Frank Sinatra Lost Teeth in a Casino Brawl After a Punch by a ‘High-Ranking Mobster’

Frank Sinatra was a prominent figure in Las Vegas history, so much so that casinos would give him free chips when he visited. When management changed, and his perks ended, Sinatra was not happy. According to one of his friends, the star threw a fit when he could not have the casino privileges afforded to him as they were before. The management was forced to react, much to the excitement of the nearby crowd.

Frank Sinatra sits in an orange armchair and holds a cigarette.
Frank Sinatra | Silver Screen Collection/Getty Images

Frank Sinatra and the Rat Pack spent a lot of time in Las Vegas

The Rat Pack was formed in Las Vegas after a particularly debaucherous weekend. Sinatra flew out several friends and by the fourth day, the group showed the impact of late-night parties. According to the book Bogart: In Search of My Father, “they all looked like hell.” Lauren Bacall, who was married to Rat Pack leader Humphrey Bogart, told the group, “You look like a goddamn rat pack.”

The name stuck, as did the group’s influence on Las Vegas. Sinatra, in particular, had an impact on changing Las Vegas into a glamorous place. 

“Frank wouldn’t go out after dark without a sport jacket on, let alone perform out of a tuxedo,” former Nevada Lieutenant Governor Lorraine Hunt-Bono told Smithsonian Magazine. “He was the spark that changed Vegas from a dusty Western town into something glamorous.”

He once got into a fight at a casino over chips

Sinatra often received preferential treatment in Las Vegas. After one point, however, these perks ran out.

“They used to give Frank $50,000 worth of gambling chips and let him keep all the money,” wrote Sinatra’s friend Paul Anka in the book My Way, per the Daily Mail. “But in the late Sixties, when the billionaire Howard Hughes started buying up all the casinos, this perk came to an abrupt halt.”

According to Anka, many of the casinos were mafia-run. They were happy that Hughes took control because it brought focus off them. When Sinatra tried to complain, they waved him away.

“The next night, Frank was still steaming,” Anka wrote. “Suddenly, he stood on the blackjack table in the middle of the Sands casino, ranting: ‘This place was sand when they built it and it’ll be sand when I’m f***ing done with it.’”

Eventually, the casino manager, who Anka claimed was a “mobster,” came to calm Sinatra. He tried to reason with Sinatra, but it did not work.

“Frank was having a full-blown tantrum,” Anka wrote. “He threw a chair at a security guard and scalded Cohen with boiling hot coffee. Cohen punched Frank in the mouth, scattering his tooth caps all over the floor. The entire town applauded Cohen — fuelled by too much drink, Frank’s behavior had been getting more and more abusive.”

Per The New York Times, the fight was brief.

“Frank Sinatra was punched so hard he lost two teeth and got a bruised lip in a one-punch fight,” the paper reported in 1967.

Frank Sinatra reportedly tried to have the casino manager killed

In the aftermath of the fight, Sinatra was still angry. He reportedly told contacts in the mafia that he wanted the casino manager killed.

“But not even the king of Vegas could go around threatening a high-ranking mobster,” Anka wrote. “Frank was warned never to go near him again.”

Even after all this, Sinatra has a restaurant in a Las Vegas casino to this day.

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