First Era Whiterun, in its heyday, was a quiet little town. Built up by Jeek of the River in the Merethic Era to surround Jorrvaskr, Mead Hall of Ysgramor and his Five Hundred Companions, Whiterun started off as a simple Nordic village; generally devoid of aesthetic pleasures and solely created for functionality. Whiterun was renowned for having the finest steel in all of Tamriel, thanks to its strategic location surrounding Skyforge, the ancient forge discovered by the Atmoran travelers. Houses, farms, and mills began popping up around the area, and the wall and castle known as Dragonsreach soon graced the now bustling city.
In the Fourth Era, Whiterun had lost much of its fame and admiration; the city had suffered greatly from several plaguing factors. Frost troll populations began to rise, and the attacks would frighten curious travelers away. The harsh winters would occasionally freeze crops, forcing a cluster of citizens to relocate south to Riften and Falkreath. Bandits had become more prevalent in the hold, often setting up camps or residing in old, abandoned fortresses, lecherously gazing upon the city due to its wealth. The biggest problem that had diminished the once-grand city of Whiterun was the Civil War. Whiterun was the sole neutral city, and given its location at the center of Skyrim, was coveted by both the Imperials and Stormcloaks alike. Many civilians packed up and migrated elsewhere out of fear that there would be battles and aggressive invasion for the city's alliance.
As the Civil War raged on, people died. Stormcloaks, Imperials, even innocent civilians who had been caught up in the inevitable crossfire. Some were mistaken as bandits and killed on the spot, others had died of the famine caused by the frostbitten crops, and others still continued to die of natural causes.
Brynjolf's parents had passed on at around the same time. First, his father had been killed by a frost troll while hunting for food, and a week later, his mother died in the care of the town's healer after suffering from malnutrition. Brynjolf was angry about his parents' demise. He was angry that there was nothing he could do.
An unsettling thought had soon planted seeds of doubt in his mind, however. Without his parents, how could the teenaged Brynjolf support himself? No one in Whiterun would be willing to take in a fourteen year-old as their adopted child, and it was highly unlikely anyone would care to employ one, either. The young auburn sought out life as a humble fisherman, but upon realization, he remembered how stealthy and quiet he was whenever he snuck out of the house at night.
Months of petty thievery ensued. First it was little baubles and trinkets, stuff like loose change and the occasional silver ring. He would sometimes come across food, and whenever he was lucky enough to swipe an apple or a carrot, he would save his stolen merchandise to sell on a rainy day and enjoy his meager rations.
One fateful morning, Brynjolf approached the market stalls in the Plains District. He stole a glance over at one of the hastily-crafted stalls where Yvrilde Valentia and her daughter, Carlotta, peddled produce. Brynjolf took note of the two young women and casually walked up the steps to the Wind District before cautiously lurking at the top, waiting for an opportune time to swoop in like a vulture and pick someone's pocket. The orange-haired woman turned to her daughter, looking down at her with a warm smile. "We'll be eating at the tavern tonight, dear. Get your nice dress and good shoes when we close up today."
The little girl looked like she was about to burst with joy. "YAY! Thanks, mom!" Carlotta chirped, excitedly clapping. "When I grow up, I'm going to run the market stall just like you, and my daughter will, too! Oh, and her daughter, and her daughter..." the eager child continued. "...and her daughter, too!" Carlotta exclaimed, giving a little jump of excitement.
Unfortunately for her, Carlotta's arms had knocked over a flower basket that sat on the stall. Flowers burst out of the little basket, and Carlotta gasped, quickly beginning to pick up all the flowers she had dropped. Yvrilde giggled at her daughter and bent over to assist her, and Brynjolf saw his opportunity. He quickly descended the steps and innocently strode over to the stall, dipping his hand into the pocket of her dress, and stealthily removed what felt like a necklace. He palmed it in his hand and slipped it into his satchel, strolling to the secluded area behind the Bannered Mare. Brynjolf quickly pulled out the necklace without even checking his surroundings and self-appraised it.
The glittering gemstone in the center was, to his knowledge, a flawless diamond. "Hot damn!" Brynjolf almost shouted, trying not to laugh out loud. "It's a miracle." He whispered to himself, clutching the piece of jewelry to his heart. His skin went cold when he felt the hand of a stranger on his right shoulder. "I saw what you did back there, young man." The stranger began, and Brynjolf felt all the blood drain from his face. "And I must say, I'm indubitably impressed." He praised, giving a few claps of approval. Brynjolf slowly turned around to see a middle-aged Imperial dressed in a cloak and hood. He could scarcely see the man's face, but he noticed his mid-length raven locks. Brynjolf gave a skeptical scoff. "Is this some kind of joke?"
The man chuckled heartily and shook his head, putting a surprisingly reassuring hand upon the young lad's shoulder. "No, no. Certainly not. This is a business proposition." He explained with a smile, and though Brynjolf could not see the man's eyes, he knew they were gleaming with excitement. "A business proposition? Who are you?" Brynjolf suspiciously questioned. "Ah, who am I? Well, if it helps you feel more at ease, I'm someone who's not looking to turn you in to the guards. No, it's the exact opposite, you see." He gave a nod of approval as he saw Brynjolf relax a bit. "My organization is always on the lookout for talented young lads such as yourself. If you want to make good use of your recherché skills, you should come to Riften and join up with us if you're interested."
Brynjolf watched as the man suddenly snatched the flawless diamond necklace from his palm, and in its place sat a thick coinpurse. The seams of the fabric were about to come undone due to the amount of coins it contained, and Brynjolf had to hold the purse with two hands to keep himself from dropping it. "How many Septims are in here, sir?" Brynjolf asked, astonished. "To be approximate, around four thousand." "Four thousand?!" Brynjolf gasped, his jaw agape and his emerald eyes wide with shock. If Brynjolf wasn't intrigued by this man previously, he certainly was, now.
Hours later, Brynjolf found himself bouncing up and down as the carriage he and the man had rented pulled them forth. "When we get to Riften, I'd like you to complete a special task for me. Think of it as your initiation." The man explained. "Alright, what do I do?" Brynjolf queried. "At nightfall, head up to Mistveil Keep, the castle of Riften. By the Jarl's bedside, there's a copper and ruby circlet with a serpentine engraving. Fetch the circlet and bring it to the Ragged Flagon in the Ratway." The man paused, and a look akin to worry crossed his face for a split second before it returned to his normal expression. "Kid, I like you, so I'm going to give you some advice. The Ratway isn't exactly a kid-friendly area. Hell, it's not an adult-friendly area, either. Just watch your back, keep low, keep quiet, and if you manage to contract Ataxia from any of the skeevers down there, go get it checked out at Elgrim's Elixirs." He advised, turning his head towards the city walls as the carriage slowly came to a stop.
Brynjolf gathered his backpack and satchel and turned to the man, who was about to leap off the carriage. "You never told me your name, sir." Brynjolf mentioned. "Oh, how rude of me," The man replied, hopping off the carriage. He landed perfectly on his feet with a thud, and he glanced back over his shoulder at the auburn teenager. "My name is Gallus Desidenius, your Guildmaster."
A/N: Thank you for reading this one-shot. Be sure to check out my other Skyrim stories Where The Cold Awaits and Shambles Of A Dying World. I advise you to read Where The Cold Awaits first, though, since the second story is a sequel to it.