Seven Celebrities with Surprising Gambling Problems

November 22, 2010

You know the old saying "it's all fun and games until a large tattooed gentleman repossesses your child's bicycle while your wife stands in the front yard gently sobbing into a pile of Lotto scratch tickets?" Well, here are seven celebrities whose parents didn't read them that bedtime story.

Gene Lower/Getty Images Entertainment/Getty Images

7. Allen Iverson

Generally speaking, 35-year-old men with neck tattoos and extensive criminal histories are a beacon of sound financial decision making. That’s why, when a report surfaced that unregistered weapons collector Allen Iverson had “gambled and drank away all of his money,” the financial world was dumbfounded.

According to Stephen A. Smith of ESPN, “Iverson's gambling problem is serious enough that he has been banished from casinos in Detroit and Atlantic City.” Sure, being barred from Detroit doesn’t exactly seem like a punishment, but the financial tolls his issues have taken on his personal life have had serious repercussions. Just ask the 11 foreign gentlemen who now play next to Iverson on the Turkish basketball team he had to join in order to help rebuild his diamond necklace portfolio.


6. Phil Mickelson

Stanley Chou/Getty Images Sport/Getty Images

On the exterior, Phil Mickelson might look a perfect physical specimen. A sexual icon in the sporting world who possess the dashing good looks of a young Milton Berle and raw sexual power of a Caesar’s Palace Greek statue. Teenage girls want him and men want to be him.

However, deep beneath his perfectly chiseled exterior lays a dark and seedy character flaw that has made him a conflicted hero with inner demons and a questionable mid-range putting game. Yes, Phil Mickelson has a gambling problem.

According to an article I wrote last week (yes, it’s customary to quote yourself):

The caddie cliques around golf [note] that Mickelson switched from Titleist to Callaway last September “because he has run up considerable gambling debt [and Callaway agreed to pay it off].”

Why do bad things always happen to beautiful people?

5. Ben Affleck

Phillip Massey/Getty Images Entertainment/Getty Images

Ben Affleck is a walking, talking and gum chewing (but not at the same time) answer to the age old question “Is it really a problem if you’re winning?” proverb that the gambling Gods have been battling for years.

As a fixture on the celebrity poker circuit – which often features A-listers like David Schwimmer and Coolio - Affleck has made a name for himself by taking money from people who mistakenly thought that the “Hollywood Hold ‘Em Charity Showdown” was all about raising money and begging Kathy Griffin to please stop talking.

Though Affleck is largely celebrated for his ability to match wits with Jerry O’Connell in the poker world, he gained his most gambling related fame on a trip to Las Vegas in which he drunkenly wagered $60,000/hand on blackjack. The Good Will Hunting star ended up walking away from the tables with $800,000 in his pockets (minus a $150,000 tip to casino employees) and a wicked hangover to commemorate the evening.

Hopefully Affleck kept some of his drunken winnings, as reports have begun to surface that he has since become addicted to online poker, wagering (and ultimately losing) up to $20,000/night.

4. Charles Barkley

Donna Ward/Getty Images Entertainment/Getty Images

Rather than try to explain the psyche of Sir Charles, let’s take a look at what he said after it was revealed he has lost at least $10 million gambling over his lifetime. 

"Do I have a gambling problem? Yeah, I do have a gambling problem but I don't consider it a problem because I can afford to gamble. It's just a stupid habit that I've got to get under control, because it's just not a good thing to be broke after all of these years. I gamble too much, I gamble for too much money," he said. "And it's something I have to address. I am addressing it, that would be the best way to explain it. I'm not going to quit gambling because it's my life and it's my money."

Perhaps the most depressing part of this story is that deep down, Barkley has to be jealous of Ben Affleck.


The Top Nine Things You Didn't Know We're Based on Sex

The Top Seven BJ's That Ruined Everything

The Seven Technologies That Would Make the Robot Apocalypse Inevitible

The Top 10 Lamest Candy Brands

The Seven Celebrity Offspring That Didn't Blow It

The Top 10 Teams Nobody Would Miss if They Went Away

3. Charlie Sheen

Mathew Imaging/Getty Images Entertainment/Getty Images

Normally, it’s not a good idea to believe the psychotic divorce ramblings of a woman known as “the hot chick who made out with Neve Campbell in that crappy Matt Damon movie 15 years ago.” However, given his track record of prostitution and mediocre sitcom acting, perhaps it’s not irresponsible to believe Denise Richards claim that Charlie Sheen has lost copious amounts of money betting on everything from sporting events to casino games.

Ironically enough, has actually posted gambling odds on what Sheen will get arrested for next. If it wasn’t a conflict of interest, Sheen might take some serious action on “gun.”

Odds on what Charlie Sheen get arrested for next:
•    Drugs                                    5/1
•    DUI                                       3/1
•    Gun                                       5/1
•    Domestic Violence                   7/5
•    Prostitute                               5/6

2. Michael Jordan

Andrew Burton/Getty Images Sport/Getty Images

There are two things that Michael Jordan is better at than anybody on the planet:
1)    Being an a-hole.
2)    Gambling copious amounts of money on himself.

He’s also apparently pretty good at basketball, but that’s not important.
The asshole thing became pretty apparent during his infamous Hall of Fame induction speech/pat on the back, but where does his gambling lore come from?

Answer: The golf course.

Jordan famously bet $1 million on a single hole of golf and is rumored to play six-figure games several times a week. In terms of dollars wagered, there is no other celebrity and/or underwear salesman who compares to number 23.

1. Gladys Knight

Kevin Winter/Getty Images Entertainment/Getty Images

A walking answer in the nature vs. nurture debate, Knight was not born into gambling addiction, but rather developed it through years of Las Vegas living and occasional Reno slumming.

In an interview with JET, Knight – who would lose up to $45,000/night playing baccarat said that, “The pit bosses and dealers became my family. I felt protected. I lost my way for a while. I had gotten to the point where I would spend things that I shouldn't have been spending. I was in debt to a degree. It hurt me to hurt my family. I know people were talking about it, saying, 'She's got a problem.' I've always been a private person, but it was getting to be a very public thing. In a way, I was ruining a good name. I'd get out of my bed and go to the casino at 2:00 a.m. I was out of control.”

Like all great articles, it's important to end on a depressing cry for help. Happy gambling!


The Top Nine Things You Didn't Know We're Based on Sex

The Top Seven BJ's That Ruined Everything

The Seven Technologies That Would Make the Robot Apocalypse Inevitible

The Top 10 Lamest Candy Brands

The Seven Celebrity Offspring That Didn't Blow It

The Top 10 Teams Nobody Would Miss if They Went Away