Back in 2007, Affleck was reported to have an online poker addiction. Once his marriage transitioned from the honeymoon stage, Affleck turned to playing online poker four nights per week and oftentimes lost more than the GDP of Rwanda in a single night.
The former foreign exchange trader became famous, and incarcerated, after losing $100 million of Barings Bank – Singapore's money. Leeson wasn't interested in being discrete either as he lost the entire sum in one day.
So what if his ex-wife Denise Richards claims that he's lost a ton in casinos? Emilo's brother and Martin's favorite son has f*cked over 5,000 chicks, earning himself the much-deserved handle, "The Machine."
We all know his story: Banned from baseball and shunned from the Hall of Fame for betting on the game he once dominated. His numbers warrant his enshrinement and he never bet against his own team, but the only chance Rose stands to see the Hall in his lifetime is if he outlives or murders Bud Selig.
Donaghy spent 11 months behind bars (and then a few more at a halfway house) after he was convicted of betting on and fixing NBA games that he refereed. His partners in crime were legit gangsters, so in his defense, if he didn't throw those games to manipulate the spread, his friends would have likely introduced him to Jimmy Hoffa.
As of last July, Walker owed a combined $822,500 to three casinos in Vegas. He should be able to wipe that debt clear in no time because outside of being a washed-up and unemployed power forward, Walker is highly qualified to operate a deep fryer.
I didn't rank these, but when a man openly claims to have lost somewhere between $50 and 60 million gambling at casinos over the course of 12 years, you have to reserve the number one slot for him. Daly is a lot of things, but vice deficient he is not.