6 Celebrity Gamblers Who Placed Insane High-Stakes Bets

When the world of celebrities and gambling collide, there is always intrigue! From massive wagers to big wins at major sporting events, these stories always hook fans from all walks of life.

These celebrity gamblers often place their high-stakes bets either at casino tables or via increasingly popular online betting sites, where odds and markets present opportunities to win big. Such wagers consistently cause a stir in the public eye.

In the article below, we will take you on a journey of some of these triumphant celebrities who make bold bets, and we will provide you with insight into why they make such extravagant wagers.

Some celebrities shine on stage or in sports, but a few stand out for their daring gambling exploits. These six individuals have made headlines with bold bets and high-stakes wagers.

Drake's High-Stakes Sports Bets

Drake is one of the biggest rappers in the world. The Canadian often places huge sums of money on lots of events and posts it on his social media.

One of his most famous bets was a $250,000 wager on Jannik Sinner to win the 2024 Australian Open final against Daniil Medvedev. It hit and Drake won $95,000 when Sinner lifted the trophy.

Drake’s betting record is mixed though. In the past, he has lost some big wagers, including a substantial $2 million on a UFC fight between Israel Adesanya and Alex Pereira in 2022.

Despite that though, his profitability and brave betting style makes him standout in the world of celebrities who bet.

Georgia Toffolo’s Charitable Windfall at Cheltenham

The former “Made in Chelsea” star made a huge bet at the Cheltenham Festival back in 2022. Toffolo placed a £5,000 multiple bet on two horses. The bet slip was £2,500 on Constitution Hill to win the Sky Bet Supreme Novices' Hurdle and £2,500 on Jonbon to finish second at eye-watering odds of 14/1.

The reality star pledged to donate her winnings to charity and said that she would support both the British Red Cross and the Disaster Emergency Committee for Ukraine.

It was a great gesture by Toffolo who claimed the win was beginners’ luck and was very humble in victory.

Floyd Mayweather's Attempted Bet on Himself

One of the greatest boxers to ever live, Floyd Mayweather tried to bet on himself! The man with an undefeated record of 50-0 tried to place a wager during his fight with Conor McGregor in 2017. He tried to place a bet of $400,000 at a Las Vegas casino on a 200 moneyline and the fight ending under 9.5 rounds.

Legal restrictions did stop him from placing the bet, as athletes are not allowed to bet on their own events.

Mayweather did collect over $100 million from the fight though, testament to his ability to turn high profits from major events.

Ashley Revell's All-or-Nothing Roulette Spin

Ashley Revell is an entrepreneur from England who made headlines in 2024 for an insane bet. He sold all his belongings which were valued to be around $135,300 and bet it all on a single roulette spin at the Plaza Hotel & Casino in Las Vegas.

Revell placed it on red and won when the ball landed on 7 red! He doubled his money to a whopping $270,600.

Following the miraculous stunt, Revell became famous and soon ventured into online poker.

Brian Zembic's Unconventional Wager

Brian Zembic is a magician and gambler who redefined betting with one of the craziest wagers known to mankind.

He made a bet with a fellow gambler to get breast implants and keep them for a year to win a massive $100,000!

Zembic was not well known in the gambling community but after a stunt like this, he became a household name. His unique bet stands out as one of the craziest of all time.

Jim McIngvale's Record-Breaking Sports Bets

Known in the gambling industry as “Mattress Mack,” Jim is one of the biggest sports bettors in the world. He famously lost $9.5 million wagering on the Cincinnati Bengals to win Super Bowl LVI in 2022.

He made amends not long after when he banked $75 million after his bet on the Houston Astros to win the 2022 World Series came through! It is known as the largest recorded pay-out in sports betting history.

His betting career did see him face some losses. His bet against the Georgia Bulldogs in College football is a significant one but his status as a gambling legend will live on.