5 Celebrities Rumored to Have Mob Ties

When Marilyn Monroe died in August 1962, speculation about her private life surged. Beyond Hollywood, Monroe mingled with powerful politicians and entertainers, including Frank Sinatra, whose ties to organized crime had long been speculated.

Much of the discussion focused on Sam Giancana, a Chicago Outfit boss and powerful organized crime figure in the 1950s and early 1960s. Giancana had social ties to both Sinatra and people in the Kennedy family circle. Some theories suggest Monroe was connected to an intersection of Hollywood, politics and organized crime. Other sources suggest that Giancana was concerned Monroe might disclose information regarding her relationships with John F. Kennedy and Robert F. Kennedy. These disclosures, some argue, could have jeopardized the Kennedy family’s reputation.

Stories circulated that Monroe’s phone calls had been monitored and that sensitive recordings existed. Years later, actor Gianni Russo claimed Monroe had been killed because powerful individuals feared what she knew. None of the allegations were ever proven, but they helped turn Monroe’s death into one of America’s most enduring conspiracy stories.

“Both Frank Sinatra and Marilyn Monroe are iconic cultural figures, so their connections to organized crime (and the lack thereof) remain interesting details in their lives,” says Zach Jensen, content development manager at The Mob Museum. “And both…are surrounded by legend.”

Sinatra’s relationships with Giancana and other alleged mobsters were widely reported throughout the mid-20th century. The FBI even tracked Sinatra for years due to those associations and concerns over his political influence. Many historians argue Sinatra’s nightclub career placed him in environments where entertainment and crime routinely mixed. “In the first half of the 20th century, organized crime figures controlled the nightclub scene and worked with the entertainment industry to book acts,” Jensen says. “This extended to Las Vegas casinos, too.”

These relationships, however, often reflected proximity more than criminal involvement. Still, Sinatra’s image became inseparable from the mythology. His tailored suits, Las Vegas lifestyle and friendships with powerful men fit into America’s cinematic vision of mob culture. As Renga notes, “Films and series like Goodfellas, The Godfather and The Sopranos depict criminals frequently in highly sympathetic terms, making hardcore villains into likable antiheroes viewers enjoy engaging with.”

Sinatra, himself, eventually became part of that same cultural archetype. “Like much of organized crime history, the public narrative is a mixture of fact and legend,” Jensen says. “Some say the mob made Frank Sinatra’s career… But this story is more legend than fact.”

The alleged link between beloved “Law & Order” actor Jerry Orbach and the mob stemmed from his friendship with New York gangster Joseph “Crazy Joe” Gallo. Their relationship began in 1971 when Orbach played a character based on Gallo in The Gang That Couldn’t Shoot Straight. After learning about the film, Gallo arranged to meet Orbach. Instead of a confrontation, the two became friends and socialized in New York entertainment circles.

The friendship led to speculation. Orbach and his wife were reportedly with Gallo the night he was murdered at Umberto’s Clam House in April 1972. Some reports claim Orbach might have joined Gallo for dinner shortly before the shooting, possibly making him a witness. Orbach never publicly discussed the incident and declined to cooperate with investigators.

Much of the story remains difficult to verify. “To help separate fact from fiction when telling these kinds of stories, we look for documented interactions and credible first-hand accounts, while maintaining a healthy degree of skepticism,” says Jensen.

Lana Turner became entangled with the shadowy world of underground crime through her turbulent relationship with Johnny Stompanato, the bodyguard and close associate of Los Angeles mobster Mickey Cohen. According to Jensen, Stompanato’s romance with Turner was marked by fierce passion and a pattern of intense abuse. In 1957, while Turner was in London filming Another Time, Another Place, an enraged Stompanato stormed the set and pulled a gun on her co-star Sean Connery, after suspecting an affair. Connery supposedly disarmed him, leading to Stompanato’s deportation by Scotland Yard.

Tragedy struck in 1958 after a violent argument erupted inside Turner’s home. During the chaos, Turner’s teenage daughter, Cheryl Crane, stabbed and killed Stompanato, allegedly trying to protect her mother. Although the killing was later ruled self-defense, the highly publicized case became one of Hollywood’s most infamous crossovers of entertainment and organized crime.

One of the clearest documented examples of celebrity ties to the mob involved the friendship between George Raft and Bugsy Siegel, the infamous mobster who helped develop the Las Vegas casino scene in the 1940s.

“Raft knew mobsters growing up, including Siegel,” Jensen says. “The two were photographed together with Raft’s arm around Siegel.”

Raft’s real-life associations added credibility to the gangster roles that made him famous during Hollywood’s Golden Age and helped cement his reputation as one of cinema’s defining mob characters.