20 Celebrities With (Alleged) Ties To The Mafia

The glitz and glamour of Hollywood have always had a darker side, a world of shadows and whispers that sometimes intersects with the notorious underworld of the Mafia. For decades, stories have circulated about the connections between famous entertainers and powerful crime families. These tales often blur the lines between friendship, business, and something more sinister, creating a mystique that continues to fascinate the public. From iconic crooners to legendary actors, the list of celebrities with supposed links to organized crime is surprisingly long and filled with intriguing anecdotes.

These alleged relationships range from casual acquaintanceships forged in the nightclubs and casinos of a bygone era to more direct and sometimes troubling associations. For some actors, consorting with real-life mobsters was a form of method acting, a way to bring authenticity to their on-screen portrayals of tough guys and gangsters. For others, the connections were a matter of circumstance, growing up in neighborhoods where the mob held sway or getting involved in businesses bankrolled by shadowy figures. Whatever the reason, these stories offer a compelling glimpse into a hidden history where the dream factory of Hollywood met the reality of organized crime.

Frank Sinatra

Frank Sinatra’s name is almost as synonymous with the Rat Pack as it is with whispered rumors of Mafia connections. The legendary singer’s FBI file was famously extensive, documenting his associations with prominent mob figures like Sam Giancana, Lucky Luciano, and Bugsy Siegel. These relationships were often forged in the mob-controlled nightclubs and casinos where Sinatra frequently performed. It’s said that these powerful friends helped him secure performance gigs and even navigate the cutthroat world of the entertainment industry.

The FBI kept Sinatra under surveillance for nearly five decades, investigating everything from his political friendships to alleged extortion schemes. One of the most persistent rumors is that Sinatra acted as a go-between for the Chicago Outfit boss Sam Giancana and the Kennedy family during John F. Kennedy’s presidential campaign. Despite consistently denying any wrongdoing, Sinatra’s presence at the infamous 1946 Havana Conference, a major meeting of American Mafia leaders, only fueled the speculation that followed him throughout his career.

James Caan

James Caan’s portrayal of the hot-headed Sonny Corleone in ‘The Godfather’ was so convincing that it perhaps wasn’t all acting. During the making of the film, Caan was known to spend time with Carmine “The Snake” Persico, a high-ranking member of the Colombo crime family. His friendship with Colombo family boss Andrew “Andy Mush” Russo was so close that Russo is the godfather to Caan’s son, Scott. When Russo was arrested in 2011, Caan even wrote a letter to the court offering to pay his bail.

These weren’t just casual friendships either. Former Gambino underboss Sammy “The Bull” Gravano claimed that Caan was an associate of the Colombo family and had to get permission from boss Joe Colombo to even take the role in ‘The Godfather’. There were also allegations that Caan once asked a mobster associate to rough up actor Joe Pesci over an unpaid hotel bill, though Caan’s representatives have denied this.

George Raft

Long before many other actors were linked to the mob, George Raft was the original Hollywood gangster. He grew up in a tough New York neighborhood and was childhood friends with future mob bosses Bugsy Siegel and Owney Madden. This background gave his on-screen gangster persona an authenticity that was so convincing, it’s said that real-life mobsters started to emulate his style and mannerisms. His friendship with Siegel was particularly strong, with the notorious gangster even living at Raft’s Hollywood home for a time.

Raft’s connections proved useful beyond the silver screen. He acted as a shill for mob-run casinos, using his celebrity to attract high-rollers to places like the Sands in Las Vegas and the Capri Hotel in Cuba. His underworld ties eventually caught up with him, leading to him being banned from entering Britain in 1966 due to his mob associations. Despite his claims that these figures were just acquaintances, his career was forever intertwined with the world of organized crime.

Lenny Montana

Lenny Montana’s role as the fearsome enforcer Luca Brasi in ‘The Godfather’ was a case of art imitating life. Before he was an actor, Montana was a professional wrestler and an actual enforcer for the Colombo crime family. Standing at an imposing six-foot-six, he was well-suited for the job. His work for the mob included arson and acting as a bodyguard for senior members of the family.

His casting in the iconic film was almost accidental. Montana was on the set as a bodyguard for a Colombo family member when director Francis Ford Coppola spotted him and thought he was perfect for the part of Brasi. Montana was reportedly so nervous about acting alongside Marlon Brando that he kept fumbling his lines during rehearsal. Coppola found this genuine nervousness endearing and incorporated it into the final film, creating one of its most memorable scenes.

Tony Sirico

Tony Sirico, beloved for his role as Paulie “Walnuts” Gualtieri on ‘The Sopranos’, had a well-documented history with organized crime before his acting career took off. Growing up in Brooklyn, he was an associate of the Colombo crime family and had a lengthy rap sheet with numerous arrests. He was convicted of several crimes, including robbery and felony weapon possession, and served time in prison.

It was during his last prison sentence that Sirico discovered his passion for acting after seeing a performance by a group of ex-convicts. His real-life experiences undoubtedly lent an air of authenticity to his portrayal of the loyal but quirky mobster. He often said that his one condition for playing Paulie Walnuts was that the character would never become a “rat” or informant, a testament to the code he was familiar with from his past life.

Gianni Russo

Gianni Russo is best known for playing Carlo Rizzi, the abusive husband of Connie Corleone in ‘The Godfather’. However, his life off-screen has been even more dramatic, with claims of deep connections to the mob. Russo has said he had associations with several crime families and even worked for the legendary mobster Frank Costello as a young man.

He has also made some startling claims over the years, including asserting that the Gambino crime family helped him get his role in ‘The Godfather’. According to Russo, he also acted as a go-between for Paramount Studios and Colombo family boss Joe Colombo Sr. during the film’s production. His stories, while sometimes difficult to verify, paint a picture of a life lived on the edge, deeply enmeshed in the worlds of both Hollywood and the Mafia.

Robert De Niro

Robert De Niro has built a legendary career playing mobsters in films like ‘Goodfellas’ and ‘Casino’. To bring a sense of realism to his roles, he has allegedly spent time with actual members of organized crime. For his part in the comedy ‘Analyze This’, it’s reported that he met with Anthony “Fat Andy” Ruggiano, a member of the Gambino crime family, to research the character.

While De Niro himself has downplayed these associations and there is no evidence he has any direct family ties to the Mafia, his dedication to his craft has led him to interact with figures from that world. An associate of the Gambino family was reportedly an extra on the set of ‘Analyze This’ and introduced the actor to Ruggiano. These encounters, however brief, demonstrate the lengths De Niro has gone to in order to perfect his iconic gangster portrayals.

Al Pacino

Al Pacino, who famously played Michael Corleone in ‘The Godfather’ trilogy, also had encounters with real-life mobsters to prepare for his iconic role. During the production of the first film, Pacino, along with other cast members, attended a dinner party at the home of a high-ranking member of the Genovese crime family. This meeting provided him with a firsthand look into the world he was tasked with portraying on screen.

The invitation came through a fellow actor who had family ties to the mob. While Pacino and director Francis Ford Coppola were initially hesitant to associate with actual criminals, these experiences gave the actors a deeper understanding of the characters they were playing. Pacino’s casual links to the Genovese family through these research-oriented meetings are a fascinating footnote in the making of one of cinema’s greatest films.

Joe Pesci

Joe Pesci is famous for his portrayals of volatile and tough mob characters, most notably his Oscar-winning role as Tommy DeVito in ‘Goodfellas’. Growing up in a working-class neighborhood in New Jersey, Pesci was familiar with the types of characters he would later play. He was childhood friends with Robert Bisaccia, a figure in the American Mafia.

Pesci’s ties, however, seem to be more about his upbringing and friendships than any direct involvement in criminal activities. In a strange twist, it was once alleged that fellow actor James Caan hired mobsters to assault Pesci over an unpaid hotel bill. The two actors have since reconciled, but the story adds another layer to the intersection of Hollywood tough guys and their real-life counterparts.

Jerry Orbach

Before he was known as the wise-cracking detective Lennie Briscoe on ‘Law & Order’, Jerry Orbach had a fascinating and friendly relationship with a notorious mobster. In 1971, Orbach played a character based on the real-life mobster “Crazy Joey” Gallo in the comedy ‘The Gang That Couldn’t Shoot Straight’. Gallo was reportedly not pleased about the portrayal and arranged a meeting with the actor.

Instead of a confrontation, the two men surprisingly became good friends. Their friendship was so close that Orbach and his wife were with Gallo on the night he was murdered in 1972 at Umberto’s Clam House in Little Italy. It’s rumored that Orbach was an eyewitness to the shooting but refused to cooperate with the police, taking the secret of what he saw that night to his grave.

Michael Squicciarini

Michael “Big Mike” Squicciarini was a minor character in ‘The Sopranos’, playing an enforcer named Frank Cippolina. However, his real-life criminal background was far more extensive than his acting credits. Squicciarini was a former debt collector and associate of New Jersey’s DeCavalcante crime family, the real-life organization that partly inspired ‘The Sopranos’. He had a criminal record that included a conviction for aggravated assault.

After his death from natural causes in 2001, Squicciarini was posthumously implicated in the 1992 murder of a drug dealer. Prosecutors alleged that he helped lure the victim to a nightclub where he was shot by a DeCavalcante capo. Witnesses reportedly recognized Squicciarini from his appearance on ‘The Sopranos’, linking the television mobster to a real-life mob hit.

Tony Darrow

Anthony Borgese, who used the stage name Tony Darrow, is another actor from ‘The Sopranos’ with real-life mob connections. He played Larry Boy Barese, a capo in the fictional DiMeo crime family. In 2011, Borgese pleaded guilty to being part of a real-life extortion plot orchestrated by the Gambino crime family.

The case involved an attempt to collect a debt through threats of violence. Rather than face a long prison sentence, Borgese agreed to cooperate and even recorded an anti-mafia public service announcement. This cooperation helped him receive a more lenient sentence of house arrest. His story is a stark reminder that sometimes the lines between playing a mobster on TV and being involved with them in reality can become dangerously blurred.

Alex Rocco

Alex Rocco, known for his role as the Las Vegas casino owner Moe Greene in ‘The Godfather’, had a past that included associations with Boston’s Winter Hill Gang. Before becoming an actor, he was known as Alexander Petricone and was involved in the city’s criminal underworld. He was once arrested in connection with a gang-related murder, although the charges were later dropped.

According to Rocco himself, he decided to leave his life of crime behind after realizing it was a dead-end path. He moved to California and changed his name to pursue acting. His experiences gave his portrayal of the defiant casino boss an undeniable edge of authenticity, making Moe Greene one of the most memorable characters in the classic film.

Steven Seagal

Action star Steven Seagal’s alleged connections to the mob are more complex and involve claims of extortion. In the early 2000s, Seagal became entangled in a federal investigation into the Gambino crime family. His former business partner, producer Julius Nasso, was indicted for conspiring with the mob to extort money from the actor.

According to prosecutors, Nasso and members of the Gambino family threatened Seagal to get him to continue working with Nasso and pay them a portion of his movie earnings. Seagal testified against them in court, detailing intimidating encounters where mobsters demanded money and threatened his life. The case provided a rare public glimpse into the darker side of Hollywood business dealings.

Mickey Rourke

Mickey Rourke’s rebellious image and tough-guy roles are not just an act; he has spoken openly about his friendships with figures from the criminal underworld. He was notably friends with a member of the Hells Angels who later became the president of the New York City chapter. His associations have also reportedly extended to members of organized crime families.

Rourke’s affinity for these characters stems from a sense of loyalty and an understanding of the street-level code of honor. He has often defended his friendships, stating that he values the loyalty he has received from these individuals. These connections, while controversial, are part of the complex persona of the acclaimed actor.

Lillo Brancato Jr.

Lillo Brancato Jr. is best known for his roles in ‘A Bronx Tale’ and as a young mobster in ‘The Sopranos’. His promising acting career took a tragic turn due to his involvement in crime. In 2005, Brancato was involved in a botched burglary that resulted in the death of an off-duty police officer.

While he was acquitted of murder, he was convicted of attempted burglary and sentenced to prison. His case is a cautionary tale of a talented actor whose life spiraled out of control, blurring the lines between the fictional criminal worlds he portrayed and real-life tragedy. Since his release, he has spoken about his struggles and his efforts to turn his life around.

Robert Evans

The legendary Hollywood producer Robert Evans, known for his work on classics like ‘The Godfather’ and ‘Chinatown’, also had alleged ties to the world of organized crime. These connections came to light during the investigation into the murder of theatrical producer Roy Radin, a case that became known as the “Cotton Club murder.”

Evans was linked to the case through his involvement in the financing of the film ‘The Cotton Club’. Although he was never charged, he was called to testify and pleaded the Fifth Amendment to avoid incriminating himself. The scandal shed light on the often-shadowy world of movie financing and the dangerous characters that can sometimes be involved.

Elizabeth Hurley

The English actress and producer Elizabeth Hurley found herself linked to the mob through a romantic relationship. In the early 2000s, she was reportedly dating Dominic “Donnie Shacks” Montemarano, a convicted enforcer and capo in the Colombo crime family. The two were seen together publicly on several occasions.

They are said to have met on the set of the mob comedy ‘Mickey Blue Eyes’, which Hurley produced. At the time, Montemarano was under FBI scrutiny for alleged involvement in a college football betting scandal. Their unlikely pairing generated numerous headlines and added an unexpected name to the list of celebrities with connections to the underworld.

Liza Minnelli

The iconic singer and actress Liza Minnelli’s connection to the mob is said to have come through her romantic life. She reportedly dated Gianni Russo, the actor from ‘The Godfather’ who has claimed to have extensive ties to organized crime. Russo has alleged that his mob connections were instrumental in his career and his social life.

Russo has claimed that their relationship was a whirlwind affair, placing the beloved entertainer in the orbit of the criminal underworld through her association with him. While Minnelli herself has not been accused of any wrongdoing, her reported romance with Russo adds another layer to the intricate web of relationships between Hollywood stars and the mob.

Wayne Newton

Mr. Las Vegas himself, Wayne Newton, faced allegations of mob ties in the 1980s. Reports emerged that accused Newton of using his co-ownership of the Aladdin Hotel as a frontman for the Mafia. The claims suggested that organized crime figures were using the hotel for their own financial benefit with Newton’s knowledge.

The allegations led to a high-profile investigation and a defamation lawsuit filed by Newton against a television network that reported on the story. While he fiercely denied the accusations and ultimately worked to clear his name, the controversy highlighted the deep-rooted history of mob involvement in the Las Vegas casino industry and how even its biggest stars could get caught in the middle.

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