Fighters & Gambling

Big fights in Vegas generally mean one thing—a massive payday for the local bookmakers.

There’s just something about the sport that has fans all over the world rushing to their nearest sportsbook to drop a few dollars on who they reckon is going to be the winner.

Of course, fighters rarely get involved in the sports betting action especially when it’s their own fight; unless your name is Mayweather that is.

With Vegas being the spiritual home of boxing, it really should come as no surprise that some of the world’s most famous fighters are big gamblers.

Here are a few of the biggest:

Mike Tyson

Possibly one of the greatest fighters of all time, but iron-Mike is almost as famous for losing all his money as he is for winning the championship of the world.

In his heyday, when money was no issue, Tyson loved to bet on sports. He was known to hit the casino sportsbooks and drop huge amounts of money on what he felt were sure things.

He was even said to be obsessed with state lotteries and would spend big in the hopes of snagging a jackpot. You can see where this is going though, right? Tyson was never what you would call a successful gambler. In fact, much of his financial losses can be directly attributed to his crazy betting habits. Legendary boxer, but a truly terrible gambler.

Floyd Mayweather Jr.

Floyd ‘Money’ Mayweather Jr. is possibly one of the biggest gamblers in boxing. He’s known to spend a great deal of his time in casinos at the sportsbook picking long shots to bet on. He has even been known to try to place bets on himself to win his fights.

For his big fight against Conor McGregor in 2017, Floyd tried to wager $400k on himself to win the fight in under 9.5 rounds while he wanted to place another on a win by knockout.

He wasn’t in luck though as none of the local bookies would take his bets. His biggest win at the bookies was when he took home over $827K for a $350k parlay bet on a boxing match and a basketball match.

Interestingly, while Money enjoys betting on sports, he also loves the blackjack table. Those who have seen him play say that he regularly bets $100k on a hand and will even hit on a 17. Anyone that understands the basics of blackjack knows that it’s best to stand on anything that’s 17 or over. But asking for another card when there’s $100k on the line just goes to show how much Floyd enjoys the thrill of the bet.

Tyson Fury

The two-time world heavyweight world champion used to enjoy a flutter at the casino. In fact, he loved playing at the table so much that after beating Otto Wallin in Las Vegas, Fury decided to see how far his winning streak would take him.

After the fight, Fury was taken to University Medical Center in Vegas for treatment on two bad cuts. He received an incredible 47 stitches before signing himself out and heading straight for the strip. He went back to the casino, had a few beers and played a few games. He eventually left with $5,000 in his pocket. Chump change considering his fight purse but impressive given the condition he was in post-fight.

However, since then Fury has made the decision to go teetotal and has even said that he will no longer endorse any gambling companies due to the struggles of a close friend.

Vinny Pazienza

Now known as Vinny Paz, Pazienza is a former lightweight and light middleweight world champion who hails from Rhode Island. He was a great boxer but like Mike Tyson, not so great a gambler.

Paz loved the casinos and would regularly wager six-figure amounts at the poker table. Things went sour when it was discovered that he issued bad checks to a Las Vegas casino following his losses. He also invested quite a lot on the stock market, but lost it all and racked up huge debts.

Evander Holyfield

This is another sorry tale of a boxer who lost it all at the casino. Evander Holyfield built up a net worth of $150 million at one point in his career. But his penchant for backing the wrong horse (quite literally) saw him lose it all in the most spectacular of fashions.

Paternity suits and divorces all took their toll and Holyfield spent what was left of his money throwing good after bad at Atlantic City casinos.

Manny Pacquiao

One of the most-loved fighters of all-time and the one fighter who genuinely gave Mayweather a run for his money, Pacquiao is a well-known gambler. He visits the casinos of Macau on a regular basis and wagers massive amounts on sports.

Like Mayweather, Manny was known to place bets of $100k or more regularly and was said to have once placed a bet of over $360k on a Philippines cockfight. Great guy and an even better fighter but come on, betting on cockfighting? We thought you were better than that Manny.