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Frank Sinatra lost teeth in a Las Vegas casino fistfight over massive money fall out

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Frank Sinatra was renowned for being a big shot in America throughout the 1950s and 1960s – and with good reason. The iconic singer would attract thousands of fans to wherever he was playing and sold more than 150 million albums across his career.

So then, Old Blue Eyes expected to be treated with a certain degree of respect. And most of the time, he was. In particular, at casinos, he would be treated even more special than usual.

Because of the money Sinatra had earned for the various casinos in Las Vegas, Nevada, he was often given preferential treatment as soon as he walked through the door. On top of being given the best gambling spots in the house, he would also be fuelled with the finest free drinks and food.

His mere presence in the building would attract even more punters to the casino, so he would be doing the various establishments favours by just turning up to do some gambling.

But the biggest attraction for Sinatra was that he would be given thousands of dollars worth of free casino chips.

Sinatra’s friend Paul Anka revealed the star was given up to five figures in chips just for arriving.

“They used to give Frank $50,000 worth of gambling chips and let him keep all the money,” Anka wrote in his book My Way.

However, things weren’t destined to stay that way. As the years rolled on, the people in charge of the casinos changed, and Sinatra was no longer well respected. Anka wrote: “In the late sixties when the billionaire Howard Hughes started buying up all the casinos, this perk came to an abrupt halt.”

Sinatra was not happy.

He complained to the most senior person he could find, but he was “waved away”. Sinatra left the casino, furious with how he had been treated. But the next night, he returned. And he was not going to be taken for a fool again.

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Anka said: “The next night, Frank was still steaming. Suddenly, he stood on the blackjack table in the middle of the Sands casino.”

Sinatra screamed at the top of his lungs to the casino-goers: “This place was sand when they built it and it’ll be sand when I’m f***ing done with it!”

When the casino’s manager came to quell Sinatra’s problems, the singer accused him of being a “mobster”. Any reasoning with Sinatra simply wasn’t working. And, after a short while, tempers flared and things got out of hand. Sinatra started throwing things around.

Anka wrote: “Frank was having a full-blown tantrum. He threw a chair at a security guard and scalded Cohen with boiling hot coffee.”

He added: “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 behaviour had been getting more and more abusive.”

The New York Times corroborated this event, as it was reported the following day in the news section.

The publication wrote in 1967: “Frank Sinatra was punched so hard he lost two teeth and got a bruised lip in a one-punch fight.”

On top of having a bruised lip, Sinatra’s ego was particularly bruised.

Anka wrote that the singer wanted “to get his mafia contacts to kill the casino manager”. Anka added: “But not even the king of Vegas could go around threatening a high-ranking mobster. Frank was warned never to go near him again.”

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