Gilber Rugtoff was brought up in the town of Phandalin by his Aunt, Qelline Alderleaf on Alderleaf Farm. Quelline rarely spoke of Gilber's mother, only that she left the town when Gilber was a child.

 
As a youth, Gilber learned he was adept at breaking into the unbreakable and climbing the unclimbable. These skills did not go unnoticed and he was quickly drawn into the Redbrand gang of bandits.

 
Gilber spent the next couple of years robbing and burgling his way through the holdfasts surrounding the Neverwinter Wood. Occasionally, he would venture to the Redbrand's headquarters in Neverwinter. GIlber became enroilded in a gang war on the street of Neverwinter between the Redbrands and the Gilded Gallows. To test his mettle, Gilber sought to infiltrate the Gilded Gallows' lair to take their most valued treasures. Gilber, in his haste, set off an arcane silent alarm in the Gilded Gallows leader's (Lysara Vale) vault and was caught in the act. Gilber narrowly escape the lair and fled the city with a target on his back - an expensive target.

 
As he returned to Phandalin, Gilber re-joined his comrades in the Phandalin gang, now led by Glasstaff. Glasstaff ordered Gilber and 2 other gand members to burgle the Drendar residence. The burglary went awry. The 2 Redbrands captured the Drendars and sought to burn the house to the ground as a show of strength. Gilber disapproved of the plan and stormed out. Glasstaff was enraged at the burning of the property, so the 2 Redbrands told him it was Gilber's plan. Giber had yet another target on his back as he set about his travels in exile. He returned to Neverwinter to make amends with the Gilded Gallows, to stumble across a quest in a nearby inn to guard a caravan of goods along the Triboar Trail...
 
Gilber's goal is to seek vengeance on the Redbrands and Glasstaff and to make peace with the Gilded Gallows.