Question of the Day - 14 April 2025

Yes, Gladys Knight has been open about her struggles with gambling in the past. She admitted in her memoir Between Each Line of Pain and Glory: My Life Story that she had a serious gambling addiction, particularly with baccarat and sports betting. Knight has confessed that she lost "significant amounts of money" before ultimately overcoming her addiction with the help of her faith and support system. However, we couldn't find any references to the specific figures you mentioned in the question or any numbers, for that matter. In addition, she's not widely known as "a celebrity who was a perennial loser"; instead, her story is often framed as one of overcoming addiction, rather than being a cautionary tale of financial ruin.

As for other celebrities with admitted gambling problems, Ben Affleck is certainly the first who comes to mind. A skilled poker and blackjack player, Affleck was allegedly banned from the Hard Rock here for being too good at counting cards. He's acknowledged struggles with gambling addiction, which has reportedly led to significant losses and controversy. His losses are estimated to have hit $10 million, though we hasten to add that number is decidedly unconfirmed.

Charlie Sheen is known for gambling vast amounts of money. He's publicly acknowledged losing "hundreds of thousands of dollars," including a reported $200,000 in a single blackjack session and another $165,000 in one long night at the tables. At his peak, he's been reported as gambling $200,000 a week. 

Comedian and actor Ray Romano has spoken openly about gambling addiction. He admitted that Gambler’s Anonymous helped him deal with his betting habits and that those experiences informed his role as a compulsive gambler in the TNT series "Men of a Certain Age."

In a 2008 interview with ESPN, basketball player and analyst Charles Barkley admitted that he'd lost "probably $10 million" gambling. He called it "a stupid habit that I’ve got to get under control," which as far as we know, he eventually did.

Pam Anderson also has some gambling losses in her past. In 2007, she told Ellen DeGeneres on her show that she paid off a $250,000 poker debt she owed to poker pro Rick Salomon with "sexual favors" (reported at the time as "a kiss"). Apparently, the "favors" worked in both directions; Pam and Rick were married and divorced twice. 

Michael Jordan's appetite for gambling is legendary, with reports of losing millions on golf bets, poker, and casino games. He once wrote a $1.25 million check to cover his losses.

Former NBA star Allen Iverson, former professional boxer Floyd Mayweather Jr., golfers Phil Mikelson and Tiger Woods, rapper/actor Nelly, Paris Hilton -- the list goes on and on -- have all been in the news at some point for the levels at which they play, though not because of any admission or evidence that gambling for them is a "problem," and it's important to understand that losing large sums also doesn't indicate same. In the cases of Jordan, for example, it's safe to assume that whatever amount he may have lost is relatively inconsequential to his financial well being. There's no doubt that some celebrities are among the 1%-2% of the U.S. population estimated to experience problem gambling, but it's also true that their losses tend to be more public and staggering, which skews perception.