Top 7 biggest high roller celebrities

Estimated reading time 3 minutes

For most of us, making a bet at our favourite online bookie, online casino or even the local bricks and mortar casino is a pretty tame event – losing a $100 or so is a big deal to us small potatoes. But for the people in the world who earn millions and are worth billions, a casual flutter can result in massive wins or even gargantuan losses. Here are our top seven celebrity high rollers.

7. Ben Affleck

Ben Affleck is an enigma wrapped in a riddle. The guy has won two academy awards but conversely starred in such dynamic cinematic classics as Reindeer Games, Phantoms and Gigli. Affleck has made quite a name for himself outside of the acting world as a pretty handy poker and blackjack player – in 2004 he won $356,400 at the California State Poker Championship.

Since then, Affleck’s infamy in punting circles has grown since he was banned from playing blackjack at the Hard Rock Hotel Casino for allegedly counting cards.

6. Tobey Maguire

Maguire hasn’t done much of note on the screen outside of the Spiderman trilogy but he slings a lot more than web when he is at the poker table. Maguire is known to be quite the shark.

It has been reported that throughout his poker career, Maguire has pulled in more than $10 million worth of winnings.

It hasn’t all been roses and poker chips for Maguire though. The actor settled a lawsuit in 2011 after being sued for winning more than $311,000 from Bradley Ruderman, who funded his poker games off the back of a Ponzi scheme he was running. Maguire had to repay $80,000.

Maguire is a regular on the World Poker Championship circuit.

5. Dana White

The UFC president is known to be quite a prolific punter. White often boasts of walking away with more than $5million after a session at the blackjack tables and has been known to bet $50,000 a hand.

White’s winning ways have even seen him asked to leave The Palms in Vegas twice and has reportedly been banned from playing at several other casinos.

4. Tiger Woods

Tiger Woods is good buddies with NBA stars – and mad keen punter too – Michael Jordan and Charles Barkley. Woods is a regular among several casinos in Vegas and even has a $1 million betting limit at the MGM Grand.

Woods’ poison of choice is blackjack and he has been known to play as much as $200,000 per hand at the blackjack table.

Estimates have Woods having lost more than $50 million on the punt. Sure some casino operators have verified him walking away with the odd million or two, but outside of that it seems Woods’ blackjack action is usually more one-sided.

3. Kerry Packer

Media mogul Kerry Packer was one of the biggest punters going around before his death in 2005 from kidney failure.

In his day though, Mr. Packer was a prolific baccarat and blackjack punter, known to spend hundreds of thousands of dollars on a single hand. There is the time at the MGM Grand in 1997 that Packer is rumoured to have left with between $20 and $40 million thanks to playing multiple hands at $200,000 each at blackjack.

Or there was the time a belligerent Texan oil man boasted that he was worth $100 million, so Packer turned to him with a coin and said, “If you really want to gamble I’ll flip you for it.” The Texan calmed down after that.

Better than that was his famous generosity when it came to tipping waitresses and dealers. He would often ask if they had a mortgage, how much it was, and then offer them a tip to pay off their mortgage.

2. John Daly

The wild living, renegade golfer is one of the most interesting and biggest spending celebrity punters going around.

He has recently come out and claimed that via his personal tax records he has calculated his losses through casinos at approximately $90 million. Not chump change by any stretch of the imagination.

He recalls winning $750,000 at a WGA tournament and then hopping a car straight to Vegas, where he blew the entire $750K as well as another $900,000 from his own kick on top of that.

1. Floyd Mayweather Jnr

With a nickname like “Money” it isn’t hard to believe that Floyd Mayweather Jr is one of the richest sports stars in the world today. With all that money comes a bit more freedom to be very “liberal” when it comes to the punt.

Mayweather is so proud of his countless gambling wins that he regularly posts his betting slips or screen grabs of wins to his social media accounts.

“Money” once had a run of 46 successful bets which brought him in a total of $3,938,722 between August 2010 and February 2012.

In 2013 he dropped $5.9 million on the Miami Heat to beat the Indiana Pacers, eventually winning himself $6.49 million.