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 Franchettis 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.