|Minor Character: Miami|
|Occupation|| County supervisor|
|Pathology||Corrupt City Official|
|Portrayed By||Ed Begley, Jr.|
|First Appearance||A Grizzly Murder|
O'Shay is elected county supervisor of District 30 and eventually uses his influence for his own personal gain. In 2005, he used his influence to get the casino bill passed and has Doug Lansing assigned to the Indian Legislative Board. Doug Lansing passes O'Shay the profits of the casinos run by Reggie Veston through a courier, a stripper named Anna Sivarro, whom O'Shay convinces to work for him by promising to support her son with some of the profits. Anna Sivarro introduces him to a fellow stripper named Tess Gowan, who also worked as a prostitute. O'Shay became one of her clients and O'Shay even sent Tess to Reggie as a gift, which he accepted and hoped to use as leverage on him one day.
A Grizzly MurderEdit
Anna is later sent to O'Shay, to take Tess' place after she is raped and killed, but Lieutenant Horatio Caine arrives to stop them and arrests O'Shay for solicitation. O'Shay uses his connections to make the charges disappear and is confronted by Caine on his way out.
After this he learns that Tess' black book is left in Anna's possession and tries to get Anna to hand it over to him. When she refuses, O'Shay just keeps pressuring her because of Reggie Veston's name in it. When Doug is murdered, Lieutenant Caine questions him personally where O'Shay implicates Anna. With his connection dead, O'Shay hires Louis Sullivan to steal Tess' black book from Anna's house and to send copies of some pages from the book, including the one with Reggie's name on it, to him. O'Shay then sends that page to Reggie as leverage to have him be Doug's replacement in funneling the money to him. He later learns that his plan backfired when he learns Reggie's wife, Adrienne, found the page first and killed Reggie in retribution for cheating on her. O'Shay is horrified that he can't get anymore money from the casinos and is forced to abandon the casino skimming scam.
At an unknown point he left his position as supervisor and got a job as an inspector at Tallahassee. He eventually returned to Miami to accept a job running the mayor's Civilian Oversight Panel keeping his title of inspector. He eventually ends up in the pocket of a local businessman, Diego Navarro.
Look Who's TauntingEdit
When the Crime Lab run by Lieutenant Caine gets a warrant for the Navarro's son's house based on suture patterns on a murder victim's knee Esteban did, matching sutures the killer used, Diego tells him to quash it. To this end, O'Shay gets a writ stopping the search by paying one of Esteban's attending physicians to say he sutured the victim's leg, not Esteban. When the police find another victim who is alive, O'Shay intimidates the State's Attorney not to prosecute Esteban for his crimes.
O'Shay reappears when the CSIs are investigating the murder of a Mexican Chief of Police's husband by the Mala Noche. He asserts to CSI Duquesne that they have no jurisdiction to investigate this case and she counters that if Memmo Fierro is calling shot from inside then it is in their jurisdiction. She then tells him the bomb has a connection to an ATF facility whose manage is in Miami, O'Shay tells her that the one who gave them their hummers, Hank Craddock, is a member of his board and won't be happy about this. O'Shay has Craddock cut the power to Duquesne's hummer remotely just when an officer is killed by the a Mala Noche hitman. When Duquesne confronts him he asserts the case wasn't in their jurisdiction yet and she warns him that if Craddock messes with her car again she will arrest him for obstruction. O'Shay tracks down CSI Walter Simmons and offers him a job, be his mole on Horatio's team.
When another one of Esteban's victims washes up on the beach, O'Shay starts calling Walter for updates on the case. Walter and O'Shay eventually meet up to discuss some developments on the case involving a break-in at the victims' parents house. Walter tells him that blood evidence at the scene that could exonerate Esteban was contaminated and that the only shot Esteban has is if they get the answering machine the thief stole. O'Shay relays this information to Diego and when Esteban is arrested, Diego provides the answering machine with his attorney present. O'Shay thanks Walter for his cooperation and tells Caine to apologize to the family publicly to save his job. Caine then reveals O'Shay has been set-up, as Walter is a double agent working for Caine and O'Shay leaves in frustration.