2001

The old man's arrival threw leadership into the works for the Homeboys. He was also like a father to Augustus Hill. However, Redding refused to ally himself with the Italians and Latinos, so Latino leader Enrique Morales killed a man and framed Redding. This failed to bring a prosecution. Redding also informed Hill that inmate Supreme Allah had ratted Hill to the cops back in 1995, thus resulting in Hill's paralysis and prison term. So Redding called old friend Tug Daniels to Oz, and Tug stabbed Supreme. He was arrested and sent to Oz. Redding allied himself with new cellmate Frank Galson, who discovered that Tug and Supreme were working together with intentions of killing Redding. Redding himself strangled Tug to death. The old man also plotted a mass murder of the Italians and Latinos, which Hill prevented by telling the officers. Angry, Redding shunned the man from the Homeboys. But when Hill killed Supreme to save Redding's life, the old man offered Hill a place in the gang again, which Hill respectfully declined.

2002

Redding learned that Hill's wife was divorcing him, and tried to comfort him. However, shortly afterward, Hill's mother was killed in a bus accident. Hill turned to a world of drugs, which gave him a kidney infection. When Redding learned that Hill had used drugs, he angrily searched for the dealer responsible. Old man Busmalis told him that he'd seen an Italian, Salvatore DeSante, deal drugs to Hill. So Redding put liquid LSD into DeSante's food, shutting down his brain and putting him into a permanent coma. However, Em City administrator Tim McManus informed Redding that DeSante hadn't given drugs to Hill. Redding and his right-hand man, Poet, confronted Busmalis, where Poet craftily forced Busmalis to claim that a Latino, Carmen Guerra, had forced him to lie. Redding and Poet attacked Morales and Guerra, resulting in many trips to the Hole. When the men returned, Redding spoke to Hill personally, and Hill refused to ever tell who'd given him drugs. However, the Latinos and Italians plotted against Redding, and Italian hitman Franc Urbano attacked Redding with a shank, but Hill was stabbed, and Redding watched helplessly as the boy died.

2003

Redding was a mess after Hill's death. McManus told him that Augustus had written a letter in case of his death, but Redding refused to read it. Redding wanted to make his men stop dealing drugs but knew that he would have to show them a new way to make money. Soon afterward he saw on the news that Devlin was planning on allowing a local small telemarketing business to be opened inside Oz. Redding immediately went to Said and asked him to back him up on volunteering their gangs. When Said heard the details of the business, he refused to allow the Muslims to be involved. Redding, however, was still very interested. He told his men about the telemarketing business, and they reacted strongly against it. He did his best to make it sound nice for them. Redding found his men doing well with the telemarketing business. However, when Poet got upset at a woman he was calling, Redding yelled at him to calm down. Poet refused to sacrifice his dignity for some "racist bitch", so Redding fired him. Most of Redding's gang walked out on the business then and there. Redding told Poet and his men that they can come back to the telemarketing business, but they refused. Redding ordered Poet and the gang not to deal, but they wouldn't listen. So Redding went to Pancamo and the Sicilians and made an arrangement: kill any Homeboys they see dealing drugs. Redding found the telemarketing business lagging, and he began to ask various inmates to try it out. All refused. When he caught one of his employees, Samuel Gougeon, preaching to a customer about God, he got mad at him. He told Gougeon to sabotage the Muslims' publishing business, which was dragging away all his possible employees. Gougeon complied. Zahir Arif angrily confronted Redding, who confessed to having done it, but then he showed Arif that what had happened was a good thing. Poet, Rawls, and Maxwell decided to go back to Redding's telemarketing business.