|First appearance||"The Routine" (episode 1.01)|
|Last appearance||"Exeunt Omnes" (episode 6.08)|
|Reason/Cause||End of Series|
|Date of Conviction||July 12, 1997|
|Affiliations||The Irish & Bridget Street gang|
|Spouse||Shannon O'Reily (Divorced)|
|Relatives|| Cyril O'Reily (Half-Brother, deceased)|
Seamus O'Reily (Father)
Tessie O'Reily (Stepmother, deceased)
Suzanne Fitzgerald (Birth Mother)
Brenda O'Reily (Aunt)
Carolyn O'Reily (Sister, deceased)
|Episode Count||56 Episodes|
|Portrayed by||Dean Winters|
- "I never lose when it counts."
- ―Ryan O'Reily[src]
- "Prisoner number 97P904, Ryan O'Reily. Convicted July 12, '97 - Two counts of vehicular manslaughter, five counts of reckless endangerment, possession of a controlled substance, criminal possession of a weapon, parole violation. Sentence: Life imprisonment, up for parole in 12 years."
- ―The Narrator[src]
O’Reily is an Irish American hoodlum originally sentenced to 12 years to life for killing two people while driving under the influence of drugs and alcohol, then 40 to life after confessing to a murder he had his brother, Cyril, commit. Before he was arrested for his original crime he was running a street gang of Irish American hoodlums called the Bridget Street gang, with Cyril as his lieutenant/bodyguard. When his brother is permanently brain-damaged in a fight with a rival at a funeral, Ryan, blaming himself, goes on a drug and alcohol-fueled rampage throughout the city.
Highly intelligent and completely ruthless, O'Reily survives in Oz by manipulating everyone around him, and working with the most dangerous inmates using a variety of inmate gangs to get whatever he wants; series creator Tom Fontana has likened him to Iago, the villain of Shakespeare's Othello.
Ryan is extremely protective of his brother Cyril, and has no qualms with striking against anyone who threatens him, including guards. Above all else, Ryan strives to keep Cyril in Em City where Ryan can defend him. Cyril in turn cares about Ryan and depends on him a great deal, usually obeying him, which has led to Ryan taking advantage of him more than once.
As soon as he arrives in Oz, he starts plotting revenge against Dino Ortolani, an Italian inmate who attempted to kill him a year earlier but failed. He attempts to set a hit on Ortolani through the Homeboys, but their leader, Jefferson Keane, tells him that they don't kill wiseguys. Instead, O'Reily goes to Mike Healy, a correctional officer who is friendly with O'Reily. Healy tells O'Reily that Ortolani is on a destructive path and will likely do something to get himself killed soon. Healy's suspicions are confirmed when Ortolani gives a severe beating to Keane's brother Billie. O'Reily uses this to his advantage and brokers a deal with Keane to have Ortolani killed. Later, a hitman for the Homeboys, Johnny Post, arrives at Ortolani's solitary cell. He bribes the CO in solitary, then enters Ortolani's cell and murders him by setting him on fire.
With Ortolani out of the way, O'Reily sets his sights on taking over the drug trade in Oz. The drug trade is primarily handled by two entities - the Italians, led by Nino Schibetta, and the Homeboys, led by Jefferson Keane. O'Reily realises that in order to assume control over the drug trade, he'd need to take both of them out of the picture. Meanwhile, Schibetta starts a manhunt in Oz seeking to avenge Dino Ortolani, who was his nephew and right-hand man. O'Reily catches wind of Schibetta's investigation and attempts to persuade Keane to betray Post and sell him out to Schibetta. Keane denies O'Reily, stating that he'd never betray his soldiers.
Schibetta notices O'Reily with Keane and suspects that O'Reily and Keane may be working together. He orders the lead investigator on Ortolani's murder, Lenny Burrano, who is also on the Mafia's payroll, to sweat a confession out of O'Reily. Schibetta's plan succeeds, and O'Reily later approaches Schibetta to betray Post. Post is tortured and murdered by the Italians, and his death ignites a war between the Italians and the Homeboys. However, this works in O'Reily's favour as the two main groups who he needs out of the way will likely kill each other off and he can take over. In the midst of the war, O'Reily meets with disgraced former attorney, Tobias Beecher, in the library and persuades him to help him get on appeal on his case, as he believes his original lawyer did a poor job representing him at his trial.
O'Reily then tells Healy to threaten Keane to not betray him. Later, O'Reily visits Beecher to see how his appeal is coming along and notices Beecher had been crying. O'Reily offers Beecher some drugs and the two get high. O'Reily would later offer Beecher heroin, which Beecher would get an addiction to and become O'Reily's first customer in the drug trade. Later, O'Reily is visited by Keane, who has converted to Islam and is now a Muslim, about confessing for the deaths of Post and Ortolani. Keane tells O'Reily that he wouldn't turn O'Reily in, but that they both needed to turn themselves in for being the cause of Post and Ortolani's death. O'Reily takes what Keane said as a threat and, fearing that Keane was likely going to betray him, instead betrays Keane to Schibetta by telling Schibetta that Keane ordered Ortolani's murder.
O'Reily, in an attempt to clear himself of any further suspicions that Schibetta may still have about him, offers to arrange for Keane to be killed. Schibetta accepts O'Reily's deal, and O'Reily sets up a plan with Healy's help. Keane is taken by Healy to the gym, where two Latino inmates are waiting for him. Despite Keane's pleas to not fight, they attack him and Keane defends himself by subduing one, and killing the other. Unbeknownst to Keane, the COs had been videotaping the showdown from the windows. Keane is framed for the murder of the Latino inmate, sent to death row, and eventually executed.
With Keane dead and the Homeboys in disarray, O'Reily shifts his focus to taking out Schibetta and the Italians. O'Reily notices the Homeboys, now under the leadership of Paul Markstrom, attempting to form an alliance with Schibetta. O'Reily approaches Schibetta and offers his assistance to Schibetta after overhearing Markstrom's plan of gaining Schibetta's trust and then killing him and taking over. Schibetta, however, suspects Markstrom of not being who he says he is and baits Markstrom into a trap. He reveals to Simon Adebisi, Markstrom's lieutenant, that Markstrom is an undercover cop. Adebisi murders Markstrom in response and assumes control over the Homeboys. After Adebisi takes control, he forms a real partnership with Schibetta. In the meantime, Schibetta discovers O'Reily's drug connection.
Schibetta summons O'Reily and tells him that he knows that O'Reily has been running drugs, and advises him to betray his drug source, Officer Healy, because O'Reily and Healy's operation is cutting into his profits. O'Reily co-operates with Schibetta and stages a drug bust with the help of Ronald Poklewaldt. Healy is fired for trafficking drugs into Oz and O'Reily is taken to the hole and, after telling McManus that he wouldn't testify against Healy, is forced to stay there for one month.
When O'Reily returns from the hole, he has detoxed from heroin, which doesn't last long as he starts using the remainder of his supply with Beecher. Meanwhile, Adebisi informs his new lieutenant, Kenny Wangler, that he desires to kill Schibetta and O'Reily and take over the drug trade entirely. O'Reily starts working odd jobs for Schibetta and more-or-less becomes his new right-hand man with the absence of Joey D'Angelo, who O'Reily was also responsible for taking out of commission. Schibetta rewards O'Reily for his loyalty and gives him control of the kitchen after Adebisi had been abusing his privileges.
Adebisi tells the other Homeboys to not follow O'Reily's orders in an attempt to relent against Schibetta's decision. O'Reily then makes a deal with Adebisi since they both have the same goal, which is to sever Schibetta's monopoly over the drug trade and take it over. O'Reily tells Adebisi that they can get rid of Schibetta by grinding up glass and placing it in his meals and over time it would eviscerate his insides. Adebisi agrees to the deal. O'Reily smashes a glass cup, then grinds up the broken glass, which he and Adebisi place in Schibetta's meal. Schibetta begins having stomach pains later but shrugs them off.
Later, O'Reily interrupts a meeting Schibetta is having with Kareem Said. After being told to leave by Schibetta, O'Reily is approached by Scott Ross. Ross asks O'Reily what he thinks is going on with Said. O'Reily tells Ross that he's heard rumours about the Muslims preparing to start a riot, and that they're heavily armed. Ross tells O'Reily that they should work together in case the Muslims decide to make a move against them, and suggests that O'Reily gets Adebisi on board with them. As they prepare Schibetta's meal, O'Reily asks Adebisi for confirmation that he will be on his side if Said tries to start a riot. Adebisi mentions that he has O'Reily's back. O'Reily then takes Schibetta's meal out to him, which he refuses to eat. Schibetta tells O'Reily to tell Adebisi that he's got a large shipment of heroin arriving soon and that the Homeboys should be ready for it.
When correctional officer Lawrence Smith is accidentally murdered by Donald Groves, many of the officers beats several prisoners in retaliation. O'Reily is one of the prisoners, as he is brutally beaten in front of all the prisoners in Emerald City by one correctional officer. He is then taken to the hospital and recovers quickly.
Later on in Em City, as O'Reily plays pinochle with Schibetta, he notices that Schibetta's nose is bleeding, then suddenly, Schibetta begins bleeding profusely from his ears and mouth. Schibetta is taken to the hospital ward. O'Reily and Adebisi assume control over his operation. They confront Said in the library and inform him that any business he had with Schibetta now goes through them. Later, O'Reily visits Beecher's cell and tells him that the Muslims are planning to riot at any moment and that he needs Beecher on his side. O'Reily then meets with Ross and confirms their strength in case the Muslims turn on them. Since the doctors said that Schibetta has a chance of recovery, O'Reily continues to lace Schibetta's meals with glass until eventually Schibetta completely succumbs and bleeds to death.
Later in Em City, two inmates start a fight over a game of checkers, which escalates quickly into a full-scale riot. O'Reily and Ross attack Officers Hunt and Armstrong in the entrance of Em City and overpower them. The riot goes on for a few minutes before Said fires a handgun off at the ceiling to get the inmates' attention. O'Reily meets with Said, Ross, Adebisi and Alvarez, and is appointed as one of the riot leaders. O'Reily, Ross and Adebisi are placed in control of the entrance gate. Hill and Vahue approach the gate with the intent of letting Dobbins outside, so he can receive medical attention. O'Reily, Ross and Adebisi all vote to let Dobbins out, and O'Reily tells Ross and Adebisi that they can control the situation as long as they vote with each other.
Throughout the riot, O'Reily is one of the voices of reason. He defuses several situations and confrontations. He is the one who gives the inmates' list of demands with the exchange of Officers Mineo and Armstrong. He also later informs Said that the Homeboys have run out of heroin and are beginning to become violent. Eventually, the prison officials make their move and SORT teams arrive at the entrance gates of Em City to reclaim the unit. O'Reily and Beecher hide in a cell and watch as the SORT teams arrive. When O'Reily sees a tear gas canister fly over the entrance gate, he hides in a corner using a mattress for cover.
In the second season, O’Reily is enjoying his new status in the Oz drug scene when he is diagnosed with breast cancer. He is helped through his treatment and chemotherapy by Dr. Gloria Nathan, Oz's chief physician. O’Reily falls in love with her and is so overcome with jealousy of her husband that he tells his mentally handicapped brother, Cyril, to kill Dr. Nathan's husband.
Cyril is arrested and sent to Oz, but is put in a different unit from his brother. There, Cyril is raped by Vern Schillinger and his Aryan Brotherhood gang. This enrages O’Reily, but he can't do anything about it. In order to protect Cyril, he asks the manager of his unit, Tim McManus, to transfer Cyril into "Em City" with him. McManus agrees in return for O’Reily's admission of guilt in Preston Nathan's death, which O’Reily refuses.
Later, when a guard is blinded by Miguel Alvarez and needs a blood transfusion, it turns out that O’Reily is the only prisoner in Oz to match his blood type. He uses this as leverage to secure a place for his brother in Em City with him. O’Reily then admits his guilt in Preston Nathan's murder so that he can remain in Oz to protect Cyril. McManus then informs him he will be brought up on charges for ordering the murder of Preston Nathan.
Still eager for revenge on Schillinger, Ryan manipulates Jaz Hoyt into attacking Schillinger, but Schillinger escapes unharmed. Furious, O’Reily joins forces with Tobias Beecher and Chris Keller, two other inmates who are looking to get even with Schillinger. When Schillinger's son Andrew comes to Em City, O’Reily tortures him when he stops selling him drugs, forcing Andrew to buy them through non-white inmates. Because Andrew has been trained as a member of the Aryan Brotherhood, he can't bring himself to buy drugs from those inmates. After Andrew publicly embarrasses his father, Schillinger gives his son enough heroin to overdose as a kind of test - which he "fails" by dying.
Meanwhile, the prison administrators hire a new CO supervisor, Sean Murphy. Murphy and O'Reily bond over the Spanish Armada myth of the Black Irish and develop a kind of friendship. When Murphy organizes a boxing tournament, O’Reily enters Cyril. To ensure Cyril's victory, he spikes his opponents' water bottles with chloral hydrate. Cyril beats James Robson in the first round. As a result, Ryan wins money in the bets and the Aryans leave Cyril alone for good. From there, Ryan then spikes Miguel Alvarez's water and tells Alvarez's opponent, gay inmate Jason Cramer, that the Latinos will rape his lover if he loses the fight. Alvarez loses, the Latinos look worse, and Carmen Guerra grows suspicious of O’Reily's winning streak. In round two, Cyril must fight Italian inmate Chucky Pancamo. O'Reily arranges the death of William Cudney, who threatened to expose him for cheating, and spikes Pancamo's water with heroin. Cyril easily beats Pancamo.
Murphy discovers O’Reily cheating thanks to a tip from Nikolai Stanislofsky, and tells O'Reily to stop to prevent a riot. In order to allow Cyril to keep his edge and win the final fight against Muslim inmate Hamid Khan, O’Reily invites their abusive father to visit him and Cyril. Ryan then encourages Cyril to think about their father's abuse during the fight. Pushed into a rage, Cyril beats Khan into a coma, making him brain dead. The resulting racial tension forces Oz into a lockdown.
Season 4, Part I
O'Reily and Cyril participate in an interaction session with Gloria Nathan and her deceased husband's parents. Nathan wants him there to condemn him for killing her husband, but O’Reily turns the tables on them when he says that she and McManus had an affair. She is later raped by Irish hoodlum Patrick Keenan, and she suspects O’Reily of setting her up. Although he didn't, he tells her that he did so she can feel whole again. O'Reily then kills Keenan. Nathan takes a leave of absence shortly after.
In Em City, white and Latino inmates and guards are constantly being traded for black guards and inmates who support Adebisi, so O’Reily and Keller unite to turn the tables. They murder inmates Nate Shemin and Mondo Browne, and frame Supreme Allah. As a result, Unit Manager Martin Querns is fired and McManus is rehired.
Season 4, Part II
A television crew comes to Oz to film the prisoners' daily lives, headed by Jack Eldridge, a reporter who once reported on Irish gang activity in general and the O'Reilys in particular. This report exposed them as criminals to their mother, who was emotionally devastated upon finding out. In his interview with Eldridge, O'Reily gets some revenge on Eldridge by refusing to give any information about Adebesi's death.
Dr. Nathan returns, admitting that she does indeed have feelings for O’Reily.
Supreme Allah is released from solitary and tells O’Reily that he knows who framed him, so O'Reily and Keller go to Burr Redding and ask that he be eliminated. Redding then has Tug Daniels stab Supreme Allah.
A woman named Suzanne Fitzgerald comes to visit, claiming to be O’Reily's birth mother. O’Reily does not believe her at first, but accepts it after his father tells him about her. His mother turns out to be a 1960s radical on the run and is looking to settle down.
Asian inmate Jia Kenmin and Cyril fight, putting Jia into a coma. The staff threaten to send Cyril to a mental institution. Meanwhile, Provisional IRA member Padraig Connolly arrives and plans with O’Reily to blow up the prison. At the last minute, O'Reily decides that it is wrong and that many people including his brother and Doctor Nathan may be harmed, but Connolly attempts to set off the bomb early. The bombing is unsuccessful, and O’Reily goes unpunished.
O’Reily's mother turns herself in and Governor James Devlin reduces her charge to a two-year community service sentence at Oz. Inmate Li Chen arrives shortly afterward, and Jia Kenmin plots with him to put the O’Reily brothers on death row. He persuades inmate Glen Shupe to lie to Cyril about Chen raping Suzanne after coming out of his coma. Cyril then stabs and kills Chen while defending his brother, and stands trial for murder. The O’Reily family decides that Cyril is too mentally scarred to live, so they do not oppose his trial.
O’Reily, in the meantime, shares a cell with Father Daniel Meehan, an Irish-American priest imprisoned for his part in a violent protest, who helped prison psychiatrist Sister Peter Marie Reimondo fight for Cyril's life. After finding out that Shupe was paid to lie, O’Reily plots revenge. Picking up on the grudge between Kemin and Enrique Morales, O’Reily makes a deal with the Latinos. The Latinos agree to horribly injure Shupe, making sure it won't be traced back to O’Reily; in return, O’Reily agrees to cover their tracks as well. The Latinos take off Shupe's arm, and O’Reily provokes Kenmin into a fight where he ends up aiding the guards restrain Kenmin. He convinces officer Robinson that Kenmin talked badly of the guards and, as a result, they kill him in the solitary confinement ward.
Motivated by O'Reily's previous bad blood with the Aryans, O’Reily and Poet announce in the cafeteria that Aryan James Robson had the gums of a black man surgically implanted, with O'Reily citing aloud that he "turned in his white smile for a pair of dirty ghetto gums", and the whole cafeteria erupts in laughter. Robson is kicked out of the Brotherhood for his "black blood", leaving him defenseless from the other prisoners.
With Meehan's guidance, O’Reily opens up about his childhood traumas and, after a while, finally joins the effort to save Cyril. His brother is nevertheless sentenced to death. O’Reily vows to be there in the appeal process.
O’Reily forces Shupe to tell the truth to Cyril's attorney Arnold Zelman, who is unable to get him to testify. Shortly afterward, Meehan dies from a brain embolism, Ryan then washes the body in the morgue, reading a piece from the bible out of respect for Meehan. Peter Schibetta, the son of Nino Schibetta, (the former leader of the Italian gang who was killed by O'Reily in the first season), is rumored to have killed him by giving him "the evil eye"; in return for O'Reily having killed his father, Schibetta vows to curse everyone O’Reily loves. O’Reily goes to Chucky Pancamo and tells him that Schibetta plans to use the evil eye on the superstitious Pancamo as revenge for his failure to protect him from his brutal rape from Adebisi. Enraged, Pancamo and the Italians have Schibetta killed, notably removing his eye. It's throughout this season that Zelman unsuccessfully appeals Cyril's case.
Jahfree Neema, a former Black Panther, is sent to Oz and turns out to be connected romantically to Suzanne. He initially hates O’Reily, who tries to get Redding to murder him. Neema, however, tells O'Reily that he wants to save Cyril, and he organizes every inmate from every gang to protest the execution, resulting in a last second stay of execution and as a result, Ryan gains respect for him. O'Reily also believes God saved Cyril because of his sincere prayers on what was meant to be the night of Cyril's execution.
Meanwhile, their father, Seamus, arrives in Oz and tries to kill Neema, but ends up in the hospital instead. Eventually, Cyril is executed despite Ryan's efforts, it's during the execution that Ryan is seen walking the maze in the gym unsupervised and visibly upset. It's here that Dr. Nathan enters the gym and kisses O'Reily passionately, which Ryan reciprocates, the screen then fades to black, leaving the two.
Seamus O'Reily, while in the hospital, has come to regret how he treated his sons (with the help of a stern speech given to him by Suzanne) and asks Ryan if he can see Cyril, Ryan tells him it's too late as Cyril has already been executed, the father and son then reconnect through their grief.
Ryan O'Reily is last seen wheeling Seamus onto a bus during an attack involving a mysterious contaminate orchestrated by Keller.
- Two Construction Workers: Accidently killed when he ran them over with his car. (1997)
- Patrick: Accidently killed when he crashed his car. (1997)
- Nino Schibetta: With Simon Adebisi, placed ground up glass in his meals every day until he died of internal hemorrhaging. (1997)
- Patrick Keenan: Bashed the back of his head open with a free weight. (2000)
- Supreme Allah: With Poet, placed eggs in his meal which killed him via anaphylaxis. (2001)
- Dino Ortolani: Incinerated to death by Johnny Post. Paid off the guards to look the other way. (1997)
- Johnny Post: Tortured and dismembered by the Italians after Ryan admitted he was the one who killed Dino Ortolani. (1997)
- Julio Martinez: Killed by Jefferson Keane. Arranged for him to kill Keane but backfired. (1997)
- Preston Nathan: Strangled to death by Cyril O'Reily. Death ordered from Oz. (1998)
- William Cudney: Stabbed in the neck by Yuri Kosygin. Ordered his death as a hit. (1999)
- Hamid Khan: Accidentally killed during boxing tournament by Cyril O'Reily. Egged on his brother with thoughts of their father. (2000)
- Nikolai Stanislofsky: Electrocuted with a hair dryer plugged in during a bath by Claire Howell. Ordered his death. (2000)
- Nate Shemin: Diced apart by Chris Keller. Conspired with Keller to kill him. (2000)
- Raymond "Mondo" Browne: Stabbed to death by Chris Keller. Conspired with Keller to kill him. (2000)
- Li Chen: Stabbed twice in the heart by Cyril O'Reily for allegedly planning to rape Ryan's mother. (2002)
- Jia Kenmin: Bludgeoned to death by correction officers on Tom Robinson's orders for alledgedly badmouthing the guards which Ryan personally made up. (2002)
- Peter Schibetta: Murdered for allegedly betraying the Italians which Ryan personally made up. (2003)
- Jefferson Keane: Executed by lethal injection due to him killing Julio Martinez. (1997)
- Andrew Schillinger: Died of a drug overdose with drugs supplied by Len Lopresti on Vernon's orders by circumstance arranged by Ryan O'Reily, Chris Keller & Tobias Beecher. (1999)
- Simon Adebisi: Stabbed in the back by Kareem Said. Conspired with Keller to have him killed and overthrow his rule in Em City. (2000)
- Unnamed CO: Killed in a gas explosion caused by Ryan neglecting to turn the gas off. (2001)