- "He's the one you really watch out for. The guy who makes his rules subject to change at any moment and for any reason."
- – Jackie Estacado describing O'Malley [src]
|Real World information|
At some point Jackie Estacado slept with O'Malley's wife. O'Malley found them during the act and confronted Jackie, which in response flatten his head.
Hired by Paulie Edit
After realizing that he needs professional help in order to takedown Jackie, Paulie Franchetti visits the Triplets. After explaining who they will need to kill, The Triplets agree with Paulie's offer.
Together with Mindy and Tank they visit Nicky Barrucci and kill him. They then wait for Jackie. Once Jackie visits Barrucci, they confront him and Tank knocks him out by using severed Barrucci's head.
They later tie Jackie to a wall with chains. Jackie makes fun of O'Malley, reminding the last time they met. He then proceeds to break a lamp and unleash the Darkness on the Triplets, killing them in the process.
O'Malley is cold, calculated and a man of few words. He felt deep hate towards Jackie for sleeping with his wife and then flattening his head.