Thomas DeSimone - Biography - Criminal Career

Criminal Career

DeSimone was introduced to the Vario Crew in 1965. Henry Hill said in Wiseguy, "Jimmy came by the cab stand one day with a skinny kid who was wearing a wiseguy suit and a pencil mustache. It was Tommy DeSimone. He was one of those kids who looked younger than he was just because he was trying to look older. Jimmy had been a friend of Tommy's family for years, and wanted me to watch out for Tommy and to teach him the cigarette business–help make him a few bucks."

DeSimone worked under Mafia capo Paul Vario with Jimmy Burke, Henry Hill and more. DeSimone was involved in truck hijackings, dealing and fencing of stolen property, extortion, fraud and murder.

DeSimone was infamous for his violent temper: His sister was quoted saying "Tommy's teenage years revolved around boxing, lifting weights, smoking cigarettes, and beating the shit out of a punching bag he kept in a spare room. He had a short fuse, and an animalistic appetite. He would drink almost a gallon of whole milk a day. His only other childhood hobby was collecting different kinds of pocket knives he kept in an old cigar box under his bed." While playing pinochle with Joseph Iannuzzi and Agro, he would throw darts at the other players when he started losing. Henry Hill's ex-wife Karen said in Nicholas Pileggi's book Wiseguy, "Tommy DeSimone always drove around in a brand-new car and wore expensive clothes, and he and Angela lived in a two-room tenement slum," while Hill described DeSimone and Burke by saying, "It didn't take anything for these guys to kill you. They liked it. They would sit around drinking booze and talk about their favorite hits. They enjoyed talking about them." An ex-police detective named Frank Santarsola said "It gave him enjoyment to break somebody's wrist, murder somebody, beating someone with a bat." Hill later described DeSimone as a "pure psychopath" and "Tommy was fucking loose horse, a fucking homicidal maniac and was always strung out on coke constantly." Hill suggested that DeSimone had something to prove because his older brother Anthony had become an informant and was allegedly murdered by the Gambino crime family for that.

During the 1960s, DeSimone and fellow associates Henry Hill, Joey Allegro, and Stanley Diamond would go on regular hijackings. While hijacking, DeSimone would always carry his gun in a brown paper bag. "Walking down the street, he looked like he was bringing you a sandwich instead of a .38." Hill said.

DeSimone committed what is believed to have been his first murder on March 15, 1968. He was walking down the street with Hill when DeSimone spotted Howard Goldstein, a passing pedestrian, unknown to either gangster. Hill recalls DeSimone turning to him and saying, "Hey Henry, watch this." DeSimone yelled, "Hey cocksucker!" and pulled out a .38 caliber pistol, and shot and killed Goldstein. Hill exclaimed, "That was cold-blooded, Tommy!" DeSimone replied, "Well, I'm a mean cat."