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Real Estate Gamble

[Blind Gossip] If you are wondering why this celebrity is selling off property, we may have some insight!

He has a gambling problem. A bad one. He literally has gambled away millions of dollars in a single month. The bookies love him and hate him because he bets big, but he doesn’t always have the cash to pay off his bets. He needs to get more liquid.

Not Ben Affleck, who has been banned from the blackjack tables at a Las Vegas casino.

Similar: All The Old Habits

Celebrity:

[Optional] Do you gamble? What do you gamble on?

Reader Interactions

Comments

  1. At first I was going to say Michael Jordan but I wonder if this could be that other former Chicago Bull who was polar opposite of Jordan because he was renown for his Defensive skill Set , Dennis Rodman. Rodman loved the Casinos and he was known for going through money as if it was being fed into his bank accounts from another dimension. Could be Toby Maguire but he strikes me as being a more careful almost Professional Gambler even if he is a * !

  2. A-Rod would be unlikely, as someone working on building a business based on his personal brand – I don’t see J-Lo being associated with that after Affleck, either. But Jeter I can see, and millions in a month would fit him better than Phelps. He’s got endorsements but swimming doesn’t pay like baseball! Depp is basically bankrupt and his spending habits are well documented. Gambling’s never come up, and ruling out those w/ a known history of gambling (e.g., Jordan) b/c it wouldn’t be a…

  4. I’ll go along with another poster and say Michael Phelps. The clue? ‘…..he need to get more LIQUID!’

    • YES. About 4 years ago he got a DUI after leaving an 8 hr gambling binge at the Horseshoe Casino. He is addicted to blackjack and poker. The need to win I guess.

  6. Just give me one of his millions. I will buy a truck and a camper and live on the rest.

  8. Celebrity: A-Rod.

    Hints: Ben is a famous JLO ex and he is a famous JLO current.

  14. Derek Jeter

    No gambling here….well, I did take a gamble on love once and won big time. I quit playing after that and have been married 30 years this summer. <3

  15. James Woods
    Occasionally gamble on powerball/lottery but rarely. The odds of winning anything on those are awful.
    Used to like to play poker but the people I played with are dead or moved away.

  16. Elton John is selling his mother’s house
    And he has a regular gig at Ceasers Las Vegas
    I only gamble on bingo now and then.

  20. Celebrity: I’m going with Michael Jordan

    [Optional] Do you gamble? What do you gamble on? $5 a week on lottery.

  23. He needs to get more liquid…

    Michael Phelps.

    He’s selling his Scottsdale home for way above market value. Has also had a gambling problem in the past.

  24. Tobey MacGuire?
    Don’t know if he’s actually selling property or not, but he’s definitely got a major gambling habit on top of being an absolute douche nozzle.

  26. Derek Jeter?

    He is selling some stuff but I would be surprised – thought he was smarter than that.

  27. Michael Phelps just put some real estate on the market, but not sure this is about him.

    I don’t gamble at the casinos very often (maybe once or twice every 5 years), but when I do go to LV or AC, I have a budget of exactly $100 to use for gambling. I figure it’s the same amount I’d pay for a night out.

    I do play in the office pools for the SuperBowl and the Sweet 16 tournaments. We all chip in $10 or so. It’s fun.

  28. Derek Jeter.
    I do not gamble. I would rather donate extra money to charity or to the homeless.