Jackie followed a strict code of morals. Chief among his beliefs was a trust in those who earned it and a fierce loyalty to family and allies. Early in the series, his main love interest was his childhood friend Jenny Romano. He later developed a romance with Sara Pezzini after the birth of their daughter, Hope Pezzini. The son of notorious Mob associate Danny Estacado and an unnamed prostitute, Jackie was taken in by Saint Gerald's Orphanage where he was frequently abused by the orderlies. Despite his antisocial nature even as a boy, Jackie protected his friend Jenny from their cruel treatment. At the age of six, Jackie was adopted by upcoming Mob boss Frankie "Kill-The-Children-Too" Franchetti, claiming to be his uncle. He only did so after being persuaded by Sonatine of the Brotherhood of Darkness that bringing Jackie into his inner circle would make Frankie powerful. Life in the Mob provided Jackie both with a home as well as a sense of safety and family, but also made him more violent and prone to illegal activity. Losing his virginity at age fourteen to a female officer during interrogation, he disregarded the law and developed a sex habit. Making his first hit at age sixteen, Jackie soon became Frankie's chief enforcer; skyrocketing the Franchetti's into one of the top Mob families in New York City and fulfilling Sonatine's prophecy. Living a playboy lifestyle, Jackie would often visit Jenny's club to keep in touch. Both the Angelus and Sonatine kept vigil over the course of Jackie's life; both of them waiting for him to manifest the Darkness - the Brotherhood wishing to exploit his power for their own ends while the Angelus wished only to annihilate the wielder while at his most vulnerable. Jackie was also being watched by followers of the Church of the Angelus which had infiltrated various criminal operations in opposition to Franchetti's. Among them was Regis Tyne, a Mob accountant who would associate with Jackie and attempt to assassinate him over a decade later. When he turned 21, his dark powers awakened, and he learned of his evil heritage. Jackie spent much of his time escaping from or fighting the Angelus, Sonatine, and the Brotherhood of the Darkness. Jackie tried to quit the mob, but Frankie kidnapped and killed Jenny, a childhood friend of Jackie's. Jackie, in a warehouse showdown with Franchetti's crew, blew up the warehouse,