During the 1950s, Litif married an
Irish American woman named Anna (nee Duggan) They had two children, a daughter and a son. Litif made himself a fixture on the handball courts at the L Street Bathhouse, playing all comers for $25 or $50 a game. His reputation as an earner made him popular with South Boston's criminal elite, and at one point police believed he was essentially running the neighborhood gambling rackets, taking in as much as $20,000 a week. In the late 1960s and early 1970s, Litif was considered, in official circles, to be one of the top bookmakers in South Boston. He was one of the few prominent
Lebanese Americans active in
Boston's criminal underworld other than the brothers. Before 1976, when he began associating with the
Winter Hill Gang, little is known about Litif, except that he was the leader of a large-scale sports gambling operation. Partnered with a fellow bookie known as "Joe the Barber," the operation was one of the biggest moneymakers for neighborhood boss
Donald Killeen and his successors. According to former South Boston mob informant
Kevin Weeks, who was then the
bouncer in the Triple O's saloon, Litif became more violent, beginning in the late 1970s. In 1975, he was arrested and convicted for pistol whipping an individual with a
.357 Magnum which he carried in the waistband of his pants and pulled out whenever he had the urge. Eventually, Boston newspapers reported that Litif was suspected of shooting a man named Lip Mongelio six times after an argument, in the alley outside Hap's Lounge, the bar Litif co-owned with fellow bookmaker, James Matera. The doctors at Boston City Hospital were able to save Litif's alleged victim. According to Weeks, Litif had never shot anyone before and began walking toward the police station, intending to turn himself in. However, he was intercepted by Bulger, who calmed him down and drove him home. It was alleged Bulger sent an associate of his to convince Mongelio to not press charges against Litif. According to Weeks, ==The murders of Matera and Conrad==