Question of the Day - 11 March 2025

Yes, Frank Sinatra dealt blackjack at least once that we know of at the Sands in Las Vegas during the Rat Pack era. It was a combination publicity stunt, interaction with high rollers and show-goers, and a way for the bossy Sinatra to assert himself in the casino in which he owned a couple of points. 

Dean Martin also dealt blackjack at the Sands when the mood struck him. in his massive biography of Martin, writer Nick Tosches documents instances of this in March 1956 and January-February 1959. Given Dino’s legendarily low threshold for boredom, doubtless there were other larks in the table-game pit.

It was all part of the larger-than-life Vegas experience Sinatra, Martin, and the other Rat Packers helped define in the 1950s and '60s. Also, if anyone in management was bothered by the shenanigans, they could console themselves with the thought that Martin was good for business. As Variety chronicled in November 1965, “He’s a pet of the pit bosses, because when he’s around, the money’s around.”

To that extent, Sinatra and Martin were also inveterate gamblers and they played a lot of blackjack and baccarat whenever they performed or were in town on other business. Martin and Sammy Davis Jr. were good tippers and, more importantly, good losers, whereas Sinatra was neither. Dealers hated dealing to the mercurial and entitled star, who was known to tear up a card he didn't like and demand a new one. In 1983, New Jersey gaming officials investigated allegations that Sinatra intimidated a blackjack dealer into altering the rules when he played at the Golden Nugget, his friend Steve Wynn's joint at the time. A year later, Golden Nugget was fined $250,000 for infractions by the dealers, who were suspended, during that blackjack game. A New Jersey Casino Control Commissioner at the time called Sinatra "an obnoxious bully," prompting him to cancel all appearances for a while in his home state.

Interestingly, Sinatra was always polite to the other players at the table. And boy, were there other players. Frank liked to sit down at an empty table at the Sands and watch how fast it filled up. Indeed, the whole casino was suddenly teeming with gamblers; word traveled fast up and down the Strip that Frank was firing it up at the Sands and people came running. 

Needless to say, the Sinatras, Martins, and Davis, Jr.s of today could never get away with invading a casino pit, let alone dealing to players. Casino dealers must be licensed by the Nevada Gaming Control Board, which involves background checks, training, and certification. Even as a publicity stunt, no entertainer could pull of what the Rat Pack did. 

Casinos find other ways to involve celebrities. They might have a star host a charity tournament, make a special appearance at a high-limit table, or even sit in as a "celebrity guest" at a game without actually dealing. 

And as for celebrity players, the best-known are Ben Affleck, Paris Hilton, Bruce Willis, Ray Romano, Michael Jordan, 50 Cent, and Machine Gun Kelly. And yes, they do attract crowds.