Brynjolf is, and always has been, an opportunistic, optimistic, and odd character. He’s had a penchant for charlatan business since he could hear and understand those darling fables of gold. Although his mother gave a valiant attempt to curb her only son’s eagerness for trouble, he ultimately embraced his “line of work” very young. Thankfully, the good citizens of Riften were spared his mischief for many years; both Brynjolf and his mother lived in a shambling hovel far in the woods. They were located in the Rift, but the shack he’d called home did not neighbor the city walls. Immersed in poverty with no foreseeable break from it, he fell in love with the concept wealth from one of the many books his mother had scavenged. Unable to hold a job, she performed simple chores, odd tasks, occasional prostitution, and acted as a meager trader for what little funds were offered by brief employers.
When she passed away due to Syphilis, Brynjolf was left on his own. He was the lone figure who buried his mother with a few, favored possessions. Fearing infection himself, Brynjolf hastily took to traveling after it. He dropped by a passing farmhold, where he stole away eggs and milk in desperation, but was promptly chased off by a very upset wife who’d mistaken the starving child for a creature of the wilds. He did not thrive while on the roads. Being scarcely above the age of twelve, he was a poor hunter (at best) and lacked a certain faith in his human brethren. With little food, he was gaunt in figure and his complexion was rarely free of muck. He slept in barns, sheds, abandoned homes, and empty camps until he staggered into Ivarstead. He snatched whatever food items were either discarded or left open.