Celebrity Gambling Stories

  • Joe Rogan, on his podcast talking about his family history:

    "There was some gambling in my family. My grandmother was involved in running the numbers and she got arrested, and she wouldn't rat them out so they put her in jail for 6 months. She would make sweaters for the guards and shit."

  • Al Michaels talking about the times his father would take him to the racetrack when he was little:

    "In those years, if you were less than 18 years old and you were accompanied by a parent, it didn't matter. But what I would do - he would teach me how to read the racing from past performances - so I had tout sheets when I was like 14 years old...When Roosevelt Raceway had been refurbished in Westbury...on the second day of the meeting at the refurbished Roosevelt Raceway I picked the horse named "Al Jareen" at 75-to-1 and the horse won, so after that I would do tout sheets and the neighbors would come buy them for a buck and a half...and that's how I became "Big Al at Westbury"....I thought [the horse] was a good choice because I looked at the horse and said 'This horse shouldn't be 75-to-1, this should be about 20-to-1'."

  • Jimmy Connors had a serious gambling problem that after retiring from tennis. He said “I was looking for something to replace the tennis, but it shouldn’t have been this. I knew gambling on someone else wasn’t my thing. My best results have come when I’m betting on myself or making my own decisions." His gambling included betting $1 million on himself in the 1992 Battle of the Sexes match against Martina Navratilova. Connors says he bet that he would beat Navratilova in straight sets without losing more than eight games - and had to do it getting only one serve, with Navratilova using half the doubles alley. He lost the bet. Another time, after a bad day on the tennis courts, he bet $60,000 bet and didn't even stick around to see if he won. It was the thrill of the bet.

  • John Daly gambled away between $50-$60 million in career earnings, according to his 2006 autobiography. Daly once lost $1.65 million in five hours playing slot machines at a casino. He also blew $1.2 million in two and a half hours at a casino in Las Vegas. He had his $1.6 million house foreclosed on. In order to deal with his gambling habit, he downgraded from the $5,000 slot machines to the $100-$500 machines.

  • Andrew Dice Clay, talking about his gambling habit: "In the early nineties, I went through some crazy gambling periods. I don't say this to shock you but only to tell the truth: on three straight nights at Caesars in Vegas I lost $700,000 each night at blackjack. That's $2.1 million in less than seventy-two hours."

  • Russell Crowe lost 2,000 British Pounds while on the set of "Gladiator" after he got caught up betting on a competition based on whether or not he could throw oranges into a bucket from a building several stories high.

  • P. Diddy and Mark Wahlberg bet $250,000 on the Mayweather-Pacquiao fight. They put the money in escrow. Diddy bet on Mayweather, and won.

  • Floyd Mayweather appeared on Jimmy Fallon's show and showed his receipt for a $1.1 million bet on Oregon from the previous college football season. He won the bet.


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HPG ADMIN on June 3, 2015