May 16, 2025
For those seeking thrills and entertainment, sports forecasting is an exhilarating pastime which transcends boundaries of all kinds, no matter if you’re an everyday Joe staking a few dollars or a millionaire who enjoys forecasting lavish amounts. Nothing compares to the excitement of coming out on top with some big winnings.
Get to know some of Hollywood’s well-known celebrities and the globe’s most successful sportspeople who have been known to place bets on sporting events.
As Drake’s enthusiasm for music is widely known, just as popular are his fondness for sports forecasting activity. The Canadian rap sensation routinely visits Las Vegas in between musical and/or touring pursuits, to spend time at sportsbooks. Drake is also a regular at certain online forecasting sites, as such, in Dec. 2021 the superstar artist collaborated with crypto Stake where he registered as DeepPockets6.
Taking chances has been a major pastime for Drake: the 36-year-old is not afraid to publicly document his wagering escapades, which amounted to a total of one billion dollars in the past 12 months. From what can be seen on social media, it appears that he enjoys a thrill or two when participating in sports gambling.
Causing a furor, hip-hop artist Birdman – reportedly a supporter of the New England Patriots – took to Instagram prior to Super Bowl LII, a year with one of the best superbowl ads, and made an eye-opening $100k wager against rapper AR-Ab that the Patriots would emerge atop the Philadelphia Eagles.
But the stakes quickly escalated to a total of $200k. That was, curiously, until both posts suddenly disappeared from Birdman’s page.
Finally, the Eagles came out victorious with a victory score of 41-33 against the Patriots. After the game, AR-Ab took to Instagram and flaunted a selfie with lots of money.
On the other hand, Birdman’s posts kept mum about the wagered bet. People began speculating whether he had paid out the 200k he seemed to have lost. It is clear that if he had not paid up his debt, AR-Ab would have surely made it known.
The iconic Michael Jordan was the epitome of basketball success, yet he could not experience the same level of excellence on his forecasting ventures. Despite the NBA’s strict rules on gambling, whispers and rumors pointed to Jordan’s “retirement” being an investigatory suspension due to allegations concerning his risky habits.
Michael Jordan, the illustrious former Chicago Bulls star, admitted to suffering immense financial losses, the greatest amounting to $165K at an Atlantic City club.
Not to mention, Richard Equinas profited a further $1.25 million from a high-stakes round of golf with MJ. Additionally, some have speculated that there may be even more unrevealed monetary losses.
Having secured the top spot on Forbes’ ranking of highest-paid athletes during his career as a boxer, Floyd Mayweather is no stranger to capitalizing on lucrative opportunities. His determination to succeed has found its way into his fondness for sports forecasting, a hobby that generated substantial sums during the champion’s prime years.
Mayweather has a track-record of publicly flaunting his wealth and possessions. His passion for sports forecasting is no exception. More so, his flamboyant displays of opulence remain a common theme.
Music mogul Curtis ’50 Cent’ Jackson lurches into the highlights again as he showcases his sports forecasting escapades on social media. Recently, he wetted the public’s appetite with his announcement of a $500,000 payday when he correctly wagered on the Giants winning the game against the 49ers.
Rapper 50 Cent doesn’t back away from the adverse consequences of gambling, unlike Money Mayweather. Showing his vulnerability in his songs, he relates his struggles with forecasting , rapping “I got a gambling problem” and “I lost money when I bet on Roy”. In 2006, he openly spoke about his experiences addressing the necessity of dealing with the problem.
The English premier league star has not only enjoyed a highly successful career in football, having featured for Manchester United and Everton, but also became known for his interest in sports forecasting . This was first revealed to the public when he was interviewed at the start of the year.
During the captivating conversation, the ex-soccer star candidly admitted to having a troublesome addiction to taking risks on sporting events early on in his distinguished career. Although not much was revealed in terms of detail, the world-class athlete had a clear affinity for sports forecasting.
Charlie Sheen has certainly amassed a great deal of capital in sports forecasting. Reports suggest the actor, whose wild behavior includes substance misuse and forecasting, is fond of gambling.
During his time on the popular sitcom Two and a Half Men, Charlie Sheen was notoriously reported to earn an awe-inspiring $1.8 million per episode. His former spouse Denise Richards suggests that Sheen’s passion for gambling was much higher than expected, with her claiming he spent up to a colossal $200,000 in wagers every week.
In 2013, Ashton Kutcher’s post-Two and a Half Men career reached an interesting place. He was recruited to be part of the largest sports forecasting syndicate in the country, placing wagers on college football games. Leveraging his public image as “a cash-loaded comedic actor,” the collective used him to mask their activities.
In an interview with Esquire, Ashton Kutcher revealed that he and his team had earned a massive sum of $750,000 in mere four weeks through forecasting on college football games. Their returns on the wagers were quite profitable.
All in all, the amount of famous figures taking part in sports forecasting is unsurprising. Apart from the mentioned above, there are actually plenty of other famous personalities and professional athletes wagering on sports activities due to their adoration for it. It’s evidently been making waves in the world of pop culture, quickly becoming a well-renowned pastime.
Forecasting enthusiasts and casual gamblers alike have a lot in common when it comes to their enthusiasm for wagering on sports. All things considered, it’s easy to see why wagering is so popular.
Many celebrities and athletes are drawn to sports betting for the thrill and entertainment it provides. Their competitive nature, coupled with significant disposable income, makes high-stakes wagering an exciting pastime that complements their high-profile lifestyles.
No, they experience both wins and losses, just like anyone else. The article highlights major wins, such as 50 Cent's $500,000 prize, but also significant losses, like Michael Jordan losing over a million dollars in a single golf bet.
It is often against the rules of their professional leagues. For example, the article mentions the NBA's strict rules and the speculation that Michael Jordan's first retirement was a secret suspension due to his gambling activities.
While several celebrities place large bets, Drake is noted for his particularly high volume of wagering. The article states that his betting activity amounted to a total of one billion dollars in a single year.
Yes, for some it has. Footballer Wayne Rooney admitted to having a troublesome addiction early in his career, and rapper 50 Cent has openly referenced his own struggles with a gambling problem in his music.
