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Was confronted by Peter Schibetta in the gym one day and was asked about the death of Nino Schibetta. Ryan, in a heartbeat gave up Adebisi. Ryan told The Wiseguys that it was completly Adebisi's idea and that he was trying to kill Adebisi. Ryan told Peter that he and Peter's father were friends and they helped eachother out. Ryan told Peter that he hopes they can have the same kind of relationship. One day in the gym, Ryan's nipple started bleeding. Ryan went to Dr. Gloria Nathan who was baffled. After hours of researching, Dr. Nathan thought that it could be male breast cancer. Ryan was outraged by Dr. Nathan telling him this. He took it as her telling him he's less of a man. Ryan got the lump under his breast removed and started receiving kimo-therapy. Ryan was visited by his brother Cyril and his wife who is getting sick of taking care of Cyril. Ryan broke up with his wife and sent Cyril to live with his cousin. Ryan went back to Em-City very weak and sickly looking. Ryan got into a fight in the cafeteria and instead of placing him in the hole, McManus opted to keep Ryan in the hospital since he was in bad shape and he didn't want to risk Ryan getting sicker and dying in the hole. Ryan soon developed a love for Dr. Nathan. Once, Ryan grabbed Dr. Nathan and kissed her. Ryan became so infatulated with Dr. Nathan that he had his slow brother Cyril kill Dr. Nathan's husband. When Cyril was arrested for the murder, Dr. Nathan wanted nothing to do with Ryan. Cyril refused to implicate Ryan in the murder of Preston Nathan. After Cyril was raped by Shillinger, Ryan has Cyril punch him in the face which landed Cyril in the hole and away from Shillinger. Ryan tried desperatley to get Cyril transferred to Em-City. McManus explained that the only way he'll ley Cyril in Em-City is if Ryan will admit that he sent Cyril to kill Preston Nathan. Ryan refused to admit that he sent Cyril to kill Dr. Nathan's husband. When officer Rivera's eyes were plucked out by Miguel Alvarez, he was in desperate need of a transfusion but all te blood banks were out of O-. The only person in Oz with O- blood was Ryan O'Reily. O'Reily refused to give his blood until his brother Cyril was re-located to Em-City. While laying bed after giving his blood, Ryan thought about his brother and decided to confess to sending Cyril to kill Preston. Ryan said that it's time for him to be a big brother for once to Cyril. He also told the story of how Cyril became slow. Ryan got the two into a fight during a wake and Cyril got hit in the back of the head with a large piece of wood. This incident left Cyril with the mind of a 5 year old. By the end of the season, Ryan was back to his old ways, crossing everybody.