The entertainment industry’s portrayal of mobsters has often captivated audiences, but
there has often been crossover between Hollywood and organized crime. When this happens, truth
is just as intriguing as fiction. Let’s take a closer look at Hollywood stars with
real-world connections to the mob.
Frank Sinatra's life as a Vegas crooner put him in the perfect spot to associate with
mobsters, and he did just that throughout his years in showbiz. According to NPR, there
were even rumors he was a, quote, “bagman” for the mafia himself, but those rumors weren’t
necessarily ever verified. However, his connection with infamous underground figures was pretty
darn obvious to anyone in the know.
One of those figures was gangster John "Handsome Johnny" Rosselli a man who bridged the worlds
of organized crime and the entertainment industry. According to Vice,
"[Rosselli was] the virtual godfather of Las Vegas in the '50s and '60s [who] knew most
of the big showbiz stars.”
Having risen through the underworld ranks with the notorious Al Capone, Rosselli was
tasked with, quote, “infiltrating” the Hollywood community. In that role, he served
as an ambassador of sorts, networking not only with fellow mafiosos but also with producers,
actors, and actresses.
“You look terrible. I want you to eat. I want you to rest awhile, and a month from
now, this Hollywood big shot’s gonna give you what you want.”
Sinatra was on his list of known Tinseltown associates, partying with Rosselli and other
mob figures including Chicago mob boss Sam Giancana. The Grammy- and Oscar- winning singer
was so tight with known mafia members that the FBI even had a file on Sinatra and his
mob contacts.
Despite all of this, Sinatra repeatedly rejected law enforcement’s claims that he had mob
connections. While investigators weren’t convinced when the singer disclaimed any ties
with gangsters Lucky Luciano, Meyer Lansky, or Bugsy Siegel, they ultimately couldn't
(or wouldn't) charge him with anything.
Stars with organized-crime associations generally deny them, but singer Wayne Newton admitted
knowing Guido Penosi, reportedly part of New York’s Gambino crime family. What Newton
did deny was knowing about Penosi’s mob ties, telling the Las Vegas Sun in 2000,
"It was ridiculous. [...] What do I know about the mafia?"
When reports came out in 1980 that accused Newton of using his co-ownership of the Aladdin
Hotel to act as a, quote, "front man" for the mafia, there were also rumors that
"[He] was spilling the beans about the Mafia to law enforcement officials."
While Newton insisted that he was ignorant of any wrongdoings, there was danger in the
fact that, as he explained,
"The mobsters didn't know that I didn't know anything about them."
Things got even worse for Newton when, according to the AP, he received a, quote, "mafia death
threat" after being named as a government witness for the trial of alleged mobsters
Guido Penosi and Frank Piccolo. He was even given a bulletproof vest by authorities to
protect him from a hit.
"You're really a magical group of people."
Luckily for Newton, he survived the ordeal, though he probably had to reconsider any connection
he may have had to organized crime.
Johnny Rosselli may have been friends with Frank Sinatra, but he might have been more
than that with Marilyn Monroe. In an interview with Vice, Lee Server, author of the book
Handsome Johnny, stated that
“[Marilyn and Johnny were] close for a while, lovers according to some."
While pointing out that he couldn't confirm this, Server went on to mention another rumor
that Rosselli may even have helped Monroe land her first big role as an actress, in
Columbia’s Ladies of the Chorus.
Though Monroe's connection to a member of organized crime may have helped launch her
career during her early days, it turns out that she might have been mixed up with another
mobster during her final days as well. According to recordings made by George Masters, Monroe's
hair and make-up stylist,
"[She] spent her last night alive at Frank Sinatra's lodge with [Sam Giancana]."
It was the Cal-Neva Lodge in Lake Tahoe, Nevada, and while she was there,
“[Giancana] apparently tried to persuade her not to go public about her affair with
President John F. Kennedy."
Though it’s still a mystery what happened at the lodge, Monroe flew back to Los Angeles
the next day and was found dead that night.
Joe DiMaggio was a famous baseball player, but he also became part of the Hollywood scene
thanks to his marriage to Marilyn Monroe. And while he was known as a Yankees slugger,
according to one conspiracy theory quoted in the International Business Times, Joltin’
Joe hired out a hit on JFK over what he thought was the president and his brother Bobby's
involvement in Marilyn's death. According to proponents of this theory,
"Joltin' Joe was so obsessed with the idea that the Kennedys had his ex-wife Marilyn
Monroe killed that he had a hitman or men kill the president out of revenge."
While that claim likely can't be proven, it turns out that DiMaggio also had a strong
tie to one of the most famous mafia families around.
The DiMaggios were partly related to the Gambinos, who eventually became the kingpins of New
York City’s criminal underworld. As revealed by the Times Herald-Record in 2002, the families
had been brought together by intermarriage dating back more than a hundred years, in
Italy and the US. Also in 2002, the DiMaggio-Gambino relatives held a reunion, during which
“Some of the DiMaggio cousins were looking for possible Mafia types [or even the FBI]
lurking about.”
James Caan has played a mafia figure plenty of times on-screen, such as Sonny Corleone
in The Godfather, Spaldoni in 1990's Dick Tracy, and Frank Vitale in 1999's Mickey Blue
Eyes. As it turns out, his authenticity on screen may be due to the fact that he knows
real-life mobsters.
Caan is a personal friend of Andrew “Andy Mush” Russo, the alleged acting street boss
of the Colombo family who was arrested in 2011 and released in 2013, telling the New
York Post:
"My friendship with Andrew Russo dates back over 35 years, and I've only known him to
be as good a friend as anyone could be to me and my family. […] [He has] always looked
after me like a brother."
Russo is the godfather of Caan’s son Scott, and James even offered to post bail for his
friend while he was in prison. Although Russo did end up serving time behind bars, a judge
ordered him released from jail two months early in 2013 when he was 78 years old, telling
Russo's granddaughter,
"Your poppy will be home soon."
It was surely a development that pleased Russo's family as well as Caan's.
Debbie Reynolds may not be a name that you expect to see on a list of stars who have
been connected to mafia figures, but it turns out that the actress got caught up with the
mob on more than one occasion, for better or worse.
We have to head back to 1960 to pinpoint the iconic actress's connection to the mob. That
was when mafia attorney Sidney Korshak bought a house in Bel Air using a deed granted to
him by Karl's Shoe Stores, Limited. If you're wondering what that has to do with Debbie
Reynolds, well, she was married to the Karl of Karl's Shoe Stores - Harry Karl. According
to Vanity Fair, Korshak also helped make Reynolds rich by arranging her million-dollar Las Vegas
debut. The FBI even noted,
“[Korshak was] present at the opening performance of the Debbie Reynolds show at the Riviera
Hotel in Las Vegas, Nevada, in January 1963."
However, Reynolds's interactions with mafia-types weren't always so profitable. During the mid-'60s,
her company Harmony Productions got involved with the maker of something called a Scopitone
audiovisual jukebox. But soon, right when name artists like Johnny Mathis and Roger
Miller were signing on to make appearances, several key Scopitone investors were later
charged with having ties to the mafia, which stalled sales and likely lost Reynolds a pretty
penny.
Like Frank Sinatra and Wayne Newton, Tony Bennett is another Vegas singer with alleged
mob ties. His connection to the world of organized crime, however, is a little different. While
the other stars knew various mafia men, Bennett got caught up with a woman who was connected
to the criminal underworld. Quoted in the Daily News, author David Evanier claimed,
"[Bennett] had a close encounter of the painful kind with the Las Vegas Yellow Pages after
he caused a jealous wiseguy to see red."
So what exactly does that mean? Turns out that while Bennett was separated from his
second wife, Sandra Grant, during the late '70s and early '80s, he began a relationship
with the girlfriend of real-life goodfella Anthony Spilotro. That was the same mobster
who inspired the character of Nicky Santoro in Martin Scorsese's 1995 movie Casino.
"You said I'm bringin' heat on you?"
Unsurprisingly, that relationship didn't work out: Spilotro whacked Bennett with a phone
book to the head when he found out what was going on. While that was undoubtedly unpleasant,
let's be honest: the outcome could have been a lot worse! Spilotro himself was murdered
in 1986 – as legend has it, buried alive. Yikes!
Liza Minnelli played an adventurous woman who wanted to get the most from her life when
she appeared as Sally Bowles in the 1972 classic Cabaret. In real life though, she was apparently
just as much the pleasure seeker, even if that meant getting involved with a mobster
who was hyper-connected to other entertainers.
According to an article in the New York Post, at one time the actress was romantically involved
with Gianni Russo, who was connected to mob boss Frank Costello. Russo also knew plenty
of stars, including Elvis Presley, whose antics led to a situation in which
"Russo took cover as the King mimicked the on-screen pistol play with real guns."
Gianni's Hollywood networking went far beyond Elvis, though: he was also close with actress
Zsa Zsa Gabor, with whom he had a, quote, “weird date,” and, bringing things full
circle, with Frank Sinatra, who supposedly once tried to slap him. As described in the
New York Post article,
“Russo enjoyed a life that is part Scorsese feature, part manifest destiny, and part skin
flick."
George Raft's name may not be the most recognizable these days, but back during the golden age
of Hollywood, he was a well-known actor. He appeared in classic movies like 1932's Scarface,
1959's Some Like It Hot with Marilyn Monroe, and 1960's Ocean's 11 alongside Rat Pack members
Frank Sinatra, Dean Martin, and Sammy Davis Jr.
As a child, Raft, grew up in the Hell's Kitchen neighborhood of New York City where he was
a childhood buddy of gangster Bugsy Siegel, who, according to Biography, helped build
modern Las Vegas on the back of his criminal empire. As a kid, Raft was also pals with
Owney Madden, who would grow up to be one of New York’s most-powerful Irish-American
gangsters.
As someone who was raised in a rough part of town before going into show business, Raft
followed in the footsteps of earlier stars like Ruby Keeler and Ray Bolger – both of
whom were also from Hell’s Kitchen. Yet, if Raft hadn't found his way onto the silver
screen, he might very well have followed his adolescent friends into the underworld – and
he apparently came pretty close to doing that. So while it may seem like choosing to be an
actor was safer than becoming a mobster, it's pretty clear that the two worlds were intricately
intertwined, and have been for quite some time.
“I’m gonna make him an offer he can’t refuse.”
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