The True Gangsters Behind Goodfellas: A Dive into the Real-Life Crime Stories

When Goodfellas hit cinemas in 1990, it set a new benchmark for gangster films, with its vivid portrayal of life in the Mafia. Directed by Martin Scorsese, the film’s striking realism derived from its roots in real events. Unlike the operatic narratives of The Godfather or the nostalgic arcs of Once Upon a Time in America, Goodfellas offered an unflinching look into organised crime through the lens of a single gangster, Henry Hill, and his associates in the Lucchese crime family.

This gritty authenticity was thanks to Nicholas Pileggi’s 1986 non-fiction book, Wiseguy, which chronicles Hill’s life and criminal exploits, including the audacious Lufthansa heist of 1978—one of the most significant robberies in American history. The crime involved stealing $5.875 million (equivalent to over $20 million today) in cash and jewels from a vault at New York’s John F. Kennedy International Airport. It remains infamous not only for the sheer scale of the theft but also for the bloodshed that followed.

Henry Hill: The Storyteller of the Underworld

Henry Hill, portrayed by Ray Liotta, serves as both the central character and narrator of Goodfellas. Born in 1943 in Brooklyn to an Irish-American father and a Sicilian-American mother, Hill grew up idolising the Mafia figures in his neighbourhood. By the age of 14, he dropped out of school and began working for Paul Vario, a Lucchese crime family capo.

Starting with errands and collecting cash, Hill quickly became embroiled in arson, credit card fraud, and assaults. Despite his Irish heritage preventing him from becoming a made man, Hill gained the trust of Vario and became a crucial associate of the crew.

Hill’s criminal portfolio expanded during the 1970s, involving truck hijackings, narcotics trafficking, and a point-shaving scheme with the 1978–79 Boston College basketball team. However, it was the Lufthansa heist that cemented his place in mob history. His downfall came in 1980 when he was arrested on drug trafficking charges. Facing prison and fearing for his life after rumours surfaced that his associates planned to kill him, Hill turned informant.

His testimony brought numerous convictions, and he entered the Witness Protection Program, though his continued criminal activities and tendency to reveal his identity led to his expulsion. Despite these risks, Hill survived and died of heart disease in 2012.

James “Jimmy the Gent” Burke: The Ruthless Mastermind

Robert De Niro’s portrayal of Jimmy Conway in Goodfellas was based on James Burke, the architect of the Lufthansa heist. Born in 1931 in New York City, Burke endured a traumatic childhood in foster care, marked by abuse and neglect. By his early twenties, he had found his way into Paul Vario’s crew.

Nicknamed “Jimmy the Gent” for tipping truck drivers during hijackings, Burke was anything but gentle when it came to maintaining control. His violent reputation included gruesome murders, such as the dismemberment of his fiancée’s ex-boyfriend on their wedding day.

Burke’s brilliance as a criminal strategist shone during the Lufthansa heist, but paranoia and greed led him to orchestrate the murders of several accomplices, ensuring they wouldn’t betray him. His criminal empire unravelled following Henry Hill’s cooperation with authorities. Burke was sentenced to 20 years for his role in the Boston College point-shaving scandal and received a life sentence for a prior murder while in prison. He died of lung cancer in 1996.

Karen Hill

Karen Hill — Henry’s wife, played by Lorraine Bracco in the film — was born Karen Friedman in New York City in 1946. Soon after her birth, her family moved to Long Island where she was raised in the Five Towns area.

She first met Henry through mutual friends while she was working at a dental office in New York. The pair’s first meeting — at the Villa Capra, a restaurant owned by notorious mobster “Frankie The Wop” — was a double date involving Paul Vario’s son, Paul Jr. (not Thomas DeSimone, as depicted in the film).

At first, Karen said that the date was disastrous and that Henry even stood her up on her second date, only further lowering her opinion of him. However, following a number of lavish dates after these initial fiascos, the two became a couple.

Karen and Henry eloped to North Carolina in 1965 when she was just 19, but eventually had a large Jewish ceremony back home to appease her parents. Soon after, they had two children, Gregg and Gina, and lived together with Karen’s parents before moving into their own place as Henry’s status rose within Vario’s crew.

But things turned sour when Henry went to prison on extortion charges in the 1970s.

In his memoirs, Henry claims that, during this time, Karen was sleeping with Vario. When Henry faced prison again, on drug charges in 1980, he instead testified for the government, entered the Witness Protection Program, and took Karen and their kids along with him.

Eventually, however, Karen and Henry divorced in 1989, though it was not finalised until 2001.

Since then, she has remarried and lived under an alias due to the exposure from Wiseguy and Goodfellas.

Thomas DeSimone: The Volatile Enforcer

Joe Pesci’s Oscar-winning portrayal of Tommy DeVito in Goodfellas brought to life the chilling volatility of Thomas DeSimone. Born in 1950 in Massachusetts into a Mafia family, DeSimone grew up surrounded by organised crime. Through his sister Phyllis, a mistress of Jimmy Burke, DeSimone joined the Vario crew.

Known for his explosive temper and penchant for violence, DeSimone committed his first murder at 17, shooting a random pedestrian to impress Henry Hill. His most infamous act was the 1970 murder of Billy Batts, a made man in the Gambino family. After Batts insulted DeSimone about his past as a shoeshine boy, DeSimone and Burke brutally killed him and buried his body. This act of defiance against the Gambino family set the stage for DeSimone’s eventual demise.

After his role in the Lufthansa heist, DeSimone continued his violent streak, even killing Parnell “Stacks” Edwards, who had failed to dispose of the heist’s getaway van. In 1979, DeSimone vanished, likely killed by the Gambinos in retaliation for Batts’ murder.

Paul Vario: The Capo of East New York

Paul Vario, reimagined as Paul Cicero in Goodfellas and played by Paul Sorvino, was a towering figure in the Lucchese crime family. Born in 1914, Vario dominated the East New York criminal scene, leveraging his union connections to control operations at JFK Airport.

Vario approved the Lufthansa heist and provided the infrastructure for its execution. However, his ruthlessness extended beyond financial dealings. A notorious story recounts how he ordered an assault on a restaurant staff after a waiter spilled wine on his wife.

Ultimately, Vario’s empire crumbled due to Hill’s testimony. He was convicted of defrauding the government and died of a heart attack in prison in 1988.

Billy Batts: The Gambino Made Man Who Met a Brutal End

Billy Batts, played by Frank Vincent in Goodfellas, was a pivotal figure in both the film’s narrative and the real-life events that inspired it. Born William Bentvena in 1921 in New York City, Batts grew up in the same East Brooklyn neighbourhood as Henry Hill. Like many of his peers, he gravitated toward organised crime and eventually became a trusted associate of the Gambino crime family.

By 1961, Batts had risen to the rank of made man, an elite status within the Mafia reserved for full-blooded Italian-Americans. His rise coincided with the era of John Gotti, another Gambino enforcer, with whom Batts often worked. However, his career came to a halt in 1964 when he was arrested during a drug deal in Bridgeport, Connecticut. Sentenced to six years in prison, Batts left a vacuum in his criminal operations, which were quickly taken over by Jimmy Burke.

Upon Batts’ release from prison in 1970, he sought to reclaim his loansharking business from Burke, but this demand put him in conflict with his successor. Things came to a head during a “welcome home” celebration at Robert’s Lounge, a bar owned by Henry Hill and frequented by the Vario crew. Batts, perhaps emboldened by his status as a made man, made a fatal mistake when he publicly humiliated Thomas DeSimone.

In front of a crowd, Batts joked about DeSimone’s past as a shoeshine boy, saying, “Go home and get your shine box!” DeSimone, already known for his violent temper, was enraged. However, Mafia protocol dictated that killing a made man without permission would incur deadly consequences, so DeSimone and Burke waited for the right opportunity.

Two weeks later, Batts was invited to another gathering at the bar. This time, it was a trap. After getting Batts drunk, Burke and DeSimone launched a brutal attack. DeSimone pistol-whipped Batts until he fell unconscious, while Burke restrained him. Believing him to be dead, the group loaded Batts’ body into the trunk of a car. However, as they drove away, they heard noises from the trunk—Batts was still alive. The group pulled over, and DeSimone and Burke stabbed and beat him to death before burying the body under a dog kennel.

Retribution from the Gambinos

The murder of Billy Batts was a reckless move, one that demonstrated the hubris of Burke and DeSimone. As a made man in the Gambino family, Batts’ death would not go unanswered. While Paul Vario shielded his crew for a time, the murder created tension between the Lucchese and Gambino families.

Ultimately, it was likely Batts’ murder that sealed DeSimone’s fate. According to Henry Hill’s later testimony, DeSimone’s disappearance in 1979 was orchestrated by the Gambino family as revenge. In a grim irony, Paul Vario, DeSimone’s mentor, is believed to have handed him over to the Gambinos, reportedly as punishment for attempting to assault Karen Hill, Henry’s wife and Vario’s mistress.

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