20 Celebrities With (Alleged) Ties To The Mafia

The glamorous world of Hollywood, known for its sparkle and glamour, has a hidden, murky side that occasionally intersects with the shady underworld of the Mafia, a realm of shadows and hushed conversations. For years, tales have been passed around about the ties between prominent entertainers and influential crime families. These stories frequently blur the boundaries between friendship, business deals, and something more ominous, perpetuating a mystique that continues to captivate the public. From renowned singers to esteemed actors, the roster of celebrities rumored to have associations with organized crime is longer than one might expect and brims with intriguing tales.

The suggested relationships span from casual friendships formed in the nightclubs and gambling dens of a past time, to direct and at times questionable ties. For some performers, mingling with actual mob figures was a form of method acting, enhancing their on-screen portrayals of tough characters and gangsters. For others, these connections were simply a matter of circumstance; growing up in areas controlled by the mob or becoming entangled in businesses financed by mysterious individuals. Regardless of the cause, these tales provide an intriguing look into a concealed history where Hollywood’s glamorous film industry intertwined with the harsh reality of organized crime.

Frank Sinatra

Frank Sinatra’s name is almost as closely linked with the Rat Pack as it is with rumors of Mafia ties. The renowned singer was known to have close associations with influential mobsters like Sam Giancana, Lucky Luciano, and Bugsy Siegel, as detailed extensively in his FBI file. Many of these relationships were developed in the nightclubs and casinos controlled by the mafia, where Sinatra often performed. It’s been suggested that these powerful connections aided him in securing performances and maneuvering through the competitive entertainment industry.

For almost five decades, the FBI closely monitored Frank Sinatra’s activities, delving into aspects ranging from his political connections to accusations of extortion. One enduring rumor suggests that Sinatra served as a liaison between Chicago crime boss Sam Giancana and the Kennedy family during John F. Kennedy’s election campaign. Despite repeated denials of any misconduct, Sinatra’s attendance at the notorious 1946 Havana Conference – a gathering of prominent American Mafia figures – added further fuel to the speculation that surrounded him throughout his career.

James Caan

James Caan’s performance as Sonny Corleone in ‘The Godfather’ was so realistic that it seemed more than just acting. In fact, during the filming, Caan was friendly with Carmine “The Snake” Persico, a significant figure in the Colombo crime family. His bond with Andrew “Andy Mush” Russo, the boss of the Colombo family, was so strong that Russo became the godfather to Scott, Caan’s son. When Russo was apprehended in 2011, Caan went as far as writing a letter to the court to offer bail money for him.

In addition to being ordinary friendships, it was revealed that Robert De Niro’s co-star in ‘The Godfather’, James Caan, had deeper ties with the mob. Sammy “The Bull” Gravano, a former Gambino underboss, asserted that Caan was connected to the Colombo family and needed approval from boss Joe Colombo before accepting the role in ‘The Godfather’. Furthermore, there were accusations that Caan once requested a mob associate to physically intimidate actor Joe Pesci due to an overdue hotel bill. However, Caan’s representatives have refuted these claims.

George Raft

Prior to numerous other actors being associated with organized crime, George Raft set the standard as the first Hollywood’s portrayal of a gangster. Born and raised in a rough New York neighborhood, he was companions with future mob leaders such as Bugsy Siegel and Owney Madden during his childhood. This upbringing infused his on-screen characterization of a criminal with an undeniable authenticity that reportedly inspired actual gangsters to adopt his mannerisms and style. Raft’s bond with Siegel was particularly noteworthy, as the infamous mobster resided at Raft’s Hollywood residence for a spell.

Raft’s connections extended beyond his film career, as he often promoted mafia-controlled casinos, luring high-stakes gamblers to venues like the Sands in Las Vegas and the Capri Hotel in Cuba. His association with the underworld ultimately led to him being barred from entering Britain in 1966 due to his criminal connections. Although he maintained that these individuals were merely acquaintances, his career was indelibly linked to the world of organized crime.

Lenny Montana

In my perspective, playing the intimidating character Luca Brasi in “The Godfather” by Lenny Montana was more like life mirroring art. Before delving into acting, Lenny Montana was indeed a professional wrestler and a real-life enforcer for the Colombo crime family. Standing tall at an impressive six feet six inches, he fit perfectly for his role. His duties with the mob ranged from setting fires to providing personal protection for senior members of the family.

Almost by chance, Montana found himself cast in the legendary movie. He was there as a bodyguard for a Colombo family member on set when director Francis Ford Coppola noticed him and believed he’d be ideal for the Brasi role. Apparently, Montana was so apprehensive about acting alongside Marlon Brando that he frequently muddled his lines during practice sessions. Charmingly nervous as it turned out to be, this trait of Montana’s was cherished by Coppola and used to great effect in the final cut, resulting in one of the most impactful scenes in the film.

Tony Sirico

As a dedicated admirer, I can’t help but reflect on Tony Sirico, renowned for his portrayal of Paulie “Walnuts” Gualtieri in the iconic series ‘The Sopranos’. Before he graced our screens with his unforgettable performance, Tony had a fascinating backstory entwined with organized crime. Raised in Brooklyn, he found himself in the orbit of the Colombo crime family, and his past is marked by a long list of legal troubles that resulted in multiple arrests. Convicted for various offenses such as robbery and felony weapon possession, he even spent time behind bars serving his sentences.

During his final stint in prison, Sirico found his love for acting inspired by a performance put on by a troupe of former inmates. His own life experiences undoubtedly added an authentic touch to his portrayal of the faithful yet eccentric mobster. He frequently stressed that his prerequisite for playing Paulie Walnuts was ensuring the character would never betray, a reflection of the code he knew from his earlier life.

Gianni Russo

Giuseppe (Gianni) Russo is mainly recognized for portraying Carlo Rizzi, the abusive spouse of Connie Corleone in ‘The Godfather’. Yet, his real-life tale has been no less captivating, with rumors surrounding him and the underworld. In fact, Russo himself admitted to having ties with various crime syndicates and serving under the notorious gangster Frank Costello during his youth.

Over the years, he has made some remarkable statements, such as suggesting that the Gambino crime family played a part in him landing his role in ‘The Godfather’. Furthermore, according to Russo, he served as an intermediary between Paramount Studios and Joe Colombo Sr., the head of the Colombo family, during the movie’s production. Although it can be challenging to confirm these stories, they paint a vivid picture of a life that straddled the line between Hollywood and the Mafia, teetering on the edge.

Robert De Niro

Robert De Niro is renowned for creating an illustrious film career by portraying mobsters in movies such as ‘Goodfellas’ and ‘Casino’. To infuse authenticity into his performances, it’s said that he spent time with genuine members of criminal organizations to gain insight. For the comedy ‘Analyze This’, accounts suggest that he interacted with Anthony “Fat Andy” Ruggiano, a Gambino crime family member, for character research.

In my perspective as a devoted fan, Robert De Niro’s unwavering commitment to his craft has often led him into the company of individuals associated with the Mafia, though he himself has never confirmed any familial ties. For instance, during the filming of ‘Analyze This,’ an associate of the Gambino family reportedly served as an extra and introduced De Niro to Ruggiano. Though these interactions were brief, they underscore De Niro’s remarkable efforts in delivering his iconic portrayals of gangsters.

Al Pacino

Al Pacino, known for his portrayal of Michael Corleone in ‘The Godfather’ trilogy, even had interactions with real-life gangsters to ready himself for this legendary character. While making the initial film, Pacino and other actors were invited to a gathering at the residence of a prominent figure from the Genovese crime family. This encounter offered him a genuine glimpse into the life he was set to depict in the movie.

The invitation for the project arrived via another actor who had personal connections with a criminal organization, specifically the mob. Initially, Al Pacino and director Francis Ford Coppola showed reluctance to work with genuine criminals. However, these encounters provided a more profound insight into their characters. Pacino’s casual acquaintanceship with the Genovese family during research sessions serves as an intriguing side note in the creation of one of cinema’s most iconic films.

Joe Pesci

Joe Pesci gained fame for his depictions of intense and hardened mob figures, with his most notable role being Tommy DeVito in ‘Goodfellas’, which earned him an Oscar. Born and raised in a working-class community in New Jersey, Pesci’s background mirrored the characters he would portray later on. He had childhood ties to Robert Bisaccia, a notable figure in the American Mafia.

Pesci’s neckties, on the other hand, appear more rooted in his background and friendships than in any explicit participation in criminal acts. Intriguingly, it was once suggested that fellow actor James Caan employed mobsters to attack Pesci over an unpaid hotel bill. Despite their differences in the past, they have since made up. This tale only serves to illustrate further the blurred lines between tough guys on screen and their off-screen counterparts in the criminal world.

Jerry Orbach

Prior to his portrayal as the witty detective Lennie Briscoe on ‘Law & Order’, Jerry Orbach shared an intriguing and affable bond with a well-known mobster. In 1971, Orbach brought to life a character inspired by the real-life mobster “Crazy Joey” Gallo in the comedy ‘The Gang That Couldn’t Shoot Straight’. However, it seemed that Gallo took offense to this portrayal and even arranged a meeting with the actor.

Rather unexpectedly, instead of enemies, the two men developed a strong friendship. This bond was so intimate that Orbach and his wife were present when Gallo was murdered in 1972 at Umberto’s Clam House in Little Italy. It’s said that Orbach witnessed the shooting but chose not to collaborate with law enforcement, keeping the details of what he saw on that fateful night a secret until his death.

Michael Squicciarini

As “Big Mike” Squicciarini, I might say, “Although my character, Frank Cippolina, was only a minor player in ‘The Sopranos’, my real-life involvement in the criminal world was much more significant. I’ve got a history as a debt collector and an associate of New Jersey’s DeCavalcante crime family, which served as part of the inspiration for the show. My criminal record even includes a conviction for aggravated assault.

In 2001, following his passing due to natural causes, Squicciarini was later connected posthumously to the 1992 murder of a drug dealer. Authorities accused him of setting up the victim’s visit to a nightclub where he was fatally shot by a DeCavalcante boss. Witnesses claimed they recognized Squicciarini from his role on “The Sopranos”, tying the TV mob character to a real-life crime involving a mob assassination.

Tony Darrow

Actor Tony Darrow, also known as Anthony Borgese, from ‘The Sopranos’, has ties to organized crime in reality as well as fiction. In the series, he portrayed Larry Boy Barese, a capo within the imaginary DiMeo crime family. Remarkably, in 2011, Borgese admitted guilt for his involvement in an actual extortion scheme masterminded by the Gambino crime family.

The situation revolved around someone trying to recover a debt by using violent intimidation. Instead of facing a potential lengthy jail term, Borgese opted to collaborate and went as far as making a public service announcement against the mafia. This collaboration resulted in a less stringent sentence of home confinement for him. His tale serves as a chilling example of how the boundaries between portraying a gangster on screen and being entangled with them in real life can become unsettlingly indistinct.

Alex Rocco

Alex Rocco, famous for his portrayal of Moe Greene, the casino owner in ‘The Godfather’, had ties to Boston’s Winter Hill Gang in his past. Prior to his acting career, he went by Alexander Petricone and was deeply entrenched in Boston’s criminal network. He was once implicated in a gang-related homicide, but the accusations were eventually dismissed.

Rocco chose to abandon his life of crime, recognizing it as a cul-de-sac, and instead shifted gears by relocating to California and adopting a new identity to pursue an acting career. His real-life experiences lent an unmistakable air of authenticity to his portrayal of the rebellious casino boss, making Moe Greene one of the most indelible characters in that timeless film.

Steven Seagal

Steven Seagal, renowned action star, is reportedly linked to organized crime in a more intricate manner, with accusations of extortion being at the heart of these claims. In the early 2000s, Seagal found himself enmeshed in a federal probe concerning the Gambino criminal family. His ex-business partner, producer Julius Nasso, was charged for allegedly collaborating with the mob to demand money from Seagal through extortion tactics.

Prosecutors claimed that Nasso and associates from the Gambino family pressured Seagal to carry on collaborating with Nasso and hand over a percentage of his film earnings to them. In court, Seagal testified about intimidating incidents involving mobsters who demanded money and threatened him. This case offered an uncommon view into the more sinister aspects of Hollywood business transactions.

Mickey Rourke

Mickey Rourke’s tough persona on screen and rebellious image aren’t mere pretenses; he’s openly discussed his connections with individuals from the criminal underworld. Notably, he was friendly with a Hells Angels member who eventually became president of the New York City chapter. It’s also been reported that his acquaintances stretch to members of organized crime families.

As a follower, I find myself deeply connected to these characters, not just because of their on-screen presence, but due to a strong sense of loyalty and an appreciation for the street-level code of honor they embody. Time and again, I’ve stood by my friendships with these individuals, expressing that their unwavering loyalty towards me is something I highly value. These relationships, while not always met with approval, are integral to the intricate character that makes up the renowned actor, Rourke.

Lillo Brancato Jr.

Lillo Brancato Jr., recognized for his performances in ‘A Bronx Tale’ and as a young gangster in ‘The Sopranos’, experienced a significant setback in his acting career when he became entangled in criminal activities. In 2005, a burglary incident, which turned out to be unsuccessful, led to the fatal shooting of an off-duty police officer, marking a tragic turn in Brancato’s life.

Although he was found not guilty of murder, he was found guilty of attempted burglary and served time in prison. His story serves as a warning of a gifted actor whose personal life became chaotic, merging the criminal underworlds he depicted on screen with real-life turmoil. Since his release, he has openly discussed his struggles and his attempts to reform.

Robert Evans

Robert Evans, the renowned Hollywood producer famous for films like ‘The Godfather’ and ‘Chinatown’, was rumored to have associations with criminal organizations. These links surfaced during the probe into the murder of theater producer Roy Radin, a case that gained notoriety as the “Cotton Club murder.

Evans found himself implicated in the case due to his role in funding the movie ‘The Cotton Club’. Although he was never officially indicted, he was summoned to testify and chose to invoke the Fifth Amendment to prevent self-incrimination. This incident brought to light the frequently murky realm of film financing and the potentially risky individuals who might be part of it.

Elizabeth Hurley

Elizabeth Hurley, an English actress and producer, was romantically involved with Dominic “Donnie Shacks” Montemarano, a known mob figure. In the early 2000s, reports suggest that she had a relationship with Montemarano, who was a convicted enforcer and capo in the Colombo crime family. The two were frequently spotted together in public.

It’s reported that they crossed paths on the film set of ‘Mickey Blue Eyes’, a mob comedy produced by Hurley. At that point, Montemarano was under FBI investigation due to rumors about his part in a college football betting scandal. Their unusual collaboration resulted in many news headlines and unexpectedly added Montemarano’s name to the list of celebrities suspected of having ties to the criminal underworld.

Liza Minnelli

It’s rumored that Liza Minnelli, the renowned singer and actress, had links to the underworld primarily through her romantic relationships. Specifically, she is said to have dated Gianni Russo, an actor from ‘The Godfather’, who has openly discussed his supposed deep connections with organized crime networks. Russo himself has suggested that these criminal connections played a significant role in both his professional success and his social circle.

Russo alleged that their relationship was a rapid and passionate one, potentially linking the esteemed entertainer to the criminal underworld due to her connections with him. Though Minnelli herself has not been implicated in any illegal activities, her rumored romance with Russo further complicates the tangled network of relationships between Hollywood celebrities and organized crime figures.

Wayne Newton

In the 1980s, it was claimed that Wayne Newton, known as “Mr. Las Vegas,” found himself in a controversial situation involving alleged ties to organized crime. Rumors surfaced suggesting that his shared ownership of the Aladdin Hotel was being used as a cover for mafia activities. The accusations implied that the hotel served as a means for criminal figures to gain financial advantages, with Newton’s knowledge and possible complicity.

The accusations sparked an intense investigation and a lawsuit for defamation that Newton filed against a television station over their coverage. Despite strongly refuting the claims, he worked diligently to prove his innocence. This incident brought to light the long-standing connections of organized crime with Las Vegas casinos and showed how prominent figures could unwittingly find themselves ensnared in such affairs.

2025-08-16 08:18