Tom Rawlinson
Mentor
Last updated: 29 April 2024

Throughout history, there have been gamblers who seemed to defy the odds and broke the bank at casinos around the world. Their daring wagers and incredible winning streaks have made them legends in the gambling world. While some lost everything in the end, their stories live on as testimony to the thrilling possibilities that await when Lady Luck is on your side. For a time, these gamblers seemed invincible, pocketing millions and humbling even the most elite casinos. Read on for the inside scoop on some of the most notorious and fascinating gamblers to ever hit the tables.

Akio Kashiwagi

In 1990, Japanese billionaire Akio Kashiwagi was considered one of the biggest gamblers in the world, with a penchant for betting upwards of $10 million a night. Eager to attract high rollers like Kashiwagi and mindful of the local economic landscape, which included discussions about minimum wage reform, Donald Trump purchased several casinos in Atlantic City. When he acquired the casinos, Trump was keen to generate publicity and, despite advice to the contrary, he extended a personal invitation for Kashiwagi to play at his casino.

Kashiwagi sat at a specially roped off table, drawing crowds as he bet $250,000 a hand at baccarat. In just 30 minutes, he was up $500,000. By the end of the first night, he had won $4 million from Trump’s casino. When his winnings topped $6 million, Kashiwagi departed abruptly, to Trump’s fury.

Trump coaxed him back with a special agreement - Kashiwagi would bring $2 million to play and would stay until he either doubled his money or lost it all. After 5 days and $10 million in losses, Trump halted the game. Kashiwagi insisted this was in bad faith and left Trump an IOU for $6 million. The check later bounced.

The unhappy episode signaled demise for both men - Trump’s casinos went bankrupt shortly after, while Kashiwagi was found stabbed to death in Japan. Trump never got his $6 million.

Ed Thorp

Ed Thorp was a college professor with an analytical mind perfectly suited to cracking casino games. During a 1950s Las Vegas vacation, Thorp wondered if blackjack could be beaten using mathematics. His 1962 book, “Beat the Dealer,” demonstrated card counting strategies to shift odds in the player’s favor.

Initially, casinos changed blackjack rules to foil Thorp’s system. But occupancy rates tanked without the classic game, forcing casinos to reinstate the original rules. Thorp’s system was back in play - not that it helped most players. Sound blackjack strategy takes both math smarts and card-counting prowess.

A skilled player himself, Thorp won steadily at blackjack while also pioneering stock market analysis to achieve standout investment returns. He revealed those methods in another bestselling book, proving his statistical genius twice over.

Ed Thorp

Paul Newey

British businessman Paul Newey financed his high roller gambling with profits from high-interest loans. In January 2005, Newey won over £3 million in one night playing roulette - triggering a profit warning from the UK casino.

Newey bet up to £300,000 per spin using a strategy covering all permutations of a single number, effectively gaining 3:1 odds on his £300,000 wager transforming into nearly £1 million.

While Newey relinquished his roulette winnings over the following month, he was sanguine, having lost plenty before. In 2012 he turned to poker but fared poorly - eliminated on day two of the World Series. But for one glorious run, Lady Luck showered Newey in cash.

The MIT Blackjack Team

Bill Kaplan, a professional gambler banned from casinos for card counting, assembled a squad of genius MIT students in the 1990s. Posing as ordinary students, the team stealthily employed card counting and skillful play to siphon cash from Vegas blackjack tables.

At their peak, the group flew to Vegas weekly, departing with bags bulging with six-figure payouts. Kaplan drilled the mathematical concepts and techniques to bend blackjack odds toward the player. As team members graduated, new hotshot students filled their shoes.

Yet like Kaplan before them, casino scrutiny ultimately exposed their card counting ruse, banning them from play. The notorious MIT team raked multiple millions before getting caught - an escapade later fictionalized in the feature film 21. Their system conferred a temporary but very lucrative math-fueled edge over the house. 

The MIT Blackjack Team

If you want to have the chance to break the bank, you can find a list of the top American online casinos. Just remember that tales of epic winning (and losing!) sprees may inspire dreams of hitting a jackpot or destroying casino profit margins, but seasoned gamblers caution beginner's luck rarely lasts long. 

Nevertheless, legends are born when skill, daring and chance collide at the perfect moment. And new legends will rise... one fortunate spin or hand at a time.

Published: 29 April 2024 12:03