As of 2003, Sampson had been married and divorced five times, and is the father of three children. His first marriage was when he was 17 years old. In 1995, after being released from jail on a theft charge, he moved to Tamworth, New Hampshire, where he met Karen Alexander. In June 1997, Sampson and Alexander were married; she was pregnant by Sampson at the time. Shortly after, he moved to South Carolina with a woman he had recently met, and Alexander filed for divorce that same year. Sampson was arrested in May 1998, and met Amanda Newcomb while jailed. When Newcomb's grandfather posted Sampson's bail, Sampson and Newcomb married in October 1998. By the end of November, Sampson had moved to North Carolina, where he had a relationship with Ricky Carter, a transvestite who recalled him as "angry with the world and having an explosive temper." When Carter kicked him out of their apartment, Sampson met and wooed Karen Anderson in April 2001. Sampson attempted to force Anderson to assist him in his robberies; she refused, and Sampson began his bank robbery spree, robbing five banks in three months.