The Series begins in New York City, with Jackie Estacado being introduced as he is stalking an undisclosed person for his "Uncle" Frankie Franchetti. The two suspect that this man has been scamming the Franchetti Crime Family and decide on a whim that he would be better off dead. With that, Jackie turns on his red sports car, crushes the man's lower body with the car and then shoot him several times until he's dead.
He then goes to the bar where he meets Jenny Romano and asks for a glass of milk, much to the latter's surprise. He's then seen flirting with some of the girls inside the bar and eventually leaves with one of them, telling her that he can get her a walk-on part in The Simpsons. Whilst he's at his home with the woman, the reader is introduced to Sonatine, who is spying on him through a mystical source, as well as the current wielder of the Angelus, who wants to kill him the moment he gains The Darkness, hoping to end the Estacado family line once and for all.
The next day he meets up with Uncle Frankie, who is in the middle of dealing with some problems he having with some of his competitors. A Frag grenade gets thrown into the room and Jackie saves Don Franchetti by throwing Mo on top of it. He apologizes to the dying Mo, who tells Jackie not to worry about it and admits that he had betrayed the Franchetti Family. Later when he is seen loading his gun when, precisely at midnight, he starts hearing The Darkness for the first time, falling to the ground in intense pain. Two groups are then seen attacking Jackie. The first is the Brotherhood of Darkness and the second one is a group of the Angelus' warriors. The Brotherhood is easily overwhelmed by the latter group, which are eventually killed off by Jackie using the Darkness for the first time. An enforcer from a rival mafia family then enters and attempts to kill Jackie, but the Estacado manages to save himself by summoning his armor around his body and killing the intruder. He later goes to the mansion of Don Marchianni and manages to kill him by summoning Darkness up the toilet.