#97P904 Ryan O'Reily
#98P284 Cyril O'Reily

Ryan O'Reily is played by Dean Winters Link to IMDB
Cyril O'Reily is played by Scott William Winters Link to IMDB

Season 1
O'Reily Ryan O'Reily was convicted July 12, 1997 of two counts vehicular manslaughter; five counts reckless endangerment; possession of controlled substances; criminal possession of a weapon; and parole violation. Sentence: Life imprisonment, eligible for parole in twelve years.
O'Reily Before coming to Oz, O'Reily was shot and left for dead by fellow inmate Dino Ortolani. Ryan provokes Ortolani and gets the crap beat out of him.
O'Reily After Ortolani murdered AIDS patient Emilio Sanchez, he was thrown in the hole and sedated. In his quest for revenge, O'Reily arranged for inmate Johnny Post to get in the hole, where he set Ortolani on fire. O'Reily transferred to Em City, into Ortolani's pod.
O'Reily O'Reily becomes friendly with lawyer-turned-inmate Tobias Beecher. He asks Beecher to look into his appeal. He also gets Beecher hooked on heroin.
O'Reily Nino Schibetta tells O'Reily to shut down Officer Healy's drug business, because it's cutting into his own drug business. O'Reily arranges to have them caught. O'Reily is thrown into the hole and Healy is busted.
O'Reily Nino Schibetta puts O'Reily in charge of the kitchen after Joey D'Angelo has an "accident." O'Reily and Adebisi begin grinding up broken glass and begin lacing Schibetta's food with it. They plan to take over Nino's drug business after he's dead.
O'Reily Schibetta is still being fed ground glass by O'Reily and Adebisi, and ends up hemorrhaging. O'Reily lets him know that he fed him the glass. Schibetta soon dies.
O'Reily The 1997 Riot erupts. Said quickly takes control of the situation and gathers the other leaders, including O'Reily, to form a council to come up with their demands. Governor James Devlin sends in the SORT team.
Season 2
O'Reily O'Reily and the rest of the riot leaders are sent to ad-seg while Alvah Case heads a special committee appointed to investigate the riot. Case's Commission determines that no one in particular was at fault for the riot and O'Reily is sent back to gen-pop.
O'Reily New inmate Peter Schibetta takes over the kitchen by cashing in a favor Glynn owes the family. O'Reily tells Peter that Adebisi killed Nino by putting ground glass in his food. ("All rats know when to abandon a sinking ship.")
O'Reily O'Reily's right nipple begins leaking a brown fluid. Dr. Nathan runs tests and he is diagnosed with breast cancer. He is taken to a hospital to get a prison-paid lumpectomy, which is cheaper than a mastectomy. He begins chemotherapy. Mistaking her compassion for love, O'Reily is convinced he's in love with Dr. Gloria Nathan.
O'Reily O'Reily arranges to have his mentally impaired brother Cyril kill Nathan Preston, Dr. Nathan's estranged husband. Cyril is caught, convicted, and imprisoned in Oz. In order to keep him away from Schillinger, Ryan picks a fight with Cyril and Cyril is sent to the hole.
O'Reily O'Reilly arranges for Adebisi to meet Shirley Belanger.
O'Reily When inmate Miguel Alvarez attacks C.O. Rivera, he leaves the victim in need of a blood donor. Ryan O'Reily is the only person in Oz with AB negative blood. He agrees to give blood if they let Cyril out of the hole and move him into Em City. He finally admits that he had Cyril kill Nathan Preston.
Season 3
O'Reily Cyril has continuing nightmares about being raped by Vern Schillinger. Ryan begins looking for a way to get back at Schillinger.
O'Reily Ryan arranges with Jaz Hoyt to have a package containing brass knuckles move through the mail room. Vern busts Hoyt and Hoyt tries to kill him, but fails.
O'Reily Ryan gets 40 years added to his life sentence when he confesses to having Cyril kill Preston Nathan.
O'Reily Cyril lands in the hole when James Robson provokes him.
O'Reily Head C.O. Sean Murphy arrives to take Metzger's place. Officer Murphy and Tim McManus begin preparing for a boxing match. O'Reily looks to Officer Murphy's help in training Cyril.
Robson and Schillinger tease Ryan O'Reily mercilessly over their raping Cyril.
Aunt Brenda Aunt Brenda comes for a visit. When she finds out that Cyril is boxing, she gets on Ryan's case. He tells her to drop dead.
O'Reily O'Reily has Christian inmate William Cudney steal chloral hydrate from the infirmary. O'Reily spikes James Robson's water to ensure that Cyril will win.
O'Reily When Vern's son, Andrew Schillinger, lands in Emerald City, he gets in on Beecher's plan with Keller. Ryan makes sure that he keeps Andrew supplied with heroin.
O'Reily Ryan rubs Vern's nose in the fact that his kid is a junkie, pointing out that Andrew is passed out face down in his food.
Ryan cuts off Andy's drug supply... Andy won't buy from anyone who's not white. Andy goes through withdrawal, but Beecher is conveniently there to help him through it.
O'Reily Ryan continues to manipulate the boxing matches. Cyril continues to win.
O'Reily Still having feelings about Dr. Nathan, Ryan tries to scrub the tattoo of his ex-wife, Shannon's name off his arm.
O'Reily When Cudney threatens to spill the truth about Cyril's "wins," Ryan solicits Yuri Kosygin's help. Kosygin kills Cudney and Ryan drugs Pancamo's water with heroin. In order to eliminate both Kosygin and Stanislofsky, Ryan has Stanislofsky tell Pancamo that Kosygin was the one drugged him. Ryan then tells Kosygin that Stanislofsky was the one who ratted on him; Kosygin stabs Stanislofsky and Kosygin ends up in the hole.
O'Reily Ryan and Cyril's father visits, giving Cyril inspiration in the upcoming fight.
O'Reily Stanislofsky tips Officer Murphy about Ryan's cheating and Murphy catches Ryan in the gym drugging Khan's water. Cyril has to fight Khan fair and square.
O'Reily Cyril wins the tournament, but Khan is left irreversibly brain dead. When Cyril finds out that he made Khan like him, he attacks Ryan.
Season 4
O'Reily Cyril has continuous nightmares about the murder of Nathan Preston and what he did to Hamid Khan.
O'Reily Ryan consults with Sister Pete about Cyril's nightmares. Sister Pete suggests that Ryan and Cyril meet with Gloria Nathan and Preston's parents, Lars and Patricia. When Sister Pete first brings the idea up to Gloria, she objects.
O'Reily In order to talk with Dr. Nathan, Ryan cuts his hand. Ryan asks Dr. Nathan about Hamid Khan, but she sees through him.
O'Reily After speaking with her in-laws, Gloria decides to go forward with the sessions. During Sister Pete's first session with Cyril and Ryan, she asks them what they would like to say. Cyril wants to ask them to be his "friend." Ryan doesn't really seem to care.
O'Reily Cyril asks Ryan why he doesn't use his cell phone instead of the pay phone, like the funny Russian guy. Ryan confronts Stanislofsky about the cell phone. Of course, Nikolai doesn't know what he's talking about. Ryan later searches Stanislofsky's pod for the phone, but can't find it.
O'Reily Stanislofsky knows that Ryan couldn't find the phone...if there was a phone.
O'Reily Ryan finds out where the cell phone came from. He tells Ralph Galino that he shouldn't have trusted their good friend Nikolai, who has kept the phone for himself. When Galino demands that Stanislofsky return the phone, Stanislofsky arranges for Galino's pod-mate, Jaz Hoyt, to kill him.
Stanislofsky Ryan tells Nikolai that he has underestimated him and Ryan proposes that they work together. They shake on it. They share the cell phone...
The Nathans Ryan and Cyril participate in Sister Pete's interaction program with Dr. Nathan and Preston's parents, Lars and Patricia Nathan. It does not go well. Ryan tells Dr. Nathan that he did it because he loves her. On her way home, Gloria is raped.
Gloria Upon returning to Oz, Gloria confronts Ryan about the rape. He tells her that he had someone do it and she flys at him in rage. Sister Pete is convinced that Ryan is lying.
Hoyt and Stanislofsky O'Reily tells Hoyt that Stanislofsky had him kill Galino because Galino had a cell phone that Stanislofsky is not sharing. Hoyt attacks Stanislofsky. Hoyt is thrown in the hole and Stanislofsky is thrown into solitary....
O'Reily Ryan ends up with the cell phone all to himself.
O'Reily Stanislofsky tells Em City admin Martin Querns that Ryan O'Reily has a cell phone. A search turns up nothing.
O'Reily Stanislofsky has his girlfriend call the cell phone number. O'Reily claims ignorance.
O'Reily Cyril overdoses on Haldol and slips into a brief coma. They change his medication.
Keenan New inmate Patrick Keenan brags to O'Reily about raping Gloria Nathan.
O'Reily Ryan takes care of Keenan... all for Gloria. Ryan doesn't notice that Arif saw him kill Keenan with the weight. Ryan sends Gloria an envelope with Keenan's necklace and a note that says "All for you Gloria." Gloria takes a leave of absence.
O'Reily Ryan begins having an affair with psycho Officer Claire Howell.
Stanislofsky Ryan asks Officer Howell take care of Stanislofsky. Psycho Claire is more than happy to lending a helping hand. While in the whirlpool in the infirmary, she gives Stanislofsky a hand job and then throws a blow dryer into the water.
O'Reily Keller realizes that they have to get rid of Adebisi. He enlists Ryan O'Reily's help. O'Reily steals Supreme Allah's necklace while he's in the shower to use as "evidence."
O'Reily Ryan continues to have sex with Claire in the ladies' bathroom.
O'Reily Cyril realizes something is going on with Ryan and Claire. Ryan tells Sister Pete that he needs to be tranquilized because he's "talking crazy." Sister Pete has a chat with Cyril and she asks him about his mother. He remembers her praying. Sister Pete asks if he believes in God, and Cyril replies "We don't choose God. God chooses us." This simple statement pulls it all together for Sister Pete, who decides to not leave the convent.
O'Reily Ryan trys to put a stop to sex with Claire. She tells him that it's up to her when they stop.

"Same time tomorrow. Cunnilingus."
O'Reily Keller murders Shemin and Mondo Browne. He and O'Reily pin the murders on Supreme Allah. This sets off a chain of events that ends up with Warden Glynn firing Querns. Adebisi attacks Said and Said kills him in self-defense.
Season 4 (Part II)
Eldridge January 2001.

TV News reporters Lisa Logan and Jack Eldridge arrive at Oz to do a story. Jack Eldridge did a story on street gangs 20 years ago. It depicted how the African-American gangs were displacing the Irish gangs. Ryan and Cyril were featured, and Jack made them look bad.
O'Reily At the drug counseling session, Keller makes up a sad story about why he uses drugs. Beecher scoffs: "He's just acting for the camera." Ryan tells Beecher to shut up and Beecher makes a comment about Keller and O'Reily being "butt buddies ever since who died?" Sister Pete breaks them up before a fight begins and makes Logan turn the camera off.
Keller Ryan tells Keller that they have to take care of Beecher before he tells the media about Shemin and Browne.

"You hurt Beecher, I may have to hurt you."
O'Reily O'Reily notices that new inmate Omar White is going through detox and can't get drugs. He takes advantage of the situation.
O'Reily O'Reily tells White that if he wants to oust Poet as leader, he needs to kill someone. Someone famous....
O'Reily Eldridge interviews Ryan O'Reily about Adebisi's death. Ryan tells Eldridge that they met 20 years ago. He refuses to continue the interview until he is paid. Eldridge balks.
O'Reily Jack Eldridge is to spend the night in a cell with Omar White as part of the story. O'Reily convinces homophobic White that Eldridge is going to humiliate him on national TV by telling everyone that he is a "cocksucker."

Unfortunately for Ryan, White doesn't wait until they're alone in the pod, but tries to kill him right away. He fails. White is thrown into solitary.
O'Reily Cyril is chosen to spend the night with Eldridge. Unfortunately for him, Cyril didn't take his medication.
O'Reily While talking with Jack Eldridge, Cyril begins having flashbacks to the story 20 years ago. Cyril remembers parts of the story and that his mother cried and slapped Ryan.
O'Reily Yelling "You gave my mama cancer," Cyril beats the crap out of Jack Eldridge, until the SORT team carries Cyril away to the infirmary.
O'Reily "Please tell me you got that on tape!"

The station decides not to air the show. Lisa Logan quits her job.
O'Reily Over a game of chess, O'Reily tells Keller that he's been having sex with Claire Howell.
O'Reily Claire has O'Reily thrown into the hole, where she has her way with him.
O'Reily Dr. Nathan arrives back to work after taking a few months off. During a checkup, Cyril tells her that he wishes that he could have taken time off after he got raped.

Dr. Nathan is having trouble finding the right combination of medicine to help Cyril.
Claire Psycho Claire Howell tells Dr. Nathan that she's been taking real good care of Ryan O'Reily while she's been away.
O'Reily Ryan ends up in the infirmary with bad chest congestion (he caught a cold while having sex with Claire in the hole). Gloria asks him about Keenan's necklace. He admits to killing him because he raped her. Ryan tells her that he loves her.
Nathan Dr. Nathan confesses to Sister Pete that she loves Ryan O'Reily.
O'Reily O'Reily tries to break it off with Claire again. She tells him she'll go after Cyril if he tries to stop it.
O'Reily Cyril gets into a fight with an Aryan over the phone. Cyril is dragged down to the infirmary kicking and screaming. When Dr. Nathan attempts to sedate him, he grabs her by the neck and tries to choke her until he is knocked unconscious by a C.O.
O'Reily Ryan convinces Dr. Nathan to let him and Cyril participate in an experimental aging drug study. (Participants get reduced prison time.)
O'Reily Cyril begins to feel the effects of the aging drug. Ryan tries to convince everyone to quit, but they ignore him. After Wick dies, the drug test is canceled.
O'Reily When Supreme Allah returns to Em City, Ryan probes him for information. Supreme has figured out that Keller and O'Reily framed him. Lucky for them, Burr Redding already has it out for Supreme.
O'Reily Suzanne Fitzgerald claims to be Ryan's birth mom. He doesn't believe her and stomps off.
O'Reily Claire Howell has grown bored with Ryan. She dumps him.
O'Reily Claire sets her sights on Cyril, who yells "You're not allowed to touch me!" and slams a tray into her face. The CO's pound him and there is talk of sending him to the Conley Institute (the "looney bin").
O'Reily Ryan asks his father to visit. He tells him that Cyril may be transferred to the Conley Institute. (He doesn't care.) When Ryan asks about Suzanne Fitzgerald, he gets pissed and stomps off.
O'Reily Ryan asks Dr. Nathan to help him and Cyril and not send Cyril to the Conley Institute and to contact Suzanne Fitzgerald and ask her to come back.
O'Reily IRA terrorist Padraig Connelly arrives in Oz, arrested for illegal entry into the US. Connelly doesn't have much use for Ryan.
O'Reily Suzanne Fitzgerald returns and tells Ryan that she left when he was three months old because she couldn't live with his father. She tells him that she is not Cyril's mother; Cyril is his half-brother.
O'Reily Jia Kenmin shows off his martial arts moves and knocks Ryan down to the ground. Cyril responds by beating him into a coma.
O'Reily Dr. Nathan convinces that Cyril should be transferred to protective custody, not to the Conley Institute. McManus and Sister Pete agree.
O'Reily Ryan asks Dr. Nathan to help him and Cyril escape.
O'Reily Cyril waits in protective custody for Ryan to visit.
O'Reily Officer Howell tries to blackmail Ryan. She tells him that she'll make sure that Cyril is not transferred to the Conley Institute if Ryan lets Claire have her with with Cyril.
O'Reily Ryan asks Alvin Yood to take care of Howell. He trips her on the stairs and she breaks her pelvis.
O'Reily Ryan intervenes when Kirk and Burns gang up on Padraig Connolly to get him to convert. He brings Jeremiah Cloutier with him and Cloutier casts Kirk out of his congregation.
O'Reily Ryan's mother, Suzanne Fitzgerald, visits and tells him of her past, why she left, and how she is running from the law because someone was killed during an anti-war demonstration. She is going to turn herself in. Ryan tells her of their plan to escape, but she tells him that running for his entire life is no way to live.
O'Reily Dr. Nathan returns Patrick Keenan's necklace to Ryan. She tells him that she will not help him escape and if he asks again, she will tell the warden everything.
O'Reily Ryan tells Connolly that he wants to do something to "make a difference." Connolly asks if he's willing to die for the cause. Ryan begins gathering supplies for Connolly, including 2 gallons of bleach and a watch.

"We're gonna blow up Em City."
O'Reily Ryan gets the final piece to Connolly's bomb.
O'Reily Dr. Nathan has Cyril returned to Em City. Ryan shows his gratitude by kissing her.
O'Reily Feeling high on life, O'Reily tells Connolly that he is having second thoughts about blowing up Em City. When Connolly won't back down, Ryan leaves the kitchen (with the gas on) to get the bomb.
Connolly Connolly gets the bomb and arms it. Em City is evacuated, but the bomb is a dud.

However, when a hack lights up a cigarette in the kitchen, the gas O'Reily left on causes an explosion.
Season 5