The Most Famous Celebrity Sports Bettors

The world of sports betting is becoming more mainstream with every passing day. The United States is in the process of making sports betting legal across the country. Sports betting sites like My Top Sportsbooks are growing in popularity.

Major pro sports leagues, who once treated gambling sites as if they were the enemy, now embrace the leading betting sites, signing partnership deals to display their logos and in some cases, permit wagering right inside their facility.

With sports betting no longer being shrouded in secrecy, perhaps more celebrities will become open about their betting habits. Certainly, the glitterati, the beautiful people, have been prominent players in the game of wagering on sports for many decades.

Let’s take a look at some of the most famous celebrity sports bettors around today and some of their accomplishments.

James Holzhauer

Holzhauer would probably still be betting and winning on sports in relative anonymity had he not chosen to go on the quiz show Jeopardy and absolutely shatter the television program’s record earnings numbers.

The professional sports gambler from Las Vegas appeared on the show in 2020 and won $2.462 million in only 32 episodes. He fell just shy of the all-time record earnings of $2.52 million garnered by Ken Jennings but it took Jennings 74 episodes to amass his total.

Holzhauer set the single-game winnings record with $131,127, earning him the nickname Jeopardy James. What made his success on Jeopardy so intriguing was Holzhauer employed the same strategies he utilizes as a professional sports bettor while competing on the show.

He bet aggressively, usually selecting the highest-paying clues first in order to maximize his earnings potential. Holzhuaer hit on 97.4 percent (72 out of 76) of his Daily Double wagers. His average Daily Double wager was $9,000. He’d do likewise with his Final Jeopardy wagers.

Holzhauer is the only player in Jeopardy history to win $100,000 in a single episode and he did it six times. His performance on the show gave credence to the fact that there definitely is skill and strategy involved when betting on sports.

Holzhauer moved from Illinois to Las Vegas in 2008 to bet professionally on sports. He says he’s built predictive models for baseball, NFL, and college basketball, but now focuses his betting strategies mainly on in-play wagering.

Michael Jordan

There’s always been a suspicion that Jordan’s shock retirement from basketball in the mid-1990s in order to dabble into pro baseball was a subtle way for the NBA to suspend him for gambling on games.

Whether it’s fact or urban legend might never be determined but it’s no secret that Jordan is a hard-core gambler. The Chicago Bulls legend was often seen at Atlantic City casinos when the Bulls would be playing the Nets or the Knicks. He was always up for a card game, no matter how high or low the stakes might be.

Even during the documentary about those great Bulls teams The Last Dance devoted a portion of one episode to dealing with MJ’s gambling habit.

Charlie Sheen

Whether it was drugs, alcohol or sex, it was readily apparent for years that the actor and star of the TV Show Two And A Half Men is burdened by an addictive personality. Gambling is another of Sheens many vices.

Knowledge of Sheen’s betting ways was presented for public consumption during his 2006 divorce from actress Denise Richards. She listed Sheen’s $200,000 a week gambling habit as one of the reasons for wanting out of the marriage in her petition for divorce.

Sheen, who once successfully wagered $1 million on Manny Pacquiao to beat Oscar De La Hoya in a boxing match, claims he no longer gambles.

Pete Rose

It’s open to debate which was the bigger baseball betting scandal. Was it eight members of the 1919 Chicago White Sox being banned from baseball for throwing the World Series to the Cincinnati Reds? Or was it decades later, when Reds manager and MLB all-time hits leader Rose was also issued a lifetime ban from baseball for betting on games?

It was in 1989 when MLB Commissioner Peter Ueberroth announced that Rose was being investigated on serious gambling charges. MLB lawyer John Dowd reported that he’d found evidence of Rose betting on Reds games while he was player-manager of the ballclub, and also when he was solely managing the team.

Though Rose originally denied all of the allegations, he quietly accepted his lifetime ban. Finally in 2010, two decades later, Rose admitted that he’d bet on Reds games while managing the team.

There’s a regular outcry for Rose to be reinstated to baseball but he’s done little to distance himself from the world of gambling. He’s frequently seen at events like the Kentucky Derby and the World Series of Poker and is always willing to offer his handicapping advice to anyone with a camera or a microphone.

Ashton Kutcher

He’s made a career out of playing dumb guys on TV and in the movies but when it comes to sports betting, Kutcher may be the shrewdest celebrity of them all. He takes a scientific approach to his sports betting, utilizing math and probability laws, seeking out numerical anomalies that influence his wagering decisions.

He once told Esquire Magazine that he was part of a sports betting syndicate that won $750,000 wagering on NCAA football games in the span of four weeks. More recently, Kutcher has invested his money in sports betting companies. He’s a partner in Unikrn, a bookmaker that offers wagering on eSports.

Floyd Mayweather

Money Mayweather, as he’s known, doesn’t mind putting some of his money down on a variety of wagering opportunities. And he also isn’t shy about sharing tales of his gambling exploits.

Mayweather is 50-0 as a professional, and widely regarded among boxing’s all-time greatest pound-for-pound fighters. It’s not known what his gambling record is but he does brag about some big scores.

He’s posted photos of many winning bet slips on his social media accounts. From 2010-12, Mayweather claims he cashed 46 successive winners that he’d played at various sports betting sites.

(guest article)

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