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Drake, Michael Jordan & Ben Affleck: The World of Celebrity High Rollers

| Staff Report |

The term high roller is widely used in the world of casino gambling and sports betting, it describes individuals who like to wager significant amounts of cash in the pursuit of increased gains.

In the virtual realm, there’s even online casinos that specialise in accommodating high rollers, whether they operate generous VIP schemes for such players or operate table games with increased betting limits.

You can check out Time2play’s recommendations for the best high roller casinos, enabling you to enjoy the best possible experience and get the best bang for your buck!

But who are the world’s most famous high rollers? In this post, we’ll take a peek into the fascinating realm of high spending celebrity gamblers!

#1. Ben Affleck

Where else but to start with Hollywood superstar Ben Affleck, who’s best known for blockbuster hits like Good Will Hunting (which he co-penned himself), Pearl Harbour, as well as lesser known movies such as Mallrats and Surviving Christmas.

He’s also something of a big shot in the world of celebrity gambling, having become a regular feature at tournaments such as the Commerce Casino’s California State Poker Championship since 2014.

In his debut at this tournament, he superbly beat 90 other competitors and took home a first prize of $356,400, which is not to be sniffed at even for a mega-rich Hollywood actor!

Interestingly, one of the players who lost to Affleck was the professional poker star Stan Goldstein, and in some respects, the actor has become a respected gambler who’s considered to boast considerable skill and a strategic mind.

During his gambling career that has extended for more than a decade, Affleck has won millions of dollars and continually beat respected and professional players. This makes him something of an anomaly in the celebrity circuit, as many famous high rollers are renowned for losing more than they win!

On a final note, online casinos in the US are known to look for and analyse Affleck’s effective poker winning strategies, with this particular card game a particularly skilful endeavour for the actor!

#2. Michael Jordan

By acclamation, Michael Jordan is the single greatest basketball player of all-time, having played 15 stellar seasons in the NBA and won six Championships during this time.

He also won 6 NBA Finals MVP awards, with the 14-time All Star becoming a true cultural icon in the process.

It’s also no secret that the brilliant Jordan likes to gamble and bet on a regular basis, with the man himself having been candid about his wagering activity through the years.

This should come as a surprise given Jordan’s competitive nature, while the former superstar’s virtually unlimited fortune also helped him to gamble freely.

According to some reports, Jordan once lost a staggering $5 million in a single craps session in Las Vegas, while it has also been suggested that his son has incurred some heavy losses during gambling sessions in Sin City.

These losses were incurred after Marcus Jordan hosted a lavish Vegas party, during which time some $35,000 was spent on gambling alone.

Sure, this is small fry when compared to his father, but he has clearly inherited the great man’s competitive outlook and penchant for on and offline gambling.

#3. Drake

While some have suggested that Canadian rapper Drake’ recent album ‘Honestly, Nevermind’ lacks the zest of the artist’s former work, it continues to sell well and has extended the career of one of the world’s most prominent musicians.

But did you know that Drake is also an avid gambler? Well, the rapper’s betting activity has been the subject of some scrutiny of late, with sources alleging that he once wagered in excess of $1 billion in two months.

Drake has had some notable wins in his gambling career. One of the most notable was his wagers on a UFC London event where he backed Molly McCann and Paddy Pimblett to win their respective bouts. His stake of $2,296,211.30 earned him a cool payout of $3,723,077 and won each of the fighters new Rolex watches in return. 

He has also lost a total of $26.8 million, with the rapper particularly active when wagering on popular American leagues such as the NFL, the NBA and international sports like Formula 1 and the Ultimate Fighting Championship (UFC).

Of course, Drake can afford to sustain significant losses alongside the occasional, high stakes win, as he currently has an estimated net worth of $250 million.

It’s also suggested that Drake is a fan of casino gambling and iterations of roulette, meaning that he wagers across a broad range of verticals and likes to spend his money on markets that are driven by both skill and chance.

Photo from Deposit Photos

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