Growing up, Gabe was your standard dupe. He ended up in trouble a lot, but not because he did anything on his own, as the neighborhood rascals knew that he was an easy to convince scapegoat. As such, there were many times where he would end up with people angry at him while his “friends“ disappeared down an alley. Gabe attempted to break off relationships with the most common “friend“, but this “friend“ was a budding sorcerer, who‘s mastered trick was an illusion that made him look like a different person, and had managed to “befriend“ Gabe as a varity of different people.
Gabe managed to finally dissuade his sorcerous friend, mostly by being extremely suspicious of anyone who was overly friendly, and by punching anyone who showed a knack for illusions. However, the fact that he ended up in fights a lot (due to his friend) he had made a bit reputation for himself, and soon ended up with a bit of a gang, consisting mostly of boys who wouldn't go away. Gabe soon found the benefits of an ally (or a distraction, at least) in a fight were invaluable and grudgingly allowed his gang to grow, and soon controlled three streets.
One day, Gabe was walking around his territory with four members of his gang when he was ambushed by eleven boys from a rival gang. A cavalier of the dragon order was passing by at the time, and was surprised to see Gabe lead his gang to victory. The cavalier walked over the Gabe and offered him what every boy dreamed of, the chance to train under a knight and eventually become one himself. After he got over his shock, Gabe accepted. Soon, dressed in some old leather armor and wielding the first weapon he came upon, a old smithy hammer, Gabe rode out on a pony with his master‘s group and the convoy they had been hired to guard.
He soon discovered, that as hard as he was from leading a gang, that the world outside the city was harder, and his master was harder yet. In the first week, Gabe earned several dozen bruises from sparring with his master. That did not deter him, as the convoy was attacked twice on the trip, and his master was always in the center of the fighting, taking blows meant for his allies and dealing back twice for every one he took. So with hero-worship giving a rosy tint to his world, Gabe attacked his training with a glee normally reserved for kids in candy shops.
After four years of training, on his nineteenth birthday, Gabe's master decided that there was nothing more he could teach Gabe, and Gabe set off on his own, looking for his own companions and adventures.