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Winona Kirk loves her son. She has loved him from the moment she knew that he existed. Love isn’t everything though, because despite this love Winona has always had a very complicated relationship with her youngest son and now, unfortunately, only living child.

Battling postpartum depression exacerbated by watching the love of her life die in a blaze of glory did not exactly make her mother of the year material. Jim’s early years were not the best for anyone involved. She’s not going to lie and say that she wasn’t resentful. However, it wasn’t Jim who she was mad at but George which would be hard for small child to grasp.

Sam didn’t make things better. When he was seven, the boy asked if they dropped off Jim off at an “orphanage” would he get his dad back. This just happened to be during Jim’s third birthday party. They started celebrating Jim’s birthday on January 5th after that incident.

In hindsight, she should’ve put all of them into therapy afterwards, but she didn’t. She didn’t realize there was a problem. She didn’t realize that she wasn’t being the mom she needed to be to both of her children. She was lost in her grief and the only time she felt okay was when she was working. This meant leaving her kids behind with who she now regards as the world’s worst rebound relationship ever.

Winona had many regrets on how she handled life post George; her biggest one was not finding herself on Dr. Suarez’s couch until Jim was old enough to drive. If she had gotten help earlier, then maybe she would’ve avoided her abusive second husband like the plague and Sam wouldn’t have run away at 14. Also, Jim would not have asked to be emancipated at 15, because he didn’t want to go with her back to Frank. Even then, Jim saw things more clearly than she did.

That was her rock-bottom that made her get help. She reevaluated a lot of life choices and ended up going back to school to retrain as a counselor/psychologist (after leaving Frank for good). She wanted to help other people avoid her screw ups. While she was helping other people, her sons were drowning and Sam’s case quite literally. At the age of 25, Sam’s body was found in the bottom of his apartment complex pool. The cause of death was listed as drowning, aided by intoxication. She never read the coroner’s toxicology report regarding Sam. She never would. She’s just thankful that Sam’s ex-girlfriend, Arlene, was the one that called her.

As bad as losing Sam was, it brought Jim back into her life. No one wants to see their child for the first time in six years at the funeral for their other child who they hadn’t even seen for even longer. But that’s what happened. Jim was angry, at her, at the world, but mostly at Sam, especially when he found out Arlene was pregnant with a daughter that Sam would never meet. It felt too much like history was repeating itself.

She was shocked that he hugged her. Winona was even more shocked that he took her communicator number and said he would call her. She didn’t expect for him to actually call her. Except he did, a week before his birthday and three days after Samantha Kirk was born. Unfortunately, the Riverside Correctional Center logo in the back told her why he was calling.

"Let me guess, you’re calling because I’m probably the only one you know that would come get you out of jail at 4 AM." She had really been hoping he was calling to ask about Samantha not something like this.

“Well, you’re the only one I know that could afford it.” Jim joked. She hoped it was a joke anyway.

"Just because I can doesn’t mean I should. Why are you in jail right now?" Winona asked rubbing her temple.

“Nothing big. There may have been a little bar fight.” She doubted it was little, considering the large bruise that covered Jim’s eyes.

“You’re almost 22 and an uncle. You shouldn’t be getting into bar fights.” She lamented. Yes, she realized she probably shouldn’t have said that, but it was too early for her to think coherently.

“I was working and big burly biker dude decided he did not like getting cut off. There went half the bar and I’m probably going to have to get a different job."

"Jim, you’re better than this.” She stated trying to keep her voice neutral.

 

“Now you try to be a mom.” Jim scoffed.

 

“Okay, I deserve that. I wasn’t back then and it took me a while to realize that, but I got help. You are a god damn genius, who shouldn’t be calling his mom to get him out of jail due to things going bad at his dead-end job. You were done with high school at 16 despite your year off.”

 

“Year off? Is that what we’re calling the Tarsus fiasco?” Jim interrupted. Winona continued not wanting to think about Tarsus.

 

“You were valedictorian and had an acceptance letter to..." Winona started to say, but she’s cut off.

 

“I graduated early because I hated everybody talking about my dead daddy and my time on the colony of the damned. I wanted to be out of there as soon as possible, but you didn’t see that at the time because you were too busy crawling back to your bastard ex-husband. How’s Frank? I didn’t see him at the funeral."

 

“I have no idea. Frank has been out of my life since about three months after you left. I haven’t seen him since I signed the papers and I have no plans to.” For half a second she saw Jim’s smile before he became completely serious again.

 

“Nice to know you made some positive changes in your life. So are you coming to get me out or am I going to find out what the Riverside Correctional Center serves for breakfast? I’m hoping for Froot Loops." Jim joked.

 

"I should let you check out the haute cuisine of the Riverside Correctional Center, but I’m not.” ‘Because I feel guilty for my many shortcomings during your childhood’ remains unsaid, but is understood by both of them.

 

She did get Jim out of jail that night and dropped him off at his way too tiny apartment in time for him to feed the stray cat that she’s sure Jim accidentally adopted. Jim named her Lucky, so obviously she was his. This scene was repeated three more times over the next five months. Not every occurrence involved bar fights. There was at least one incident of Jim being picked up on allegedly breaking into the servers of the George Kirk Memorial Archives in London. Yet, she kept going to pick Jim up because at least he was still reaching out to her. Sam had never done that.

 

It was at this point that Winona realized that she couldn’t deal with Jim alone and called Chris. Captain Christopher Pike was probably one of the few people in Starfleet that she still talked to. Jane Barnett was the other one, but she doesn’t count because Winona new her long before her husband convinced her to be the Starfleet spokesperson. It’s funny that she met both in a similar fashion. She met Chris while he was doing interviews for his dissertation on the Kelvin incident and Jane while she was conducting interviews to do a documentary on the Kelvin incident. However, it was Chris whom she needed right now.

 

"I need help." Winona said as soon as Chris popped up on the viewer, shirtless actually.

 

"I assumed that you did considering your calling me at 4 AM San Francisco time." Chris said with a sleepy smile.

 

"I forgot about the time difference. Sorry.” Winona apologized with a slight grimace. “I just got a phone call from Jim asking me to go bail him out of jail again."

 

"I doubt your calling for bail money.” Chris joked. “I heard you’re doing quite well for yourself in your new practice."

 

“It’s the fourth time I’ve had to get him out of jail since Samantha was born. Jim is brilliant, but he keeps doing dumb stuff like getting arrested for bar fights or hacking Starfleet servers. Thankfully, the charges keep getting dropped, but eventually he’s going to run out of luck. I don’t want him to end up like…” Winona couldn’t even bring herself to say Sam.

 

He was her greatest failure. If she had left Frank earlier, he would never have run away. If Sam hadn’t run away, he would have never got into hard drugs and she would not have had to bury him before his 26th birthday. She felt like Jim was also going down a bad road, not the same one as Sam, but not a very good one all the same. She wasn’t going to let that happen a second time. She felt like Chris could help her.

 

"Jim needs structure or at least some sort of goal to actually strive for. I think you can give him that." Winona confessed.

 

"The only structure I can give him is in the form of getting him into the Academy. I’m not sure that you really want your son in a Starfleet uniform. After everything you went through with this organization, I doubt you want that. Hell, your last assignment was Tarsus." She closed her eyes, not wanting to remember.

 

“He’s always wanted to prove that he could be better than George. I’d rather have a Starfleet Lieutenant as a son then deal with the Sam situation again. The more good people in Starfleet, the less likely cluster fucks like Tarsus will ever happen again. Besides, I know that you’ll watch after him."

 

“Like he was my own" Chris reassures her.

 

“I just can’t have Jim end up the same way. I already have one grandkid being raised without a father."

 

“It’s not the same.”

 

“I know, but that doesn’t mean I don’t need your help.”

 

“And you know you always have it. So you want me to meet him?" Chris asked.

 

"Next Friday night you’re in town corralling rowdy freshmen at the bar across from the Shipyard, because we both know you will be, just point out to Jim that he can do better." Winona suggested.

 

"You’re sure he will be there?" Chris raised an eyebrow at her.

 

"Yes."

 

“Fine, I will talk to him, but I make no promises. I’m sure he’s just as stubborn as you.”

 

"Worse, really." Winona smirked at him.

 

“If this works, you owe me dinner at the best steakhouse in Iowa City.” Chris said as he ended the call.

 

Two weeks later she was absolutely ecstatic when Jim called to let her know he was joining Starfleet Academy and would she mind keeping an eye on Lucky. She could rest easily at night with a small furball sleeping next to her now that Jim was on a different path. However, it would be years before she realized what or rather who that path would lead to.