2 Fast 2 Furious (2003)
The Fast and The Furious: Tokyo Drift (2006): Fast and the Furious, The: Tokyo Drift (2006)
Cops O: Late Night Snacks
Cops O: The Young and the Reckless
Cops O: Front Door Felony
Cops O: From Sixty to Zero
Cops O: Bible Buddies
Cops O: Manic Monday
Cops O: The Young and the Reckless
Cops O: Front Door Felony
2 Fast 2 Furious (2003)
The Fast and The Furious: Tokyo Drift (2006): Fast and the Furious, The: Tokyo Drift (2006)
Xtreme Off Road: XOR Adventure Ride
Engine Power: Ford Tribute: Big Inch Windsor Stroker
Detroit Muscle: Barn Find Chevelle: Shiny Bits and Panel Fits

Seven Celebrities with Surprising Gambling Problems

by davidbreitman   November 22, 2010 at 10:00AM  |  Views: 29,259

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