow sailed far away from Libertalia and even the Caribbean to a new region. As to where, she didn’t know but Elaine trusted Winslow to find them somewhere quiet or at the very least, where no one has heard of the dystopian island or of Guybrush. Of course the man did just that, even going to so far as to give Guybrush a quick patch up until they could find a proper medic. 

Guybrush didn’t take to waking up all that well, but it was to be expected. She would’ve honestly have been more surprised if he just brushed it off but Elaine could tell that the fall of Libertalia was eating at him, leaving him to be more and more a shell of himself but the tranquility of the town… he was still there. Just faintly.

She and Winslow made it their business to not make mention of it ever again.

By the cliff side, Elaine spotted the blond sitting and staring at the sunrise over the ocean, his cane laying next to him unattended to. How he hated that wooden stick with every fiber of his being, but he knew that without it, he would practically be bounded to a wheel chair based on how he couldn’t walk too far before he either fell or the pain would get the best of him. And THAT pissed him off more.

“Room for one more?” Elained asked, snapping Guybrush out of whatever train of thought he was in. He looked up at her and scooted a bit to let the red head sit next to him, not flinching as she rest her head on his shoulder, wrapping and arm around her. 

“What were you thinking about?”


“You looked to be in thought.”

“Oh… um… nothing, really. Just the usual cacophony of things.” Guybrush answered truthfully. 

There was more silence.



“I love you.”

He remained quiet, she could hear his thoughts of guilt shouting at him before he gave her arm a small squeeze.

“I love you, too.”

Chapter Text

The room was dark and empty, hearing nothing but the echoes of his boots touching the marble floor. Guybrush looked around for any source of light so he could see where he was when a torch lit up next to him followed by a series of them all leading him to a massive dining table.

“What the…?” He muttered, taking a step closer until he froze in place. The Founders all sat there, a chalice in their hand and a smirk on their faces, raised to toast to push aside their animosities and for Henry and Tew for reuniting them all.

“W-wait… wait STOP!! IT’S POISONED!!” Guybrush shouted, reaching a hand out for Anne Bonnie who turned to nothing but a skeleton the moment he laid a hand on her. “N-n-no… no this isn’t… this isn’t happening this isn’t what was suppose to happen I–”

He froze when he heard the sound of a gun cocking back. Tearfully looking up, he stared down the barrel of the flintlock the now skeletal Henry Avery was holding in front of him.

“For God and Liberty" Avery mocked and pulled the trigger.

The weeks turned into months since the fall of Libertalia but it felt like a lifetime ago since anyone has made mention of the hidden city. Guybrush hobbled around the town, noticing the people living their lives ignorant of what transpired on another island. He was silently thankful as it meant that it was only a matter of time until no one except for Elaine, Winslow, and himself would’ve known about it’s existence. Soon that island would be nothing more than a forgotten nightmare.

If only the island could let him go. 

The inn they were staying in for the last few months was nice and all (and it helped immensely that Winslow knew the owner on a personal level so they didn’t need to pay) but Guybrush felt himself being called back to the ocean. He knew why they couldn’t go back to the Screaming Narwhal, but as much as it logically made sense, being stuck on land felt like a death sentence. 

An exaggeration, sure, but he wasn’t one to enjoy staying in one place for to long. 

“Easy steps now, love.” Elaine assured, her hand behind his back as he took small steps. He was determined to get better so he didn’t need to use that God forsaken stick and finally prove he can go back out to sea. She saw him gritting his teeth, biting back the obvious pain the bullet wound left him with before she saw him lock up and stumble, landing hard on his knees and hands. Not missing a beat, she pulled the cane he placed to the side and bent down, holding it for him to hold while placing a hand on his back.

“You’ll do better tomorrow. C’mon, let’s get you up.”

She heard him mumbling something in frustration.


“I said I’m fine.” Guybrush barked, causing Elaine to jump back a bit. There was a long silence before he sighed. “I… I’m sorry…”

He eyed the supposed temporary cane which felt more like handcuff that was mocking him and looked away.

He hated it.

Fresh air. He needed fresh air.

He found himself sitting on a bench in the middle of town square, or at least, this island’s idea of a town square as the morning kept replaying again and again in his mind. He couldn’t walk. He just couldn’t WALK. His leg kept failing him that even the doctors told him it would be best to just become adjusted to the wooden stick and out of sheer frustration, he tossed the cane to the other side of the room, almost positive he broke something in there but in the heat of the moment, he didn’t care. He couldn’t stay in that fucking room another minute otherwise he was going to scream. 

And yet.

There he was in town.

Holding on to that fucking cane.

Guybrush was being mocked, he was sure of it.

Soon the locals became familiar with the blond pirate. Or at least, as far as they were concerned, a simple sailor. He tried keeping his distance from them, he couldn’t go through that heartache again of knowing the citizens, but in the end he found himself waving at the people that bid him a good morning, afternoon, and evening. Sometimes they would ask how’s the weather from his height, how was Elaine or Winslow, or any tips for sailors about to go off at sea. Some asked how his leg was feeling and offer him some ice or anything to ease the pain.

Everyone here treated him so kindly, welcoming him with open arms. And it ate Guybrush up from the inside. 

He didn’t deserve this.

The months began to blur and the self hatred was, while still lingering, beginning to slowly subside. Guybrush enjoyed hearing about the baker’s wife and her problems of what to cook for the next book club (which, according to her, he should part-take in one of these days). He didn’t mind handing the cane over for the kids to play whatever make-shift game Winslow invented. He enjoyed chatting with the local sailors that returned from recent trips and hearing about how the ocean life was fairing.

The small voice in his head, however, was shouting how he didn’t deserve this. But he kept trying to push it down for his own sanity.

If he was lucky, for a few hours of his day he could actually feel like his old self again. 

Elaine saw him everyday sitting by the cliffside staring out at the ocean almost longingly. She couldn’t blame him. Ever since Libertalia’s fall, she and Winslow basically locked Guybrush to some other hidden island almost banning him from going near the ocean out of fear that any Libertalians might spot him. 

She nearly lost him during that war, she couldn’t risk that chance of losing him again.

Still, something deep down was telling her that by holding Guybrush back, it was slowly killing him. No matter how much Guybrush would smile to the locals, it wasn’t really HIM smiling, just a phantom of the ones he used to give. But he would always go back to that cliffside and look at ease.

Happy, even. 

And only then would she actually SEE Guybrush.

“Are you sure you want to buy this shack?” The local asked with his arms crossed. “I mean, it’s not… big enough, y’know? It’s good for a weekend, if that but not to live here, plus I don’t think anyone has cleaned it up in years.”

Elaine and Winslow walked in the run down shack and eyed the place as the wooden floor creaked with each step. It was definitely smaller then what they were use to, and more than that, it was just a good few feet tighter than the Narwhal.

But it was the sounds and sight of the ocean from the kitchen window that made Elaine smirk.

“It’s perfect.”

“Can I open my eyes now?” 

“Juuuuuuust a bit, Picarooni.”

“I– c’mon, Elaine.”

“Okay, now!” Elaine removed her hands from over Guybrush’s eyes who had to blink to adjust to the semi-dark room due to all the closed blind windows when he looked around.

“It’s… a shack.” He answered, looking at Elaine confused. “I don’t… I don’t understand?”

“The best part is out that door.” She smiled as she pointed at the back door in the kitchen. Guybrush looked between his wife and the door before walking over and opening it, covering his mouth to suppress a gasp. He looked over at Elaine, wondering if he was dreaming but she just nodded.

“Well, go on.”

He took a hesitant step forward, hearing the soft crunch of the sand emitting from his boots, feeling the sea breeze softly brushing against him as the seagulls cawed from above him. He walked over to the shore and watched the waves crash rhythmically into the sand.

Shakily with one hand still holding his cane, Guybrush took off his boots one by one and tossed it to the side, letting his toes feeling the sand underneath. How long has it been since he felt the warmth beneath his feet? Looking at his cane, he tossed it also to the side and took a step on the wet sand, letting the ocean crash into him, feeling the wet sand escape from beneath him. It was warm yet refreshing. 

Like being home.

His breathing hitched. 

For the first time in decades, he felt like himself.

After several weeks of pestering and asking, Guybrush eventually gave up. It was apparent Elaine wasn’t about to reveal how she was able to get a home like this and instead suggested that Guybrush simply enjoyed what they have followed by playfully bopping him on the nose. 

Granted, he would pout every time she dodged the question and occasionally would make a point that they might as well be living back on the Narwhal (in fact he loved to openly point out that the ship’s deck was bigger then the kitchen). 

But in the end, he did truly love their new house.

“Elaine, please? Just this once.” Guybrush asked.

“Guybrush, I insist, it’s alright it’s no bother to me.” She leaned her back on the counter staring at the puppy eyes that was Guybrush’s. For the past few weeks, he’s been limping around the kitchen always asking Elaine or Winslow if they needed help. Of course, they would always say no and then point him to the couch to rest to which then he would cross his arms and pout. Today, he seemed hellbent on cooking. 

“All I need you to do is just relax.” Elaine insisted.

“It doesn’t even require that much movement, just standing a bit. I can do that. I’m good at standing!” Guybrush practically pleaded. “Please? I… I want to help. Please.”

There was a long pause before she just sighed in defeat.

“Alright. Just this once.”

Guybrush pumped his fists in the air.

Never in her wildest dream did Elaine Marley ever imagined this was going to be her life. Living in a small shack by the sea, married to a pirate (ah-ah… Mighty Pirate™) doing laundry. Not that she was complaining, if the circumstances were different she might’ve had a different attitude, but as it stands she didn’t mind it. Carrying the basket of clean clothes, Elaine hoisted it over to their bedrooms where she spotted the familiar cane resting by the drawer as a lanky blond was fixing the bed sheets. 

Or at least, ATTEMPTED to fix the bed sheets. 

Guybrush was currently sprawled like an octopus grabbing at all three corners trying to get it to go to their respective corners. She should’ve told him to knock it off and rest but for a split second, she was reminded of a time long ago.

“You know… most people do it one at a time.” Elaine spoke up, resulting in Guybrush giving a startled yelp.

“I ah… I know.” He blushed. “It’s just been a while since I did this… um… I’ll have it fixed in a minute.”

Elaine giggled.

Within a couple of months, a routine was formed. Winslow would go out and gather whatever supply they needed from the town square, Elaine would prepare the meal based on said ingredients, and Guybrush would either jot around in journal, get some therapy in, and then go to their backyard to sit by the ocean. They would all pitch in with cleaning up the shack and doing the dishes and make their beds whenever it was deemed needed.

Occasionally they would shift around and Elaine would gather the supply and Winslow or Guybrush would cook. Both she and Winslow agreed that Guybrush wasn’t allowed to gather supply. Not because they were worried for his leg (although it had some part in the decision) but rather he couldn’t pick the correct vegetables if his life depended on it.

It was a very simplistic life, but all three were content with the quiet.

Since they moved to the shack, Elaine had taken noticed in the drastic change in Guybrush’s mood, silently kicking herself for not thinking of it sooner to move near the ocean. Granted, he wasn’t back to his old self pre-Libertalia, but there were moments where it almost felt like that entire time in their life was a far off dream. 

But then there were times where he just couldn’t walk without his leg feeling like it was on fire, his growing frustration when it happened, and the night terrors.

God, the night terrors.

How she wished she could find a way to end those nightmares once and for all. It killed her inside every time he woke up screaming, covered in beads of cold sweat, begging for forgiveness and mercy from the nightmares. And all she could do was hold him tight and reassure him that those dreams can’t hurt him. 

And yet she felt that it was already doing just that.

Guybrush sat on the shore, watching the waves crash in in a hypnotic motion. He heard the sound of talking and briefly looked over his shoulder and saw Elaine by the kitchen most likely whipping up another meal while laughing as he heard Winslow cracking another one of those suggestive jokes that turn Guybrush’s face red. He couldn’t help but give a small smile.

He missed hearing them laugh. 


“Yes, Threepie?”

“Do you… do you miss going out at sea?”

She remained silent. Part of her knew Guybrush was trying to find a way to stay awake to avoid sleeping while the other part was a genuine question.


God, how she missed that nickname. 

“Sometimes, yes.” She admitted. 

“O-oh… would… would you go back out there if given the chance?”

Her heart sunk. She turned over to look at him in the dark room, the only thing she could see was his silhouette thanks to the moon peering between the curtains, and held his hand tightly. He wasn’t shaking, but she could hear it in his voice.

“Only if you’re there with me, Guybrush.” Elaine reassured. 

She heard a small sigh but she couldn’t decipher if it was of relief or sadness or both.

“You know you don’t have to stay with us. I can’t… I don’t want you to feel obligated. If you want to go, you’re more than welcome to. I promise I… I won’t be mad.” Guybrush spoke solemnly to Winslow. The portly first mate simply sighed and moved his cup of tea to the side, leaning his arms on the table and looking at Guybrush in the eyes.

“Oh, I’m not leaving.” 

“But Winslow, I–”

“Sir. I’ve told you once, and I’ll tell you again. I’m not leaving. Not now. Not ever.” Winslow answer firmly. “After everything we’ve been through, you and Mrs– you and Elaine, you two are my family now. If you think for a second, That I’m willing to leave you because I want to sail or feel like I’m being held back, then you clearly don’t know me very well. I spent two years stuck on Flotsam against my will. I WANT to stay with you for as long as possible.”

Guybrush began to shake. Winslow walked over to the blond and began holding him tightly in an embrace.

“You’re stuck with me, whether you like it or not, Captain Threepwood.”

Winslow rubbed Guybrush’s back as the blond choked up.

The sun beamed down on the ocean, making it look like it was a ginormous glistening gem. Guybrush sat once more by the shore as he did every day and watched it crash, taking a giant breath as he smelled the salty air. That’s it. Today was going to be the day. 

Guybrush used his cane to stand up before dropping it to the side as he felt no need for it at the moment and hobbled over to the ocean, feeling the waves crashing into his bare feet. Soon the water rose up, feet, ankles, shins, thighs… he braced for the pain that never came as the waves soon went up to his hips, feeling the waves rocking him momentarily. 

Before he could go further, he heard Elaine calling his name.

Some other time, he figured.

Once the sun began to set, Elaine was always found in the tiny living room reading a book by the candle light. It was her downtime when she wasn’t keeping an eye on a particular blond pirate and both Winslow and Guybrush respected that. However, occasionally she’d fine her husband resting his head on her lap, unbudging, holding her free hand with his ringed one and staring at it as his legs dangling over the tiny couch while she played with his hair, her eyes fixated on the book in hand. 

It was a humorous reminder for Elaine of Guybrush’s height.

But upon closer inspection, he only ever did that for one of two reasons: Either he was bored and wanted to be affectionate or he was trying to distant himself from something. And as of late, he’s been far more reserved then she cared to admit.

She figured it was the latter and continued their little tradition, feeling him shake slightly on her lap.

“Okay… just like riding a bike…” 

He stood in the ocean at his hips and took a deep breath before he dove into the water. 

Ten minutes.

Slowly, he opened his eyes and saw the brimming ocean life as a school of fish swim by him, the brightly coral reef almost blinding him with their vivid colors.

Nine minutes.

He swam around, feeling the sand dancing at his finger tips and seeing a fish the size of his hand look at him with curiosity before swimming off.

Eight minutes.

Guybrush swam as far as he could until–

“Nrrgh!!” He winced and grasped his thigh, feeling the ache radiating. No. No nononono… please. Not now. He mentally pleaded. 

Six minutes.

He looked up and saw the ocean life, pushing past the pain and continuing swimming. His leg was on fire but he didn’t care. He could do this.

Five minutes.

Eventually he saw the end of the line. Not because of his thigh or his time limit, oh no. It was just… dark ahead of him. And he knew he needed a boat to see further on. And at this point, he didn’t know if he was going to be on a boat.

Four minutes.

Well, there was nothing left to see, and it felt like the pain was gone for now. He looked up and saw the sun dancing on the surface of the water. 

One minute.

Guybrush kicked himself up from the seafloor and emerged on the surface, taking in a bit a of breath before lying on his back on the water, letting his leg rest from all that swimming. ‘Guess I’m out of shape.’ He joked to himself. Maybe, one day, he’ll be back on his ship, sailing the seas and swimming to his heart’s content. 

His thoughts fell quiet after a while, leaving him to hear the waves crashing into the shore, the birds cawing, feeling the sun beaming warmly on his face, and the ocean rocking him slowly.

On the plus side, he still had his ten minute limit. 

That’s always a good thing.

Chapter Text

Henry Avery leaned back in his chair, his hands resting nicely on his stomach as he eyed the blond sitting parallel to him with only the few lit candles in the bar to illuminate the two men. “You have determination. I respect you for that. Not many pirates can push passed the desire for greed for their own self gain. So tell me, Threepwood…” Henry then leaned close, the fire reflecting in his eyes, “How would you like to join me in Paradise?”

A startled gasp. 

Guybrush opened his eyes to the sun beaming down on him and the waves currently holding him afloat. His breathing was fast and he quickly pushed himself to float up-right, a hand over his chest as he tried to steady himself.

It was just a memory. A distant… distant memory.

The seasons came and left and time soon became a whisper, but if Elaine had to wager a guess, it’s been probably well over a year or so since they fled Libertalia. She could only surmise as such when she noticed the chill breeze of winter one morning and a particular blond pirate sat on the shoreline shivering and pouting. The water must’ve been too cold for him, she thought. 

She remembered the first winter they spent in their new home, he asked why not just sail out to some place warmer, they had the ship, it wouldn’t be an issue. But instead it was just met with Elaine staring sadly and quietly telling him: “You know why.”

And he did. She knew he did. Didn’t stop him from clutching his cane tightly almost in anger and walking away feeling defeated.

He quietly sat on the shore, watching the icy waves crashing against the shore. He could hear it calling his name, enticing him to go into the water… and if he was going to be honest, Guybrush was tempted. The only thing holding him back from risking a dive was the fact that it was winter, and he was currently comfy sitting on the shore huddled in his blanket staring bitterly at the ocean.

Still… couldn’t hurt to try. Vikings swim in icy waters all the time, right?

Guybrush stood up and slowly took off a single boot, already regretting it as he felt the wind nip at his toes. ‘Take a deep breath, Threepwood.’ He told himself carefully dipping the big toe into the ocean and immediately retracting back and falling on his behind, cursing up a storm. Nope. Terrible idea. Putting his shoe back on, he hobbled back to the shack.

It was too goddamn cold to even put his feet in.

Elaine never asked what happened to his coat. When he landed on the Narwhal covered in sweat and blood that night, she noticed his blue coat that was always two sizes bigger than he was was missing. She thought of asking him when he woke up where it was, but when she saw him there on the floor that morning looking like a broken and miserable shell of himself, she decided it wasn’t important. His coat may have been missing but it felt like so was her husband.

She looked to her side and saw Guybrush sitting next to her practically cocooned in a blanket by the fire place with his journal and pencil in hand, looking a little bit like who he was before Avery. Back when he was focused but at ease.

Small steps, she thought to herself.

“Remind me again why we’re here?” Guybrush asked.

“Need to get some things for the house.” Elaine answered. 

The two walked into town that looked to be busy with preparations based on the decorations around the main town square with Elaine holding his arm while she also held on to his cane, allowing him to feel like himself for a bit by leaning on her. Ever since they moved to the shack, Guybrush barely visited the town square, opting for solidarity over strangers. 

“So… why me and not Winslow?” He continued asking.

“Well for starters, WE’RE married. Not me and Winslow.”

He blushed embarrassingly.

“Also because you’ve been cooped up at home for too long, an outing where there’s people is a good thing for you, Guybrush. You… you need it.”

Guybrush fell quiet, understanding what she was trying to do. 

Elaine gave his arm a small squeeze as she felt him starting to limp. She had another few minutes before he’ll need the wooden stick. “Now come along. I want to get something.” She guided Guybrush to a shop. The blond looked confused but went along anyways.

He sat on a bench while Elaine was in one of the stores. Guybrush tried keeping up, but eventually his leg won over his wife and resulted in him being benched. This was embarrassing, Guybrush thought. Taking a breath, Guybrush began watching the people running from store to store, arms carrying bundles of items from food to cloth and everything in between. Some chatted with one another, others gave a brief hello and byes and ‘say hi to the missus for me’. 

Guybrush leaned his chin on his cane as he continued to watch the people walk by him.

He wasn’t resentful for them living their life and was admittedly jealous of the locals for being so blissfully happy and content himself. And who was he to tell them how to feel? If anything he’s the stranger to their home, they’ve shown him nothing but kindness. They always walked up to him first and initiated the conversation. Of course, that wasn’t to say he completely ignored them. Guybrush talked with the locals, but he always kept some kind of distance, never talking about himself or actively starting conversations with them. 

He always felt like an outsider.

But maybe one day he’ll embrace this island as his home and no longer feel foreign.


He winced in pain as he rubbed his thigh sitting next to the fire place. He already wasn’t a fan of the cold but now he had more of a reason to hate it as it made his leg act up in such fierce pain that he couldn’t move without it flaring up. And walking the whole day sure as hell didn’t ease it.

“Here, this should help.” Elaine spoke up, placing a hot rag on the wounded thigh. 

The initial placement caused Guybrush to hiss before sagging his body in relief. “Thanks, Laineykins.” He soon said as he rested his head against the edge of the couch, feeling the pain subside and Elaine playing with some strands of his hair. On every account, he had something to kvetch about, but in that moment his eyes remained closed as he savored the warmth from the fire place, the rag, and Elaine.

The red head held a wrapped present in her hands, extended out towards Guybrush. “Go on, I promise you, it won’t bite.” She insisted.

Guybrush stared at the present hesitantly until she pushed it more forward, leaving him no choice but to take it. Unwrapping the present, he pushed the papers to the side and held his breath. Inside the wrapping was a familiar shade of blue he thought he’d never see again. He shakily ripped more of the paper until there was nothing left revealing a royal blue coat with red cuffs. His breathing was funny as he continued to hold the heavy coat.

“I-I don’t… I don’t understand…” Guybrush said quietly. 

“You don’t exactly have a coat, so I thought it would be wise to have something for the winter.” Elaine answered, hugging her knees. “If you don’t want it, I could return–”

“No.” He quickly cut her off as he brushed his thumb along the cloth and felt his throat going tight, turning to give Elaine a smile. “It’s… it’s fine. More then fine. I– thank you…”

She saw that small glimmer in his eye.

Guybrush didn’t want to go.

It took some convincing, but soon the three were in town watching the festivities, smelling the food, seeing the locals dancing around the bonfire, and sounds of laughter and songs lingering in the air. Winslow wondered off while Elaine went to grab a drink for both her and Guybrush, leaving the blond alone for a moment on that bench.

‘It’s just a festival.’ Guybrush mentally told himself. 

The shouts of the people screaming for grog, louder music– for justice and the lying Founders’ heads.

It’s just a festival.

The children running around the bonfire giggling and screaming– in terror as the guards started striking the colonists down one by one, their homes being burned to the ground.

It’s just a festival.

The metal mugs clanging into each other in drunken merriment– just before they hit the floor with the Founders gasping for air.

It’s just– I’m sorry.


A balloon popped and some kids screamed at the startled sound and his breathing sped up. Guybrush stumbled off the bench, disregarding his only support and hobbled from the bench, pushing past the people and towards an alleyway feeling sick. Everything was closing in on him, the smell of smoke, the sounds of screaming, he couldn’t breathe. His leg, screaming in agony, soon gave up causing the blond to fall to the floor hard, leaving him no choice but to push himself as far as he could in a corner and covering his ears as tightly as he could and his breathing too fast. 

‘I’m SORRY.’




He felt a soft hand on his shoulder and jumped, staring upwards at the redhead staring at him holding his cane and looking at him with concern. She didn’t need to ask if he was alright, it was apparent he wasn’t. Instead, feeling his eyes beginning to burn, his throat choking him, and his heart ready to beat out of his chest, he began to plea in a sobbing voice.

“I want to go home.”

“Libertalia?” He asked.

“Aye. A land free of the law, where men can be men and abide to no one but themselves. A safe haven for those who need a home and be as free as the wind.” Avery explained, drinking back from grog. 

“A place to call home…” Guybrush said quietly

“Think about it, in a hundred years, people will remember the name of the man who helped create the utopia of pirates. They will cheer and praise the name Guybrush Threepwood as the pirate who protected his kind.”

Guybrush gave a laugh, “Not sure if they’ll pronounce it right.” He looked at the floor with a finger on his chin. It was an interesting thought.

“So what say you, Founder Threepwood?”

The blond looked from the floor to the man in front, feeling his breath get stuck in his throat in horror as gibbets holding the colonists filled the room and the skeleton with flames in his eyes stared back with a devilish grin, holding the poison chalice that was filled to the brim spilling over and burning the table.

“For God and Liberty.”

Guybrush woke up screaming in sweat and tears.

“You shouldn’t blame yourself…”

“But it’s my fault. I should’ve known he wasn’t ready. I should’ve known it would overwhelm him.”

Winslow sighed as the red head sitting across from him had her hand on her forehead as if to hold her head up. All those months… all that recovery, out the window with just a single outing. He would be lying if he didn’t admit to feeling frustrated with himself.

“Being here is good for his safety and physical health, I know, but I don’t think it’s good for his mental well being. And each day I feel like he’s slipping further away and I’m just–” Elaine closed her eyes, she couldn’t bring herself to admit her fears. She remained silent, her eyes were beginning to burn with tears. “I’m scared.”

The portly man remained quiet, but understood her sentiments. “You’re entitled to feeling like that. It’s not easy trying to help lift a burden off of someone’s shoulders.” He spoke softly. “It’s exhausting. I’m just as guilty as to what happened back there, but it’s important to know that if you need someone to tag in while you rest or to talk to, I’ll happily assist a Threepwood.”

Elaine looked at him with bloodshot eyes. He just gave a small smile and a salute.

She gave a dry chuckle as she wiped her eyes.

There was a loud crash in the kitchen when Elaine ran in, spotting the various broken plates on the floor and the blond who seemed to have been dead center of it on all four while his cane was on the counter. She kneeled down and tried to help him when he cut through the sudden silence and spoke.

“What are we doing here.”

The red head had a hesitant look on her face. 

"What do you mean?”

“I mean… what are we doing here? W-we left this lifestyle to be pirates. To live out at sea. To be able to freely sail where ever the wind took us to our hearts’ content and now… now we’re stuck living in a tiny shack on some island instead of the Screaming Narwhal.”

Elaine remained quiet as she felt him shake. 

“I’m sick and tired of this place. I tried adjusting, I tried living with this cane, I tried accepting living by the shore. But I… I can’t do this. I can’t do this anymore.” Guybrush’s voice broke, tear drops hitting the wooden floor. “I know you and Winslow are doing so much and giving up a lot for my sake… I know. But I can’t keep lying to myself. I miss the sea. I miss feeling the breeze. I miss waking up to a new place. I miss our adventures out there. But instead, I’m stuck here with a busted leg, holding you and Winslow here, because I was too blind and too stupid and messed EVERYTHING up and I… I don’t know how much more of this I can take.”

She wanted to counter him. 

She wanted to tell him he was wrong. 

But all she could do was hold him as he cried his heart out.

Winslow finished cleaning the last of the new plates, placing them on the rack to dry. It’s been week since the Captain’s spill and his outcry… something that was going to haunt the portly First Mate for the remainder of his days. He knew the Captain was battered and bruised emotionally, physically, and mentally after the events of Libertalia… but he didn’t comprehend just HOW shatter the blond was. How does one come back after something like that?

Leaning against the counter and rubbing his face, Winslow let out a sigh. He usually had an answer for everything, whether it was regarding sailing, culture, intimacy… he always had an answer. But this time, he felt just as lost as the Threepwoods in this. 

Of course, he would never admit to either of the Threepwoods that from time to time, he would have nightmares himself or the fact that he would play ignorant regarding if he heard the Captain scream at night the following morning. The offer to leave would rise up every now and again by the Captain, and every time Winslow would decline the offer, saying that he’s been with him this long, he wasn’t going to leave.

Especially not after something like Libertalia.

He looked to his side where the Captain’s journal, which usually was always by the blond’s side, laid unattended do on the dining table. It hasn’t been touched in weeks. But then again, maybe actually vocally saying how he felt was needed. Winslow slowly glanced at the window facing the beach and spotted the blond sitting there, staring longingly at the waves as if waiting for something… for someone.

Perhaps the Captain’s old self again.

‘We’ll find him.’ Winslow thought to himself.

Winter came and left, leaving the warmth of Spring to thaw the chill. Elaine finished putting away the laundry and looked up at the shore where Guybrush usually sat, noticing the empty place in the sand. Strange, he was usually sitting there around this time. 

“Guybrush?” Elaine called out, looking along the shore for any signs of the blond when she spotted his boots, coat, and cane thrown on the shore. Her heart sank. 

He wouldn’t.


He wouldn’t!


She looked at the ocean, feeling her breathing sped up as tears started to spill. 


As if compelled by an outside force, she rushed into the water, calling out her husband’s name frantically. 

This isn’t happening… this isn’t happening…!!

A splash broke the water’s surface as someone gasped for air. Elaine turned to look and spotted the blond in the water swimming back to shore, blissfully ignorant before he turned and looked at her confused.


Her breath hitched. She rushed further into the water, tackling Guybrush back into the ocean, hearing an ‘oof’ from the blond as he landed hard back down and her arms wrapped tightly around him, shaking. She forgot that he could hold his breath. How stupid could she be? Of course he can. He always could. He wouldn’t dare–

“Elaine I– are you okay?”

“Promise me you won’t give up.”

“Promise? I don’t–” 

“Promise me!”

He held her tight as he heard her begin to sob. He never meant to scare her, but he could only imagine what it must’ve looked like just now to the red head. Guybrush held Elaine and brushed back some of her wet hair.

“…I promise.”

“And I’m telling you, it wasn’t THAT bad. A good coat, pants, and boots and you’re fine.” Elaine argued.

“I have seen my fair share of winters, and THAT was just nipping at my nether regions.” Winslow countered.

“You’re exaggerating at this point. This Winter was chilly and yes… things tended to stick together but–”

"I swear, it stuck the two gents in my trousers together!! TO MY TROUSERS–!!”

A snort sound cut into their conversation.

Freezing in place and turning around to the source, they spotted the blond sitting and covering his mouth to try and hide the chuckle. The two briefly looked at each other, wondering if the other heard that laugh before looking back at the blond who was struggling more and more to cover his giggling fit imagining the portly man waddling around before breaking out into more laughter.

“H-how does that even work?” Guybrush asked between laughs, “You had to have looked like a penguin! Ha ha ha ha!!”

Elaine and Winslow sat and watched the blond laugh– GENUINELY laugh. Something they both could’ve sworn they would never hear again. Winslow side-eyed Elaine and saw her tearing up but with a smile on her face. ‘There he is. There’s Guybrush Threepwood.’ Winslow thought to himself, feeling just about ready to cry himself. Instead, he cleared his throat and continued.

“Simple, Sir. You see when one of the nuts–”

“WINSLOW!!” Elaine whipped her head in shock but was nonetheless laughing, Guybrush laughed even harder to the point that he fell over. They both knew that there were still a very long and winding way until Guybrush recovered, but they savored the moment and laughed along with him.

It was good to hear him laugh again.

Chapter Text

He pulled the wagon behind him filled with groceries and other miscellaneous items Elaine asked for in town, limping on his crudely taped together cane from town back to the small place he called home… reluctantly. Placing a hand on the knob, he opened the door only to be greeted to a very vibrant, balloon and streamer filled living room with Winslow and Elaine standing there wearing hats and yelling loudly “SURPRISE!!”

Feeling his heart stop and his body going numb, Guybrush let out a yell as he stumbled backwards and fell flat on his back, causing the wagon to tip over as the blond groaned in pain. The two rushed over and quickly kneeled down worriedly, “Guybrush, are you alright?!” Elaine asked.

“Uuuugh… y-y-yeah… peachy.” Guybrush groaned as he rubbed his lower back, he looked around the room as he tried to slow down his heartbeat. “W-what’s going on?”

Elaine frowned as Winslow took off the party hat and looked at Guybrush with concern “It’s your birthday, Sir…”

“My… that’s today?” Guybrush asked as Elaine and Winslow helped him stand up.

“Of course it is. Much like how it was last–” Elaine stopped herself and pressed her lips. Right… 

“Guybrush please.” Elaine chased after Guybrush down their mansion. How odd that the tables have turned that now she was the one chasing after him from going to those meetings. “Just five minutes. I’m sure Avery and the others can wait five minutes.” 

“Elaine, I can’t. Last time I was late by two minutes, I got an earful from Tew. I… I really have to go.” Guybrush frowned as he began to head towards the door. “Whatever it is, I’m sure it can wait. I… we can talk about it when I come back, promise!” 

When the door closed, Elaine clenched her fists angrily before sighing and letting her shoulders sag. It wasn’t unusual that he would forget… but it’s been far too long since she could recall them celebrating the blond’s birthday. She would’ve wondered if the Founders would recall, but they barely remembered his name.

By the time Guybrush returned, it was already long past midnight and past his birthday as Elaine remained fast asleep… he didn’t even remember asking her about what it was she was chasing him about and didn’t feel the need to ask the following morning.

With one hand on his back and the other hold in hand, Elaine guided him to the kitchen while the blond kept his eyes closed. “Okay… now you can open it!” She said happily. Guybrush blinked his eyes into focus and stared at the table where a clearly home-baked cake sat with a very loose (sloppy, really) ‘Happy Birthday Guybrush!’ scrawled on it.

“Happy birthday, Captain.” Winslow said quietly with a soft smile as he shook out the match that lit the candles in the dessert.

“Make a wish, love.” 

Tap. Tap.

The two looked over at Guybrush who was silently crying as he continued to look at the cake. His breathing hitched, Guybrush tried rubbing away any tears with one of his hands but felt like it was doing nothing as he continued to cry. For the life of him, he couldn’t recall a single moment he celebrated his birthday in Libertalia… even wondering so far if he even deserved it. Elaine wrapped her arms around him and held him tight as Winslow walked over and joined in on the hug.

He tried saying thank you… anything at all to indicate to the others how appreciative he was of it, and yet nothing came out save for a few gasps and sniffing. But in that moment, he was glad to be in the arms of the people he cared for most and it was apparent to them all that this birthday meant more then the others in the past. 

And they were going to be sure to celebrate it.

Chapter Text

Guybrush hobbled in town one early Spring morning with a cane in one hand and a bag of food in the other. While he normally did enjoy to just sit by the shore and attempt to put his feet in the water, he figured it would be nice if he treated Elaine and Winslow with a surprise breakfast, and in truth, he felt like walking. Taking in a deep breath, the blond savored the tranquil town, seeing the stores slowly open and the quiet murmurs and–


He stopped in place and turned his head towards the source of the sound and walked over to the alleyway, looking around for the source when the whimpering got loud and louder and the closer he go. “Where…?” He muttered and looked down when he spotted what looked like a ball of fur no bigger then the his hands curled up deep in a box and shaking. Guybrush carefully kneeled down and placed his cane and bag of food to the floor so he could be at eye level with the small thing before he let out a gasp.

It was a small puppy.

He strolled through Libertalia one day in as he was making his way towards another meeting with the Founders, seeing the bumbling life of the ever growing utopia and his chest being filled with pride and joy. Guybrush would give a wave and smile to those who said hello or greeted him with a good morning as he continued to make his way when he heard a small bark. Odd, who would be barking? Guybrush looked at the sky, figuring he had some time to spare and decided to follow the source of the sound, finding a small dog barking and whimpering at a pie on the window sill. The blond frowned, seeing the small puppy looking hungry and walked over, peaking his head over the window and noted the baker being busy before smirking and grabbing a piece of the crust before ducking back down, more of a force of habit rather then the fear of being caught. He was a Founder, he could get away with. “Here you go, little guy.” The blond smiled, handing the crust to the puppy who happily (and greedily) grabbed the crust and devoured it. Guybrush let out a laugh as he began to pet the dog’s head and it licked his hand, expecting more food. “Who’s a good boy? You’re a good boy!” He cooed when he heard someone clear their throat. Looking up, he spotted Founder Bonnie with her hands on her hips and her foot tapping. 

“Pleased with yourself?” She asked.

“Ah… yes. Yes I am.” Guybrush retorted.

Bonnie rolled her eyes before poking at her wrist as if to indicate the time. “C’mon, we have to get going.”

“But–” Guybrush looked down and saw the dog whimpering, feeling his heart break. He gave the dog another scratch before standing up. “Sorry, little guy…” 

“Hey, little guy…” Guybrush spoke softly to the little puppy, who opened it’s eyes slowly to look at the blond. “It’s alright, I’m not gonna hurt you…”

Carefully, he extended his hand out for the dog to sniff, which it did but it let out a whimper and lowered it’s head. Guybrush frowned and retracted his hand. “What’s wrong, little guy? Not feeling well?”

The dog gave a huff and a whimper.

He bit his lip trying to think what he could do and sat up, digging into the bag of food trying to find anything to feed the dog and ripped a warm piece of bread. Lowering himself once more, he carefully placed the bread in front of the puppy who sniffed it cautiously before licking and eventually eating the bread. Guybrush smiled and extended his hand out once more to pet the puppy. 

“Atta boy…” Guybrush cooed. The puppy sniffed his hand once more and gave it a lick, as if expecting more food before lowering it’s head once more, causing the blond to sigh. “Can’t leave you here… hmm…”

Guybrush looked around, wondering if the owner was going to show up. After several minutes of nothing and the puppy’s whimpering not going away, Guybrush let out another sigh and rubbed the back of his neck. Ripping another piece of bread, Guybrush laid it out in a way to get the small dog out of the box, and needless to say it worked but couldn’t help but frown as the dog barely wobbled over to the food. Carefully, Guybrush lifted the puppy as it finished up the second piece of bread, feeling his heart break as the puppy barely weighed a thing and soon the bag of food before gripping his cane and slowly standing up. 

“C’mon… let’s get you taken care of.” Guybrush smiled softly, the whimpering slowly subsiding as he felt the puppy licking his hand and causing the blond to chuckle as he began to hobble his way back to the shack.

Chapter Text

There was no denying that since the small pup that he had named Captain Savage (Or C.S for short), it helped the three of them for the better as it acted as a small alert for Guybrush. And surprisingly, it didn’t take much to convince Elaine to let him keep the dog. More-so since no one put a claim of a missing dog. 

He strolled through town with C.S by his side one cloudy day after yet another doctor’s check up. The news were as grim as they always were and the cane continued to mock him relentlessly, but the outing was admittedly needed… even if he was tempted to whack said doctor with said cane. He didn’t pay much mind until there was a sound of wood smacking against wood and a voice that sent a chill down to his core.

“Avast ye bleeding heart! I be pilligin’ yer gold!!” A young boy shouted as another group started cheering and shouting. 

“For God and Liberty!” Avery shouted as the Founders raised their glasses.

The cane dropped to the floor and Guybrush stood there with a vacant expression on his face, his breathing becoming erratic. “No… no no…” Guybrush muttered, gripping his head as Libertalia flooded his view. The fire, the screams, the poison… Avery’s sick grin marching closer and closer and the shouts becoming louder and louder. “I’m sorry… I’m sorry…” 

He stood in the center of the street, unaware of the carriage charging it’s way towards him when he faintly heard the sound of barking and felt a tug at his pant leg causing him to stumble backwards against a building’s wall and away from the busy streets filled with horse carriages that snapped his cane in half. Hesitantly turning his head, Guybrush looked and saw the patch-eye wearing dog barking and clawing at his arm trying to grab his attention. Libertalia slowly disappearing and the town reappearing… but C.S remained consistent and barking, nudging itself into him to get Guybrush to pet it’s head. He weakly lifted his hand and began petting the dog, and with each stroke, the dystopian island slowly but surely vanished.

Guybrush dropped his hand from the pup’s head and started holding his head, shaking. He didn’t know how long he was in that position when there was a nudge of a small paw against his thigh causing the blond to look up and see C.S wagging it’s tail. He gave a weak smile and rubbed his eyes, leaving himself open for C.S to climb up on his lap and rest it’s two front paws on his chest and licking his chin. Guybrush shook and held C.S tightly, letting his anxiety course through before composing himself. “Thanks, Captain…” Guybrush said with a raspy voice. He stared at the destroyed cane and the smile dropped. He hated the damn thing, but he was pretty much useless on land without it.

The pup let out a bark before hopping off his lap and running off, leaving Guybrush to sit by the building and waiting… it was all he could do. A half hour passed before he heard the sounds of Captain Savage barking towards him, stopping only in front before turning around and barking some more. Looking up, he saw Winslow running afterward. ‘Smart dog.’ Guybrush thought.

“There you are, sir!” Winslow panted. “We wondered what happened when Captain Savage came running and barking.” Guybrush shrugged and pointed at his destroyed cane. Winslow looked over and sighed. “I see… very well.” He walked over and helped Guybrush stand up, an arm around his waist allowing the blond to lean his weight on the portly man as the two began to make their way back to the shack, with Captain Savage walking alongside with the top half of the cane in it’s mouth. Winslow gave the blond a smirk as he noticed his eyes were on the dog and smiling. 

“Good dog.” Guybrush smiled.