When the Chips Are Down: Celebrities Who Love to Gamble
Photo by Kaysha

Sometimes, looking only into our own lives can be quite boring, we need a sneak peek of other lives too. People usually look down on such snooping into the lives of other people, yet we embrace reading books and watching good TV shows. Which usually revolve around the lives of other people and taking a deep dive into their predicaments. Of course, snooping around other people’s private life when the boundaries are set is purely wrong.

However, if people choose to be open about their lives and share them with others, why not take a closer look? A lot of celebrities are open about what they are doing, and they share that with their followers to see. Thus, it is no wonder that we know so much about them, especially about some peculiar things they do. A lot of celebrities like to gamble in their free time, let’s take a look at some of them and see what they are up to.

Maha Vajiralongkorn

People usually associate gambling with either the lowest a man can get or as a purely hedonistic lifestyle of the rich. Well, many are not aware that a lot of people in power are gambling addicts just like many other regular people. Maha Vajiralongkorn, the current monarch of Thailand, is living a hedonistic lifestyle. Even though he is a king, who has a lot of very specific beliefs and runs his country in a specific manner, he likes to gamble in his spare time.

Of course, the rich can’t just go to any casino and gamble there, many of them are preferring the online ways now. If you take a look at the 20 best Thai lottery websites, you will see there is a lot to choose from, all within government guidelines. Whether you are an inbred king looking for some fun or just want to test your luck, getting an online lottery ticket could be the way to go.

Donald Trump

Speaking of influential people that are gamblers, up next is none other than Donald Trump. Everyone knows the guy, the first US president not only to get impeached twice but also the first US president to get indicted. He made a lot of money over the years, but he would have made even more if he didn’t spend it in casinos. How he led the country does speak about his issues with responsibility and his rash decisions.

Donald Trump likes to gamble, but he also likes making other people gamble by making casinos. Unfortunately for him and many others, he was not good at running casinos, which led to bankruptcy. The long-overhyped Atlantic City with the infamous Trump Taj Mahal was bankrupted due to many poor decisions. This goes to show that life really is a gamble, especially when you make irresponsible decisions in life.

Brad Pitt

Brad Pitt is known for his very successful acting career, but he is not as successful at gambling. Actors have to convey emotion in their roles, and they have to make characters feel authentic. In order to do this, many actors, including Brad Pitt, want to feel what their characters feel. In this example, Brad Pitt had to get ready for his role in the Ocean’s franchise, a popular series of heist films.

In order to get ready for gambling and casino scenes, Brad Pitt went to real casinos and played a few games. What started out as just research for the movie, turned into a habit he picked up after the movie was shot. When you are as rich as people on this list, losing money on gambling is no longer a big problem. This allows them to continue playing and indulge in these forbidden delights of gambling.

Matt Damon

Matt Damon follows a pretty similar route that Brad Pitt followed, he was not into gambling before his acting career. However, this changed after shooting a hugely popular movie, Rounders, released in 1998. This just goes to show that gambling is something that is very hard to resist, no matter what type of person you are. Even after thousands of years, a lot of people think that they will be able to resist the temptations of gambling.

They think they are different and special, but that is what everyone thinks before they continue to gamble for years to come. Matt Damon is no exception to this rule as he continued playing and he is now one of the top poker players. Even though he might be able to beat you in a game of poker, he can’t beat his urge to continue playing poker.

Floyd Mayweather

Usually, it is the battles that we fight against us that are the hardest ones to beat. It is the problems inside us that we actually fight even when we are fighting against other things in life. Even though Floy Mayweather has beaten a lot of opponents in the ring, there is one opponent that keeps getting the best of him. Floyd spoke about this issue and stated that he even got into gambling when he was just a kid.

These problems are usually rooted deep within the subconscious and they are greatly influenced by the environment. This is why so many celebrities end up gambling, they have a lot of issues on their own, but money is not the issue. When money is not the issue, they will try anything they can do to solve other problems by using money. Whether that is gambling away your money on casino games, or some other harmful coping mechanisms. 

50 Cent

A lot of rappers these days are just posers that just share the rap lifestyle but do not live it. However, there are many rappers that stay true to their beliefs, the good ones, and the ugly ones. Among the ugly things, the rapper lifestyle can’t be separated from gambling. 50 Cent is among the rappers who just can’t get over gambling and keeps making big bets publicly. 

Whether it’s about other celebrities that have gambling problems, such as Floyd Mayweather, or major events, 50 Cent keeps making big bets. These bets are not made just to make money off them, they are made to spread the word around. Even if 50 Cent loses the bet and the money, he still gets a lot of people talking about him which drives his popularity and image.


Even though Drake wants you to believe that he is a good boy, he really is not that different compared to other rappers. A good example would be how Drake treats women, a confirmed case of his lies. Even though he promotes young fans to respect women, he really hasn’t shown respect in many songs not just to women, but also to his underaged fans. This aside, he also hasn’t been able to separate himself from the gambling part of his life.

The latest iteration of his gambling problem was seen live over at Twitch when he was sponsored by Stake. You would imagine that if you have money, you would use it to do something good in this world, or at least not use it to harm others. However, promoting gambling when you are already filthy rich is a very interesting low point that we will discuss later on.


Another big name that many will recognize, Jay-Z, is on a whole other level of enjoying gambling. For almost a decade, one of Jay-Z’s goals is to make a gambling empire, specifically in New York. As stated in his song featuring Alicia Keys, in New York, there is nothing you can’t do. The big lights will inspire you, and these big lights sure inspired Jay-Z to chase a casino license in NYC.

He is already a billionaire, and he says that he isn’t doing this for the money, but for something much grander. Jay-Z says that you can impress your business partners with a nice casino club and use it for parties. Now, whether being a poser and people pleaser or just a liar is worse, you be the judge of that.


xQc (Félix Lengyel) is one of the most popular streamers on Twitch, known to cater to a big audience, especially minors. Whether someone chooses to gamble or not is their choice, but as with many other choices, you should not force them on other people. Although xQc never forced someone to gamble, he was well aware of to whom he was showing his gambling-sponsored streams.

Drake was not the only one who was paid by Stake to promote gambling, many Twitch streamers were. There are a lot of kids on Twitch and kids have very moldable brains and ways of thinking. When they see their idols doing something and making it look fun, they are bound to try that for themselves. This makes xQc not only a big celebrity who likes to gamble but also one that promotes it to a wide audience.

Adin Ross

This name keeps popping up a lot lately for many reasons, and his love for gambling is one of them. Adin Ross just keeps getting himself in trouble after trouble, which is highly profitable for him, just like gambling is. He started streaming on Twitch, and he was on the bandwagon of gambling live on a rigged account that wins more than it loses. Adin Ross was banned multiple times which led eventually to a permanent ban, but not for gambling.

He was banned for violating hate speech policies on multiple occasions and encouraging hate speech within his community. Something his new best friend, Andre Tate, knows a lot about and encourages hate in this world. However, Adin is able to continue with his mischief, and gambling, on Kick, a new streaming service founded by Stake. He continues playing slots, but he is showing a lot of character development lately, but time will tell if that is only an act or genuine progress.

Tiger Woods

In life, rarely do we have only one problem, they usually come with a bonus, an additional problem that we do not want. Tiger Woods was blessed with great golfing skills, no one can deny that, but with that, he was cursed with making bad decisions. He is becoming known not just for his golfing, but also for his many affairs which were a public secret for some time.

It was not until his wife saw the affair for herself which erupted the avalanche of his adultery. However, his gambling problems were known for much longer, and they are still known to this day. However, just like all the other celebrities on this list, he is just another rich and influential man who can do whatever he wants because he is rich.

Michael Jordan

Even top athletes can’t resist gambling and Michael Jordan proves this. The old Greek said that with a strong body comes a strong mind, but it looks like this mind still can’t resist gambling. In sports, you need skills to succeed, but you also need luck, every athlete knows the importance of luck in sports. However, luck is not something you can control, it is either there or it is not there, and Michael Jordan knows this both from his sports and gambling careers. 

As a great leader once said, power is what attracts the worst and corrupts the best, something all these celebrities can attest to. If someone has billions of dollars that they do not spend on making this world a better place, they have a serious problem. In the US, there is a problem that these people are not looked down upon, in fact, they are worshiped. People look up to these celebrities, even if they know about the bad things they are doing.

This fetishization of such behavior has become normal, it is weirder if you actually question it. But hey, discussing the morality of this behavior is not included in this article meant to show you the celebrities who love to gamble. It is important to talk about these subjects and spread the word around if we really want to make a change. Whether it is making systemic changes or changes of perspective, these things can only be changed by spreading the word around.

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