Five celebrity gamblers, Charles Barkley, Ben Affleck, Paris Hilton, Tobey Macguire and Gladys Knight have one thing in common – they’ve had their gambling practices scrutinized in the media. Each celebrity had their own approach to gambling. For example, Hilton isn’t viewed as having a problem – she happened to win big at Blackjack on her birthday. And Barkley, while he admits there may be a problem, he quickly brushes the thought aside because Barkley can afford to gamble. Knight took her gambling to heart and sought help. Affleck continues to play and win huge, according to one report. Macguire was accused of holding high-stakes soirees and paid a settlement to bankruptcy trustees last year.
Barkley is only 50 years old, but has lost at least $10 million in gambling. He’ll say he has a gambling problem, but in the same breath, Barkley says he has a lot to spend and can afford it. He believes he should try to curb his gambling, however, Barkley isn’t going to quit. When he wins, he doesn’t feel like it’s a lot. He only feels the pinch when he loses, and he says he’ll never try to beat the casino because it’s simply not possible. He likes gambling – it’s fun and exciting. Barkley enjoys gambling. It’s his money and his life, he says. As long as Barkley keeps making big money, look for him to keep spending big money.
Affleck notably won $800,000 on Blackjack. He tipped casino employees $150,000 of it and went to sleep off a hangover. Affleck was drunk when he bet $20,000 on three hands of Blackjack and won. He seems to have the golden touch, especially for a famous Hollywood poker game that raises money for charity. Blackjack isn’t Affleck’s game of choice – it is said he is exceptional at poker like celebrities, Coolio and David Schwimmer. In 2004, Affleck won $356,000 playing poker. He may also play online poker, according to reports.
She isn’t a member of any A-list poker team, but Hilton partied on her 31st birthday at a Las Vegas casino and tweeted she won $30,000. Hilton stepped up to a Blackjack table wearing a glimmering cocktail dress and dominated. Her tweet said she loves gambling. Hilton, who hadn’t been in the media much before the win, made the tabloids and national news for her win, which was posted online with the wins of big gamblers, Ben Affleck and 50 Cent.
Macguire is said to be an intelligent, high-stakes player in hold’em games, participating in private celebrity poker in the Hollywood Hills. He may not always choose the right people to play with, however. Macguire was pursued by bankruptcy trustees after a fund manager went to prison for scamming clients. The manager said he played with Macguire at chic hotels in Los Angeles and lost $5.2 million because Macguire is just that good. In one year, Macguire won $300,000. The winnings weren’t his, say the trustees, because he won the money illegally. California law dictates poker games must be licensed and none of the games the fund manager played with Macguire were licensed. Macguire ended up paying $80,000 in a settlement, a fraction of what he had won. He continues to play.
Knight was a homebody in Las Vegas when she wasn’t performing. One day, a friend asked her if she wanted to play Blackjack. Knight loved it until she won $60,000 in one game and lost it all at the same table. She said a person should never win because winning is how people become addicted. Once a person wins, they don’t expect to lose. She thought her gambling was ridiculous after losing the $60,000. Knight walked from the Blackjack table to the telephone and called for help. A woman on the support line for gambling asked Knight where she was because someone would come and get her. Before she received help, Knight reported losing up to $45,000 a night on the baccarat table. She even called casino employees “family,” and said it was nothing for her to get out of bed and visit the casino at 2 a.m. Knight, who was always a private person, said her gambling was too public and she was out of control. She was ruining her name, she said.