Prisoner #95H522. Convicted November 6, 1995 - Possession of illegal substances, murder in the second degree. Sentence: Life imprisonment, up for parole in 20 years.
Mentored by his godfather Burr Redding, Hill has been selling and using drugs since his teenage years. In 1995, a SWAT team came after him on a drug warrant on a tip from a friend named Kevin Ketchum, who gave up Hill's location to avoid going to jail on an old warrant himself (this wasn't revealed until the fourth season of the show). The details of his capture are revealed in the second episode of the show. The SWAT team busted Hill's apartment door down while he and his wife were having sex. He escaped out the window and raced up to the roof. Cornered there, Hill shot and killed one of the SWAT officers. In retaliation, he was thrown off the roof by another cop and was left paralyzed from the waist down.
In prison, he remains a neutral figure until Redding shows up and takes charge of the black inmates. As Hill uses a wheelchair and is not associated with any gang members, he remains one of the more consistently decent characters on the show, struggling to avoid moral compromises while staying alive in the dangerous world of Oswald Maximum Security Prison. In the fifth season finale, Hill accidentally sacrifices himself to save Burr Redding from the Italian inmates, although he continues to show up in narration segments.
Hill is one of the inmates let into Emerald City. A wheelchair user, he poses no threat to any inmate or guard and remains a neutral figure, getting along with everyone for the most part. In Em City, he works in the dress factory with inmates such as Bob Rebadow and Tobias Beecher. Hill does not really like Beecher, as he was a lawyer on the outside, a profession Hill despises. When conjugal visits are allowed, Hill sleeps with his wife Annabella for the last time. Being paraplegic, he has no sensation below his waist so he cannot experience the pleasure received during sex. When Simon Adebisi asks him why he even wants to have sex with his wife without sensation, Hill claims it is all for her.
Hill also takes part in the drug rehab program and has been clean for almost two years. He takes a break from this, however, when his hero NBA player, Jackson Vahue, arrives in Oz and encourages him to use drugs. After using one time and seeing how much of a bad person Vahue really is, he stops using drugs.
Hill admires new inmate Eugene Dobbins, who has a gift for playing the cello. When Dobbins is harassed by Vahue for no apparent reason, Hill tells him stop and recognize the gift that Dobbins has. He even gets a fellow prisoner, who plays the trumpet, to accompany Dobbins in rehearsals. This all goes awry with Vahue breaks into the chaplain's office and smashes Dobbins' prized instrument.
Meanwhile, the tension in Em City erupts into a riot, in which Muslim inmate Kareem Said leads the takeover. Hill forces Vahue to carry out the wounded Dobbins, who gets stabbed by a black inmate during the riot and then hides with the rest of the prisoners as the SORT team recaptures the unit.
The inmates from Em City are transferred to general population, as the riot has destroyed the unit. Law school dean Alvah Case investigates the riot's causes and asks Hill several questions pertaining to its origins. Hill is then told that Eugene Dobbins died and the unit housing the inmates has become overcrowded. When Em City is reopened, Hill is let back in as an "Other" inmate with Bob Rebadow, Agamemnon Busmalis, and his new cellmate Tobias Beecher. Hill is angered and thinks Unit Manager Tim McManus should have classified him as one of the Homeboys, the black gangsters in Oz. Augustus is also wary of rooming with Beecher, as Beecher has recently bitten off the tip of inmate James Robson's penis. Hill cannot sleep with Beecher as his roommate, constantly protecting his genitalia at nighttime, and is relieved when Chris Keller arrives and replaces him as Beecher's cellmate.
In the Em City council, Hill represents the Others. Augustus then sees that his judge during the trial has been imprisoned for receiving bribes during the sentencing of various inmates. Angered, he gets Said to represent him in an attempt to free himself. Said speaks powerfully in Hill's favor but the judges and defense attorneys conclude that the judge had fairly sentenced him, as no mention of a bribe occurred during his trial. Frustrated, Hill spends the rest of the season figuring out ways of escaping Oz.