Bard awoke one morning to the insistent tapping of a child at his window. He opened the window. “Letter for you, Mr. Bard!” Still half-awake, he took the envelope, put it on his nightstand, and went back to bed.
After breakfast, he opened it.
To Bard, of Lake Town,
A matter has arisen which desires your involvement. Namely, your assistance is required in dispatching the Dragon, who once slept in the Lonely Mountain but is now awakening.
Three days from now, please present yourself at the front gate of the Lonely Mountain with yourself, your bow, and your Black Arrow. You will be met by an accomplice who will assist you in this task.
Your discretion in this matter is appreciated; Lickspittle’s spies are everywhere. If you ask me about this letter, I shall deny it and have you thrown out of town.
And so Bard made some preparations, and three days later he was at the gate of Erebor. A rumbling came deep from within the mountain, and a creaking, and a grinding of chains. Slowly, achingly, the gate ground upwards. Fifty feet above the pavers, it stopped rising.
Bard saw no sign of the promised accomplice.
Some more thumping and banging came from within the mountain. A wheel-shaped chandelier the size of Bard’s house rolled out from the depths of the gate, crossed the courtyard, and made an attempt at crossing the bridge over the River Running before finally falling over.
“Drat.” The voice that boomed in the deep was definitely not human.
Well, if his accomplice was to be a troll, it would be better to know sooner rather than later. Standing up from behind his rock, Bard yelled, “Hello!”
More metallic crashing inside the Mountain. Then came a slithering, and finally a monstrous head emerged from under the gate. Glistening red, coated with dust, a thousand scales glittered in the partly-cloudy midday sun.
“Good morning! A mister Bard, I presume? I’m sorry that you’re seeing the Mountain in such a mess as this; I didn’t think you’d arrive until this afternoon.” The fearsome head turned both eyes, both nostrils, all of its teeth upon him. Bard quailed in his boots, just a little.
And then he climbed on his rock, and unshouldered his bow. “I am Bard, last of the line of the kings of Dale.”
“Oh, good, I was hoping I remembered your name correctly. Do come in; it’ll start raining in an hour and I wouldn’t want you to catch a cold.” Smaug closed its fang-filled mouth for a moment. “Don’t worry, little human. I won’t harm you, and you can still harm me with your Black Arrow. Would you like some tea? Rhûn sells some excellent blends.” And with that, the fearsome beast’s head disappeared into the dark hall.
The slithering of the withdrawing wyrm paused again. In an over-the-shoulder sort of way, Smaug said,“Oh, and if you don’t come, I shall be quite disappointed.”
Figuring himself quite stuck in the predicament, Bard clambered down to the courtyard. He walked under the gate, which was ten feet thick if it was an inch. A miracle of Dwarven engineering, and all he could think about was what if it were to fall.
The main hall was as wide as the pool in the middle of Lake Town, the ceiling impossibly high up in the darkness. At the far end was a huge arch, standing fully as tall as the Master’s Great House in Lake Town. The arch opened onto a T-shaped passage, lit from the left by a light that sparkled and glowed. With no sign of the dragon; Bard walked towards the light.
It was a really long hall.
A few hundred feet from the end, he heard the Dragon’s voice coming from a side passage. “You can go through the big door, but there’s a chair in this room sized for you, and I can pour you tea here.” The door the voice came from was open, and also lit with that same shifting golden light. Just less of it.
He walked into the room, which despite being in a Dwarven city was appointed with furniture sized for Men. There was a Man-sized armchair, a settee, a table with a tea set, some bookshelves, and a small fireplace. Where one would normally place a lamp on a hook in the ceiling, there was instead a contraption of rods and pulleys that speared down towards the table, ending in a pair of leather gloves. The contraption shifted with purpose; the gloves were making a pot of tea. And over all of this played that golden light.
The wall he had just walked through had a door. The wall to his left had a bookshelf. The wall ahead of him had a fireplace, burning merrily. And the remaining wall was no wall at all, just a broken hole in the mountain, opening on the a cavern filled with gold and gems and motes of dust floating in the air.
Atop the pile was the dragon; its huge foreclaws tangled in — no, pulling on a number of iron hoops. The hoops hung from the ceiling by fat ropes, which looped across the ceiling on pulleys to massive arrays of springs, and then ran as narrower ropes to smaller springs, and thence to the cables that disappeared in the wall above this room. Smaug’s claws wriggled in the hoops; the arms hanging from the ceiling extended a cup of tea and a saucer towards Bard.
Bard did the only thing that made sense to do, and took the teacup.
The dragon withdrew its claws from the rings, and turned to face the man. “I must admit, I have misplaced my Rhûnish tea. This mix is called Daughter of Fishes, and comes from a very, very far-off land. Please, have a seat.”
Bard took a sip. It was adequate tea. He sat.
“I should introduce myself,” said Smaug, destroyer of Dale. “I am Smaug, fire-drake, chiefest and greatest of calamities. You, I hope, are Bard, captain of the guard of Lake Town, and direct descendant of Girion, Lord of Dale. Did my letter reach you alright?”
“Oh, good. I was worried that the shepherd would pocket the gold he found with his sheep and not pass on the letter. But, to business. I wish your help, mister Bard, in deceiving the world. In seven days’ time, a band of dwarves will arrive in Lake Town. The Master will feast them and send them up the river, hoping that the prophecies will come true. How does the song go? ’His halls shall echo golden to songs of yore re-sung. The woods shall wave on mountains and grass beneath the sun; His wealth shall flow in fountains and the rivers golden run,’ or words to that effect.
"These dwarves and their burglar shall oust me from their home, and I shall fly in fire and fury to Lake Town and make to attack it. This is the point where you come in. Would you like a biscuit?”
The first attempt did not work, of course. Bard shot Smaug with the Black Arrow and ended the Loop.
It was twelve Loop restarts before Smaug was able to get the conditions right to make Bard amenable to Smaug’s offer. (Really, the number had been more than a thousand, but Smaug was only counting the Loops with the same mix of loopers.)
That night, when Smaug flew over Lake Town, glittering in the torchlight, the Thrush that landed on Bard’s shoulder expressed surprise and alarm. “Wait! Wait!” it said to him. “The moon is rising. Look for the hollow of the left breast as he flies and turns above you!” And while Bard paused in wonder at the talking bird, it told him of things that Smaug had predicted would occur.
As the fearsome beast breathed flame into the air over the town, setting the tower of the Great house aflame, Bard saw a painted circle on the dragon’s breast, like that on an archery butt. It was not over the hollow of the left breast, but on the hollow of the right breast. Remembering his promise to the dragon, he drew and fired, while the Thrush sqawked indignation.
Smaug screamed, long and ear-shattering. Its flaming stopped; its wing-beats stopped just as he flew over the Master’s barge. With a crunch and a splash, the calamity fell into the Lake. There was a great hiss as the Lake flashed to steam, and a fog sprang up immediately.
Bard shrugged, and went to see to the evacuation efforts that were ongoing. Smaugh had not targeted Lake Town proper, but a number of houses were accidentally on fire, and the Great House’s fire was in danger of spreading.
Under the Lake, Smaug gloated, holding his breath. And then he stepped between, and disappeared to a land far in the cold North of Arda. He had spent twelve loops trying to get the setup right. And now that Lake Town believed him dead, the rumor mill would fly as usual. Olorin would not be expecting Smaug’s appearance anywhere in Arda.
Smaug had spent a long time thinking about what to do with a Looping Gandalf, unaware of a Looping Smaug. Showing up at the White Council meeting in Rivendell had been done before. He’d been an accountant in the Shire. He’d taken out Barad-Dûr ahead of schedule. He’d flown with the Eagles of Manwë. He had deposed both Saruman and Denethor, and once ruled the corsair fleets of Umbar.
This time, Smaug was going to start a business. He’d need to drive some technological advancements, but snowshoes weren’t terribly out of canon. Architecture would be a problem, but the Looping dragon already had blueprints and snow maps, from that one Loop where the Valinorean Winter Games were held in Rivendell. All the downhill events had been in the Misty Mountains. Smaug knew the slopes, the snowpacks, and indeed he knew where he could find several million board feet of lumber. He would have to hire some blacksmiths and carpenters, of course, but as long as he hired only from the settlements of Men on the eastern side of the Misty Mountains, and primarily worked through proxies, he would be able to pull it off.
And as for out-of-Loop techniques, he supposed that the worst he’d need to do would be to use shadow clones for snow-clearing operations once the snow sheds and avalanche galleries were built. Maybe some dynamite, if he wasn’t going to hire Dwarves for tunneling. He could run this operation as close to baseline as possible, and as long as Smaug kept the operation small and quiet, Gandalf would have no inkling of it coming.
Smaug was going to make a toll road over Caradhras.