Theodore 'T-Bag' Bagwell

Theodore Bagwell was born of both incest and rape after his father sexually attacked his Down syndrome-afflicted sister.He was also indisposed by his father. Theodore's father is also the person responsible for his significant use of language, making him learn whole encyclopedias and dictionaries believing this would enable his son to lead a better life and maybe even become President one day. He once forced T-bag to recite 10 synonyms for 'destroy' to demonstrate his ability in front of some friends of his father. Bagwell spent his youth in and out of jail, often for vandalism and torturing animals. While in fourth grade, he attempted to set his teacher's house on fire and was sentenced to youth detention center. During this time, he became a member of the Alliance for Purity, a white supremacist group.

As an adult, T-Bag starts committing more serious crimes such as battery, assault, attempted murder, murder, rape, and kidnapping. He quickly becomes the leader of the Alliance for Purity inside Donaldson Prison in Alabama and under his leadership the gang becomes so powerful inside the prison that the warden disbands it and sends T-Bag to Fox River.

Prior to incarceration at Fox River, Bagwell eludes the authorities and pursues a relationship with a single mother named Susan Hollander, who has two children of her own from a previous marriage. This was one of the storylines featured in the first season's flashback episode, "Brother's Keeper". Upon learning that he is a wanted murderer and rapist (by watching America's Most Wanted), she notifies the police. T-Bag had genuine feelings for Susan and had tried to change, but her betrayal prompts "that old dirty bastard  right back home".