Drake knows his way around a casino, there’s no arguing it. You could say we all have Drizzy in awe due to his success in all spheres of life and business, and gambling is no different for the Canadian superstar. The Toronto native turns to gold everything he touches. Acting, music, producing, and now gambling are all his fortes. The eternal bachelor is one of the most popular global artists and one of the few who is not shy to show all facets of his personality.

For Drake, gambling stands high on his lists of priorities. Yes, you could say that it is easy for him to gamble considering his net worth, but it’s not like that. Drizzy is not playing with small sums. As far as high stakes gambling goes, he is one of the top dogs among all celebrities. Whether it is roulette, online slots, or sports betting the Six God is not hiding when things go wrong. He wins big, and he lives with the losses. For a while Drake has lived with the knowledge that the entire world believes that his bets are cursed.

Drake curse was a major Internet meme that went on for a while as few of his major bets have failed to hit the target. Yet, Drizzy didn’t give up. Instead he went in even stronger. Yet, after one of his most recent missteps, for many folks the Drake curse is still well and truly alive. Putting Internet memes aside, Drake has made gambling not only a part of his personality, but also one of his major business ventures. If you’re not aware he is contracted to online crypto casino and sports betting outlet Stake where he serves as an ambassador for the brand.

Celebrities such as Drake are changing the way online casinos are running their business. Being good at what you do is no longer enough. You require a fine representation and Drake fits into that bracket. His contract with Stake is worth somewhere close to $100 million a year, and as a part of it, Drake puts the company’s name in his social media platforms bio, does promotional content to promote the brand, and streams at least once a month his gambling sessions. It is nothing he didn’t do before, and the Drake/Stake partnership is a match made in heaven.

With Drizzy representing one of the biggest crypto casinos on the market, the way celebrities are changing the online casino game is now more evident than ever. Their example is what you would call a jackpot. A bingo! A celebrity that loves to gamble, is passionate about it and about sports and sports betting, and his name rhymes with the name of the casino brand. As we said a heavenly match. It is only a matter of time before other online casinos start to follow suit, as having a high-end celebrity and bonafide superstar as our main representative pays off heavily for Stake despite the hefty contract handed out to the Canadian Rapper.

It is more than interesting to see just how Drake evolution happened in front of our eyes. From a side character in a Canadian TV show, to a musician on the rise, to becoming one of the hardest rapping artists on the scene. Today, Drake is well known as a rapper, lyricist, music producer, with an eye on making his name in acting too, but this time around in Hollywood. On top of that he is one of the biggest gamblers among celebrities. A title he carries with pride we would say. The reason for this is simple; he’s good at it.

You need to lose a bit in order to win. Drake curse is not real, while it was funny seeing people losing their minds over it. Yes, Drizzy did lose a few major bets here and there, and all of them were followed through by the eye of the public. Yet, he’s far from being a loser. With the amount of $1 million bets Drake has made throughout the years, in our eyes he is a winner, both in casinos, in personal life, and in his business ventures. Let’s take a look at his major sports bets.

Maple Leafs Debacle

Drake is super proud of his Canadian origin. You will see him often representing the city of Toronto, the Raptors, and of course the Maple Leafs. The latter ruined his day a month ago. His $1 million bet happened in May, when his hometown Maple Leafs played the Florida Panthers. He was so convinced in the win of the Canadians that he played a $1 million bet on his team. The Maple Leafs lost, but Drake wasn’t too worried about it. While people already started screaming that the Drake Curse is back, Drizzy had a different idea. He said that this time around it is all Justin Bieber’s fault, and that all gamblers now have Bieber Curse on their backs. Justin, another major Canadian superstar, didn’t place a bet, but made a surprise appearance at the Maple Leafs game. Unlike him, the Six God had two bets. $1 million was placed on Toronto’s win whether in regular time, overtime, or on penalties. A second one, a $250 thousand bet was placed on Maple Leafs win by two score difference. Both failed, but only time will tell if Drake Curse is back.

NBA Finals/Stanley Cup

As we said, Drake is a massive hockey and basketball fan. Last year, he showed this affection by betting on both the HL and NBA final matches. It was yet another $1 million bet by Drizzy that backfired. He was rather optimistic so he placed a bet on the Dallas Mavericks beating the Boston Celtics, and on the Edmonton Oilers to beat the Florida Panthers. He was twice failed by Canadian teams, and both times it was against the Florida team. While so far it would appear that Drake Curse is real, as we’re only talking about his losses, it is not like that. Instead, it is about the major wagers Drizzy made, with no regard for odds, betting on his favourite teams and gut feeling.

AFC High and Super Bowl Low

The Canadian Rapper is fond of the most popular American sport, football. As the NFL season closes to its final stage, Drake starts pouring his massive bets in. Each year he goes ballistic during the NFL playoffs. In recent years he took home just slightly over $2 million after his bet hit that Kansas City Chiefs are going to bet then Cincinnati Bengals in the AFC Championship game. It was a $1.1 million bet. The following year, he backed the Chiefs in the final vs. Eagles, wagering close to $950k across few different wagers. The Eagles demolished the Chiefs in a dominant fashion, and none of Drake’s bets went through. He had the Chiefs winning, Mahomes scoring the first touchdown and Kelce being the MVP. None of it materialized.

World Cup Glory

In addition to football, basketball, and hockey, Drizzy likes to wager on soccer too. This was evident during the last World Cup. When the final match came around, Drake had a wager set up. It was another $1 million that was placed on Leo Messi and Argentina. The South American side won the tie, bringing $1.75 million to Drake. Prior to the final many fans were mad that Six God decided to wager on this duel citing their concerns over the Drake curse. To that point Argentina hadn’t lifted the trophy for 36 years while France was looking for a consecutive title. As we said people Drake curse is not real and it can’t hurt you.

NBA Playoffs Income

With Toronto Raptors outside of the playoffs picture, and with finals being far away back in April, Drizzy took his chances on the NBA Playoffs. The game of his choice was the duel between the Los Angeles Lakers, and Minnesota Timberwolves. Drake made an introduction to this game on his social media platforms where he shared a betting slip from Stake showing a $1,026,871.42 payout. He followed it with a caption that was a war cry for Anthony Edwards and it went as follows: ” Lemme see sum Ant.” Edwards delivered as Minnesota won against the Lakers, and he contributed with 29 points.

In addition to all of the sports we’ve listed above and that Drake wagered on, he is also a big fan of MMA and boxing. In recent years many of his bets were tied to UFC and boxing. Back in 2024 he lost $700 thousand betting on Sean Strickland to beat Dricus du Plessis at UFC 297. As his monetary loss was not enough, he was also thanked by Dricus on Twitter as the fighter joked that it was the Drake curse that was what pushed him to a victory. As far as boxing losses goes, Drizzy missed a chance to cash in another $1 million as he was too sure that Fury is going to beat Usyk. That scenario failed to materialize, and Drake was on the losing block once again.

The luck turned its pretty face toward Drake when he recognized that Alex Pereira was on the rise, and covered his win over Jamahal Hill in the UFC 300 main event with an $675,000. It is not easy to keep a track of all of Drake’s bets, as he had quite a few, winning some and losing some. Many news outlets have done the math, and estimate that they have wagered more than $1 billion since joining Stake. Of course not all of it had gone to sports betting as he also enjoys some roulette and slots too. Also, massive wins such as the one where Drake won $3 million when he wagered on McCann to see off Hannah Goldy and Pimblett to beat Jordan Leavitt. If you remember he gifted both fighters a Rolex.

While you could believe that Drake is gambling too much, that’s not the case. Compared to his net worth he is making minor bets. Let’s take a look at it.

Six God Net Worth

As of May, 2025, Drake Net Worth is approximately $250 million. That’s right people, he is a quarter of a billion heavy. For one of the biggest names in the music industry this comes as no surprise. At the end of the day, he is an ex-actor, a celebrity icon, having numerous hits, and sold-out tours. Add to that mix many sponsorship deals, and personal business ventures such as OVO, and you get an idea why Drake has so much money to make $1 million bets. Drizzy is not just a pretty and smiley face. He takes his brand, and his business ventures seriously. Year after year he is churning albums, with each having more than a few platinum releases. His concerts get sold out in a matter of hours, and with his hands in so many businesses that it is hard to count, the money will never stop flowing.

Drake is a brand in his own right and deals he has with Universal Music Group and Stake account for more than a few millions yearly. He is also one of the most streamed artists on Apple Music, Spotify and other streaming services. The royalties from his music only could keep him afloat without too many issues.

With everything above said, it is clear that Drake sees sports betting only as a pastime, and that no matter how many wagers he makes, his net worth is not going to suffer. He is just too big of a brand for it to happen. At the end of the day, he went as far as to serve as a brand ambassador for a sports betting outlet. That is how much he is sure in his bets. The law of probability also states that his luck is bound to change so keep an eye open for the next wager on Drake’s menu.

Source: pexels.com

Celebrities have always played a prominent role in determining market trends. As such, they have become a prominent marketing tool that influences every industry. In the gambling industry, they have significantly impacted the popularity of games and platforms over the years. However, in recent years, celebrities have taken a liking to sweepstakes casinos. These high-profile advertisements allow sweepstakes casinos to leverage exposure to reach wider audiences.

This newfound attention has brought online casino sweepstakes into the mainstream and at the forefront of the gambling industry. These casinos are gaining traction because they allow players to enjoy games without investing real money. They are tools primarily for fun, as they utilize virtual currencies. You can exchange these currencies for cash or other unique prizes. All of this makes sweepstakes casinos attractive by themselves, but let’s explore how celebrities take this a step further.

The Power Of Celebrity Endorsements In Online Casinos

Recommendations from celebrities have historically been the best way to boost brand credibility. The online casino industry perfectly understands this as it has utilized prominent actors, sports icons, and influencers to grow its business. Sweepstakes casinos promote their service primarily through paid sponsorship and social media campaigns. Both play their role in brand exposure and should be utilized together.

Social media has become the main platform for most promotions from celebrities. It has reached this point because of its ability to generate massive interest and click-through rates. For celebrities and athletes, social media is pivotal for the success of endorsements. This is because it is the fastest way to connect with their fanbase and draw their attention. Additionally, these endorsements are a very cost-effective form of marketing, compared to Super Bowl ads.

However, in the modern digital age, the majority of endorsement success lies with social media influencers. Twitch streamers and YouTubers have played the biggest role in making sweepstakes casinos popular. By streaming their gameplay and interacting with interested fans, they engage and compel their audience to play. Fans can visit pages such as casino.online, as a source that has the complete list of new sweepstakes casinos. These are great resources to have in mind as you can quickly assess a sweepstake casino’s most important elements.

Out of all celebrities, influencers have the biggest impact due to the immersive environment they create. Additionally, they best portray the service and give viewers a true insight into the gaming experience. This relatability makes the endorsement more appealing and trustworthy for users, leading to higher conversion rates.

Why Fans Follow Celebrities Into Sweepstakes Casinos

The biggest reason celebrity endorsements are such a powerful tool comes down to the psychology behind their influence. Most fans place their favorite stars on pedestals and wish to emulate their lifestyle. This makes them more likely to follow their endorsements, to support or emulate their idols. Be it a clothing brand of a certain sweepstake casino, fans are more likely to explore the platform themselves if it is endorsed.

One of the key factors behind most successful celebrity endorsements for sweepstakes casinos is exclusivity. This is done through celebrity-themed promotions or giveaways that appeal to the celebrity’s audience. For example, if a certain celebrity favors one game over the others, the promotion will focus on that game. This makes each promotion an exclusive experience that creates a sense of connection with the celebrity for fans.

Celebrities are also enticed to interact with fans and participate in VIP tournaments and other gaming sessions. Additionally, through unique challenges and streams, celebrities can enhance the experience for fans. This generates engagement and fosters a sense of community among fans.

Celebrity-Inspired Sweepstakes Casinos: What’s Next?

As technology evolves, so will the capabilities of celebrity endorsements for sweepstakes casinos. In the current state of the online gaming industry, an upcoming trend is immersive and personalized experiences. With the use of artificial intelligence and other modern technologies, endorsements could be changed forever, allowing players to enjoy unique experiences crafted just for them. Imagine playing games alongside AI-based celebrities as they assist you in your games.

Sweepstakes casinos also have a lot to gain from the blockchain and similar technologies. This is because their inherent benefits perfectly align with the service. They could offer sweepstakes casinos a way to further personalize rewards. Naturally, this also means that it would diversify the pool of withdrawal options for winnings. All of this would be very beneficial to anyone playing at these services.

Overall, the future of sweepstakes casinos is very promising, especially as their systems are optimized. Their timeless appeal will continuously draw in new players and allow them to grow. In turn, this will result in more endorsement opportunities as sweepstakes casinos aim for the top of the gambling industry.

Drake’s high-stakes gambling habit has taken a costly turn. On June 18, the rapper posted an Instagram Story showing over $8 million in losses over the past month at the crypto casino Stake, where he serves as a brand ambassador.

The story, shared with his 142 million followers, revealed jaw-dropping figures, including that Drake wagered $124.5 million in the last 30 days, losing $8.2 million. In the past week alone, he wagered $50.2 million, losing $5.8 million.

He then addressed his followers:

“Gotta share the other side of gambling… Losses are so fried right now. I hope I can post a big win for you all soon cause I’m the only one that has never seen a max these guys max once a week.”

He also shared some recent bets, which include a $200,000 wager on the Oklahoma Thunder to beat the Indiana Pacers by 6-10 points and a $600,000 bet on the Thunder to win straight up on the road.

Drake’s Known For Placing (and Losing) Large Wagers

The June 18 stories are not an isolated incident where Drake posts some of his bets. The rapper is famous for placing substantial amounts, often ending up on the losing end. Some examples of large bets resulting in losses include:

$1.2 million on Jake Paul to beat Tyson Fury in 2023

$1 million on the Toronto Maple Leafs to beat the Florida Panthers

$1 million on Argentina to win the 2022 FIFA World Cup in regular time (they won, but in extra time).

$565,000 on Tyson Fury to beat Oleksandr Usyk

$355,000 bet on Mike Tyson to beat Jake Paul in 2024.

$210,000 on Tyler Fritz to win the US Open in 2024.

Of course, the rapper has also won some sizeable bets. That includes a $1.15 million bet on the Kansas City Chiefs to win Super Bowl LVIII, earning him over $2.3 million.

The “Drake Curse”

Drake’s fortunes have also been associated with more than just his bets. The “Drake Curse” is a long-running online joke suggesting that athletes or teams that Drake publicly supports or endorses lose shortly after.

There are numerous examples of soccer stars, UFC fighters, boxers, and football players taking photos with the rapper and losing afterward. In 2019, Italian soccer club AS Roma even joked that club players are prohibited from posting pictures with Drake.

That said, there have been examples of curse breakers. That includes his hometown Toronto Raptors winning the NBA title in 2019, despite the rapper acting as an ambassador.

Critics Slam Influence and Lack of Transparency

Drake’s photos of betting slips have also sparked considerable criticism surrounding the influence of celebrities and responsible gambling.

Critics argue that his posts show gambling as a get-rich-quick scheme and that his large bets create unrealistic expectations for ordinary followers who do not understand the risks associated.

His posts have also faced scrutiny due to his connection with crypto casino Stake. Critics point out that his posts can lead fans to gamble at the platform, which is illegal in many countries, including the US and, recently, the UK.

His connection to Stake also draws transparency questions. Rumours suggest that his partnership with the platform is worth a nine-figure sum. Also, that Stake at least partly funds his bankroll.

That raises doubts about whether the money he bets is actually his own. Or is he simply playing a role as a high-roller influencer, not affecting his finances?

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Some celebrities love fashion, others collect cars, but a few just can’t stay away from the casino tables. You’ll often find them playing poker, blackjack, or spinning the slots. Some are in it for fun, while others play to win big. Curious about some top celebrities who love playing casino games? We’ve got you covered. Our detailed guide has all the information you need.

Top 6 Celebrities Who Love Gambling in the Casino

Many celebrities are known for often visiting the casino to enjoy games and gamble. While some use online platforms like OMG Casino, others love to head to physical establishments. Below are some of the notable names known for their gambling activities:

1. Tobey Maguire

You probably know Tobey Maguire best as the friendly neighborhood Spider-Man, but behind the scenes, he loves playing casino games.

Maguire was a regular in the underground Hollywood poker scene back in the 2000s and early 2010s. He was a key player in the high-stakes games organized by Molly Bloom. According to insiders and court documents, Maguire wasn’t just participating, he was dominating. Some reports suggest he won millions, often at the expense of other Hollywood elites and Wall Street moguls.

2. Ben Affleck

Ben Affleck is no stranger to the casino floor and unlike many celeb gamblers, he’s not just playing for kicks. He’s a strategic, analytical player with a real love for the game.

Affleck is especially passionate about blackjack, and he’s gotten so good at it that he was banned from playing at the Hard Rock Casino in Las Vegas back in 2014. According to reports, casino staff accused him of card counting during a session.

Affleck has admitted to enjoying high-stakes games and has taken poker seriously too. In fact, he won the 2004 California State Poker Championship, walking away with a prize of $356,400. Not bad for a hobby.

3. Charlie Sheen

It would almost be surprising not to find Charlie Sheen on a list like this. The guy is famous (or infamous) for his wild lifestyle, and gambling has definitely been a part of that. Reports have claimed that at the peak of his addiction, Sheen was spending up to $200,000 a week on gambling.

While he’s not known for being particularly strategic or skilled at gambling, Sheen certainly fits the “notorious” bill. He’s the kind of player who thrives on adrenaline and isn’t afraid to go big.

4. Matt Damon

If you’ve seen Rounders as a poker fan, then you’ve seen Matt Damon play a slick card shark on screen. But it turns out, he doesn’t leave his poker face in the trailer.

Damon developed a strong interest in poker while preparing for his role in Rounders, and the passion stuck. He’s played in numerous celebrity poker events and tournaments over the years, including the World Series of Poker (WSOP).

He’s not quite as intense or as skilled as his buddy Affleck or Tobey Maguire, but Damon holds his own. For him, poker seems to be a mix of fun, strategy, and the occasional high-stakes thrill. Plus, with friends like Affleck and Maguire, he’s had no shortage of high-level competition.

5. Brad Pitt

Brad Pitt doesn’t often make headlines for his gambling habits, but insiders say he’s got a soft spot for the casino floor, especially when it comes to poker and blackjack.

He reportedly fell in love with casino games while filming Ocean’s Eleven and its sequels. Surrounded by real casino settings and professional card players, Pitt began picking up the finer points of the game. Since then, he’s been spotted in casinos around the world, quietly enjoying a few hands without making a big fuss.

Compared to Sheen’s chaos or Maguire’s ruthlessness, Pitt’s more of a low-key high roller. He plays smart, enjoys the atmosphere, and blends in with the crowd.

6. George Clooney

George Clooney takes his love for casinos one step further. Back in the early 2000s, Clooney teamed up with a group of investors to launch a casino in Las Vegas called Las Ramblas. The idea was to create a luxury casino-resort that combined Clooney’s classy image with a world-class gaming experience. Unfortunately, the project fell through, but the effort says a lot about his connection to the gambling world.

Like Pitt, Clooney developed a taste for the casino scene during the Ocean’s film series. While he’s not known for being a regular poker player like Damon or Affleck, he appreciates the casino lifestyle and tried to stake a real claim in it.

Final Thoughts

When celebrities step into casinos, they don’t just play, most of them perform. For some like Tobey Maguire and Ben Affleck, it’s all about strategy and winning. For others like Charlie Sheen, it’s the thrill of the gamble. And then there are guys like Brad Pitt and George Clooney, who bring charm and class to the table.

145 Vietnamese nationals, including government officials, businesspeople, doctors and singers illegally gambled away US$106 million at King Club, a casino operating inside the 5-star Pullman Hotel in Hanoi.

The vast majority of players suffered losses, with total winnings amounting to just 0.22% of the total bets, according to a recent indictment from the Supreme People’s Procuracy.

Inside King Club, an illegal casino at Pullman Hotel, Hanoi. Photo courtesy of the police

The illegal gambling took place between February 4 and June 22, 2024, at the club, which was licensed to serve only foreign visitors with electronic prize games.

Despite this, the venue, run by South Korean national Kim In Sung, secretly catered to Vietnamese gamblers, in violation of national law, which generally prohibits citizens from gambling except under a restricted pilot program.

Authorities identified Kim as the ringleader behind the operation, which masqueraded as a business club. He allegedly organized and managed the activities, pocketing all proceeds, and is believed to have made $9.2 million in illicit earnings.

Of the 145 individuals involved, 136 have been charged for gambling. Most were aware that Vietnamese law prohibits locals from participating in such gambling but chose to do so anyway.

The biggest winner was Nguyen Thanh Bach, a freelance businessman, who won VND2.2 billion over 95 sessions. The smallest winner was Vu Thanh Tung, who played seven times with a total of $5,600 and won $10.

Among the accused are seven officials of Phu Tho Province in northern Vietnam who traveled to Hanoi to gamble.

Ho Dai Dung, former vice chairman of the Phu Tho Provincial People’s Committee, was the most frequent gambler among them. Dung gambled 95 times between February and June, spending over $7 million.

Two singers, Nguyen The Vu and Vu Ngoc Ha, are among the accused. Vu gambled 116 times, playing slots and baccarat, spending $4.3 million in total. Ha, meanwhile, poured $2,600 into baccarat.

Nguyen Van Hung, an employee of hospitality giant Muong Thanh Group, gambled 81 times and spent $531,800.

Another Muong Thanh employee, Truong Xuan Danh, gambled 45 times, with a total amount of $58,700.

Of the nine remaining individuals who have not been prosecuted, one is a staff member at the Central Military Hospital 108 and has been referred to military investigators.

Two who gambled less than VND5 million ($190) face fines, and two others have been deemed mentally unfit. Four individuals are in hiding and are wanted by the police.