The Real Story Of Tommy DeSimone — The Psychotic Gangster Behind Joe Pesci’s ‘Goodfellas’ Character
Thomas Anthony DeSimone was one of the most volatile and feared figures in the New York Mafia during the 1960s and 1970s. Born into a family deeply connected to organised crime, DeSimone’s early exposure to the mob world shaped him into a ruthless and unpredictable enforcer. With close ties to the Lucchese crime family, his criminal career saw him involved in notorious heists, brutal murders, and a string of violent outbursts that left even seasoned mobsters unnerved.
Thomas Anthony DeSimone, born on May 24, 1950, in Cambridge, Massachusetts, grew up in a family deeply entrenched in the world of organised crime. His father, also named Thomas DeSimone, was a recognised figure in the underworld, and his brothers Anthony and Robert followed in similar footsteps, becoming associates of the Gambino crime family. Anthony’s fate was grim, being murdered by Thomas Agro in 1979, while Robert’s involvement with the Mafia also shaped his future. DeSimone’s personal life was similarly complicated, with his sister Phyllis involved in a long-term affair with James Burke, a man who would later become one of DeSimone’s most influential criminal mentors.
DeSimone’s early life was marked by a swift immersion into crime, setting him on a path that would ultimately lead to his notorious reputation. At the age of 15, DeSimone was introduced to Paul Vario, a caporegime in the Lucchese crime family. Through Vario, DeSimone met Henry Hill and James "Jimmy the Gent" Burke, two prominent figures in the Lucchese crew. Hill, in particular, recalled his first encounter with the young DeSimone, describing him as "a skinny kid who was wearing a wiseguy suit and a pencil moustache." Despite his youth, DeSimone's desire to belong to the Mafia world was evident from the start.
By the time he was 20, DeSimone was already participating in serious criminal activities, including truck hijackings, fencing stolen goods, and extortion. The mob’s world was brutal, and DeSimone thrived in its violence. He quickly gained a reputation for his unpredictability and short temper. His weapon of choice was a .38-caliber revolver, which he carried inconspicuously in a brown paper bag—something Henry Hill would later note as part of DeSimone’s ability to blend into the everyday surroundings while always being armed.
The Air France Heist
One of DeSimone's early criminal milestones came in 1967, when he participated in the infamous Air France robbery. The heist was a sophisticated operation, targeting a shipment of cash flown from Southeast Asia to New York. Air France was responsible for transporting large amounts of currency to the U.S., often storing these sums temporarily at John F. Kennedy International Airport. The cash was kept in a cement strong room, but lax security allowed DeSimone, Burke, and Hill to walk right in without arousing suspicion.
Robert McMahon, an Air France employee, provided the key tip for the robbery, identifying a window of time when the security guard would be on break. On April 7, 1967, DeSimone and Hill entered the cargo terminal and used a duplicate key to access the room where the money was kept. In less than half an hour, the duo stole $420,000 in cash, without firing a single shot or alerting anyone. The robbery wasn’t discovered until three days later, making it one of the smoothest heists in the mob’s history.
The Air France robbery solidified DeSimone's place within the Lucchese family, marking him as an effective and capable criminal. However, despite his skill in pulling off heists, DeSimone’s violent tendencies often overshadowed his abilities.
The Murder of William Bentvena
Perhaps the most infamous incident that cemented DeSimone’s violent reputation was the murder of William "Billy Batts" Bentvena in 1970. Bentvena, a made member of the Gambino crime family, had just been released from prison and was celebrating his return at a party held at Robert’s Lounge, a bar owned by James Burke. During the festivities, Bentvena made a seemingly innocent remark about DeSimone's former job shining shoes. DeSimone, who was deeply insecure about his lowly past, perceived the comment as an insult.
Two weeks later, DeSimone enacted his revenge. Along with Hill and Burke, he lured Bentvena to a nightclub, where he attacked him with a pistol, savagely beating him to the point where they thought Bentvena was dead. The three men stuffed Bentvena’s body into the trunk of a car and drove off to dispose of it. However, during the journey, they realised that Bentvena was still alive, groaning from the trunk. DeSimone and Burke stopped the car and finished the job, beating Bentvena to death with a tire iron and shovel. The body was initially buried at a dog kennel, but when the property was sold months later, Burke ordered DeSimone and Hill to exhume the remains and dispose of them elsewhere, likely crushing them in a compactor or re-burying them under Robert’s Lounge.
This murder, brutal even by Mafia standards, showcased DeSimone's lethal temper and his willingness to kill for even perceived slights. His violent nature became notorious within mob circles, but it was also a double-edged sword—DeSimone was feared, but his reckless actions put him on a dangerous path.
The Murder of Michael "Spider" Gianco
One of the most chilling examples of DeSimone’s lack of control came during a card game, where Michael "Spider" Gianco, a young bartender, inadvertently insulted him. The initial conflict began when Gianco forgot to bring DeSimone a drink, prompting DeSimone to shoot him in the leg in a fit of anger. The situation could have ended there, but a week later, when Gianco returned to work with his leg in a cast, DeSimone began taunting him again. Gianco, emboldened by Burke’s joking support, told DeSimone to "go fuck [himself]."
The room fell silent, and DeSimone, now humiliated in front of his peers, shot Gianco three times, killing him instantly. Even James Burke, a hardened killer, was stunned by DeSimone’s senseless murder. DeSimone was forced to bury Gianco’s body himself, but it is believed that the remains were moved multiple times and may never be recovered.
Henry Hill, who witnessed these murders, later described DeSimone as a psychopath, a man whose violent tendencies seemed uncontrollable. The incident with Gianco, in particular, highlighted DeSimone’s volatility and inability to tolerate even the slightest perceived disrespect.
The Lufthansa Heist
DeSimone's involvement in the notorious Lufthansa heist, which took place on December 11, 1978, added another major event to his criminal résumé. Organised by James Burke, the heist saw a group of mobsters steal $5.875 million (around $27.4 million today) in cash and jewellery from the Lufthansa cargo terminal at JFK Airport. It was the largest cash robbery in U.S. history at the time, and DeSimone was one of the key participants. The heist itself was carefully planned, with Burke selecting a crew that included DeSimone, Robert McMahon, Angelo Sepe, and several others.
The plan was executed without a hitch, but trouble arose after the heist. Burke, notorious for eliminating anyone who could potentially link him to a crime, began systematically killing those involved in the heist. One of DeSimone’s assignments was to murder Parnell "Stacks" Edwards, who had failed to dispose of the getaway van, leaving it in a location where it was discovered by police. Edwards’ fingerprints were found in the vehicle, leading Burke to order his execution. DeSimone and Sepe tracked Edwards down and shot him multiple times, ensuring his silence.
Disappearance and Death
In the wake of the Lufthansa heist, DeSimone’s life took a dangerous turn. By 1979, his violent outbursts and unsanctioned murders, particularly those of Gambino family associates William Bentvena and Ronald Jerothe, had made him a target. It is believed that the Gambino family sought revenge for these killings, and on January 14, 1979, DeSimone vanished. His wife, Angela, reported him missing after he borrowed $60 from her and failed to return.
Henry Hill, who had turned informant, later revealed that DeSimone had been lured to his death under the pretense that he was going to be "made" in the Lucchese family. Instead, he was executed by Gambino family members, possibly with John Gotti himself involved. While the exact details remain murky, several mob insiders, including Thomas Agro, claimed to have taken part in the killing. Some accounts suggest that DeSimone was tortured before his death as punishment for the murder of Bentvena, a personal friend of Gotti’s.
Despite his short life, DeSimone’s violent reputation left a lasting legacy in Mafia history. His story became widely known through Henry Hill’s memoir Wiseguy and its cinematic adaptation Goodfellas. DeSimone, portrayed by Joe Pesci in the film, was depicted as an erratic, hot-headed killer, a characterisation that aligned closely with the real DeSimone's behaviour. His story serves as a stark example of the violent, unpredictable nature of life in the Mafia, where even those deeply entrenched in the organisation are not immune from retribution.
DeSimone’s disappearance remains unsolved, and his body has never been recovered. It is believed that he was buried in The Hole, a notorious Mafia burial ground near JFK Airport. Today, Thomas DeSimone is remembered as one of the most dangerous figures in New York’s organised crime history, a man whose violent tendencies ultimately led to his own demise.