Raised as a hit-man for the Franchetti Family Mob, Jackie's defining quality was his penchant for murder as well as womanizing. Despite his criminal lifestyle, 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.