O'Leary in 1997
O'Leary in 2007
|Portrayed by||Gordon Clapp|
Daniel O'Leary was a officer of the Philadelphia Police Department in the 1980's and 1990's. O'Leary arrested known stick-up man Pete Doyle in 1985. After Pete's release in 1997, O'Leary murdered Pete after a botched attempt to trick Pete into robbing an armored car for him.
O'Leary, who patrolled North Philly in the 1980's, had a reputation as an aggressive officer, giving suspects a "tour of the city", which involved driving them out to the river, and beating them with his nightstick. O'Leary also harbored a resentment for Pete Doyle, often seeing him flashing stolen money. O'Leary finally arrested Pete in 1985 just after robbing a check-cashing store in North Kensington, when O'Leary caught him with the money and a .38 Smith and Wesson.
Pete was given a twenty year sentence, serving twelve before being released for good behavior. O'Leary wasted little time in following Pete and harassing him at his job at a bar. O'Leary goaded Pete in front of his son, Petey Jr., but the elder Pete didn't rise to it. O'Leary tried to get Robbery to investigate Pete, but they had no reason to.
O'Leary followed Pete to an Alcoholics Anonymous meeting, where he saw Pete with his old partner, Tommy Connell, wearing a .38. Though O'Leary was eager to lock up Pete again, he wanted him on a felony, rather than a gun charge, and kept watching.
In the end, however, it was Pete who came to O'Leary, telling him of a plan of Tommy's, with Petey Jr.'s help, to rob an armored car.
Pete offered O'Leary his full co-operation as an information in return for his son being left out of it. Pete agreed to wear a microphone and wire and go along with the heist. At the right time, Pete would say "I think we hit the jackpot", signaling the police to come in and arrest Tommy.
No one else knew about the plan, however. O'Leary was supposed to to go his Lieutenant about it, but decided not to. O'Leary was being pressured towards forced retirement, as his violent tactics weren't condoned by the Department anymore. Seeing nothing in future but a meager pension and a lifetime of debt, O'Leary had decided to trick Pete into robbing the armored car, then keeping the money for himself. Pete, however, realizing that help would never come, and instructed the driver to hit the panic button, then he and Tommy fled.
Pete caught up with O'Leary and demanded to know where he'd been. When he mentioend that Petey Jr.'s stepfather Bernie Murphy was the driver, O'Leary realized Pete had been recognized, which would lead back to him. He immediately pulled out his gun and took Pete's .38.
While O'Leary forced Pete to his knees, Pete said he felt sorry for the man and defiantly told his nemesis that he'd taken his second chance and got it right. "I'm a good man," Pete said. "What are you?" Without a word, O'Leary shot Pete though the heart with his own gun, killing him, then took the wire off Pete's body and left.
Eleven years later, after Pete's hand was discovered in petty crook Manny Hernandez's freezer, Pete's murder was investigated. After learning about the incident in the bar from Petey Jr., the now divorced and retired O'Leary was questioned by Lieutenant John Stillman and Detective Kat Miller. O'Leary freely told them about following Pete and told them about seeing him with a gun at the AA meeting, which led to Tommy being questioned.
After learning of the heist, and hearing from Bernie what Pete had said there, Homicide detectives deduced Pete had been an information. Detective Nick Vera discovered a microphone and wire signed out by O'Leary the day of the robbery. The equipment had been thrown away years ago, but Detective Lilly Rush pointed out that O'Leary didn't know that.
O'Leary was brough in again with Stillman and Detective Will Jeffries bluffing him, telling him they had his DNA and fingerprints on it. Though skeptical at first, O'Leary eventually fell for their ruse and told them the truth about sending Pete into the robbery. "What was he gonna do?" O'Leary asked, glibly. "Call the cops?"
O'Leary was arrested, as was Tommy, and Petey Jr. finally learned the truth about his father.