The High Roller Lifestyle: Stories from the Elite World of Gambling

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The world of high roller casinos is a world where the gambling extravaganza reaches new heights. Although there’s no designated ‘high roller club’ one can join, it’s a community where only real high stakes players can join.

VIP gambling centers around these individuals who are willing to place significant bets at casinos, often reaching seven figures. These high rollers, also known as whales, are enticed by the thrill of sizable wagers and the chance of winning potentially monumental amounts of money.

Some don’t even do it for the money - it’s just they love the thrill and excitement of high roller gambling so much. The high roller casinos, such as the ones you can find at, pamper these players with exclusive privileges such as personalized concierge services, luxurious accommodations and dining, and special bonuses and perks.

In this article, we'll dive into the intriguing universe of high roller casino gambling, exploring the interesting stories from the lives of the elite gamblers, including the story about the music sensation Drake and Oscar-winning actor Ben Affleck.

Drake’s High Roller Antics

Besides being a music sensation, Canadian rapper Drake is notoriously famous for placing enormous sports bets and enjoying high stakes tables on various Las Vegas and Atlantic City casino floors. From his infamous $400,000 bet on Jake Paul to knock down Tommy Fury to his $1 million bet on Argentina to win the World Cup 2022, he has had some fair share of mega sports bets, but the following story is about a night in Atlantic City.

Namely, a few hours after his ‘Aubrey & the Three Migos’ tour show in Philadelphia, Drake reportedly arrived in Atlantic City, where he took it to the hotel’s casino to play a few hands.

The Grammy Award-winning rapper and his entourage were placed in a private high roller area, but luck wasn’t on Drake’s side that night, as he reportedly lost nearly $200,000. However, in typical high roller fashion, Drake will surely come back at the high stakes tables again, but this time with Lady Luck by his side.

Ben Affleck Being ‘Too Good at Blackjack’

Oscar-winning actor Ben Affleck is widely considered to be ‘one of the smartest people in Hollywood’ and a great blackjack player. So good, in fact, that he once got himself banned from Hard Rock Casino in Las Vegas for being too good.

Affleck is no stranger to the high stakes tables. He has been making regular visits in Vegas for years, often winning large sums of money. However, on the night that got him banned from Hard Rock, he won a staggering $1 million by playing blackjack at a high stakes table. Security staff approached him soon after, telling him that he has been accused of card counting - a practice that’s not illegal but can get a player banned.

Besides blackjack, Ben Affleck is also an excellent poker player and has hosted games with fellow celebrities, including his friend Matt Damon and Leonardo DiCaprio. He even won the California State Poker Championship in 2004, netting him around $350,000.

Kerry Packer - The Man Who Casinos Feared Might Bankrupt Them

Kerry Packer was considered one of the most powerful and influential businessmen and media proprietors in Australia in the 20th century. In 2004, his net worth was estimated at around $6.5 billion, but besides his business ventures, he was most famous for his high roller casino sprees.

In 1999, in a span of three days, Packer reportedly lost almost $22 million while playing baccarat - which is still the largest gambling loss in UK history. However, the most interesting high roller story is when Pecker won almost $28 million at the MGM Grand Casino in Las Vegas. Namely, he was playing up to seven blackjack tables at once, and he asked the casino to lift the high roller limit of $500,000 per hand.

The casino did so, and with luck by his side, Packer won almost $26 million. Legend has it that as much as casinos wanted a ‘whale’ as Packer to play at their tables, they feared that his high roller style might bankrupt them if he gets on a winning streak.

- B.E. Delmer,

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