Cutty is known as a legendary soldier in Baltimore's drug trade and was finishing a fourteen-year prison sentence when Avon Barksdale and Wee-Bey Brice arrived in prison. Cutty is well respected by Avon and many others in his organization for the work he did before going to prison, including phoning the police from the scene of a daytime murder he had committed. Avon approaches Cutty with an offer of work shortly before his release. Barksdale lieutenant Shamrock gives him a homecoming gift of a package of narcotics. After observing a street dealer for a time, Cutty approaches him and offers to supply him for a cut of the profit. The dealer, Fruit, takes Cutty up on his offer but refuses to pay him when Cutty returns for the profits. Fruit then takes out a gun and threatens Cutty, leading him to back down. Cutty turns to work as a day laborer with a landscaping crew to get by. He tracks down his ex-girlfriend, Grace Sampson, to reconnect and finds her working as a schoolteacher. She puts him in touch with her church deacon to help him find work, but resists any other involvement. The deacon suggests that Cutty study to obtain his GED, but Cutty sees this as too difficult and, despite his initial hesitation, begins working with the Barksdale crew soon after his parole.