“Jimmy came by the cabstand one day with a skinny kid who was wearing a wiseguy suit and a pencil mustache,” it reads in Nicholas Pileggi’s Wise Guy. “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 he wanted me to watch out for Tommy and to teach him the cigarette business – help him make a few bucks. With Tommy helping me, pretty soon we’re making $300, $400 a day. We sold hundreds of cartons at construction sites and garment factories. We sold them at the Sanitation Department garages and at the subway and bus depot. This was around 1965, and the city wasn’t taking it very seriously.”

Henry Hill says Tommy committed his first murder when he was 17 in 1968. DeSimone killed a random stranger named Howard Goldstein as he walked down the street. According to Wise Guy, Henry Hill said to the budding sociopath, “That was cold-blooded, Tommy!” DeSimone explained “Well, I’m a mean cat.”

DeSimone had a hair-trigger temper. One of his sisters claimed “Tommy’s teenage years revolved around boxing, lifting weights, smoking cigarettes, and beating 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.”

Tommy carried his gun in a brown paper bag on hijackings. He carried neighborhood talent through the ropes. “I remember how proud Tommy DeSimone was when he brought Jimmy’s kid, Frankie, on his first hit. Frankie must have been sixteen or seventeen when Tommy took him on the hit, and Tommy said the kid held up great. Jimmy walked around real proud. You’d have thought the kid had won a medal,” it says in Wise Guy, on page 127 of the paperback edition.

Pileggi quotes Hill going through a full rap sheet on Tommy D. Hill fingered Tommy in hijackings, robberies, blackmail, explosives, insurance fraud, and murder, something Tommy did like he was wired that way. For one job,Tommy was supposed to lean on a warehouse foreman named Stanley Diamond, but DeSimone wound up killing him. Hill said DeSimone strangled Dominick “Remo” Cersani, pretty much because Jimmy Burke told him to.

“Jimmy once killed his best friend, Remo, because he found out that Remo set up one of his cigarette loads for a pinch … Remo was dead within a week, he didn’t have a clue what was coming to him,” it says in Wise Guy. “I remember the night. We were all playing cards at Robert’s when Jimmy said to Remo, ‘Let’s take a ride.’ He motioned to Tommy and another guy to come along. Remo got in the front seat and Tommy and Jimmy got in the rear. When they got to a quiet area, Tommy used a piano wire. Remo put up some fight. He kicked and swung and shit all over himself before he died.” Remo is supposed to be buried next to the bocce court behind Robert’s Lounge now.