The Most Famous Betting Losers of All Time

The Most Famous Betting Losers of All Time

While the sports betting world is full of daredevils, who are always confident in their predictions, they have all experienced crushing losses. When it comes to the most experienced gamblers with massive fortunes, their losing bets can reach hundreds of thousands or millions of dollars. In this article, we will tell you about such passionate bettors and events that cost them a lot.

Michael Jordan

The basketball legend, who is widely regarded as the best NBA player of all time, approaches every aspect of his life in a highly competitive manner. That is why it is not surprising that Michael bets on everything imaginable, including golf matches. Since Jordan was betting $100 000 per hole on average, he could lose a significant amount quite easily. This is exactly what happened during one of these friendly golf tournaments when Michael lost $1.2 million.

David Oancea

Unlike the previous gambler, David Oancea is not a world-famous individual. However, the sports betting community recognizes David as a respected bettor and calls him Vegas Dave. His unsuccessful bet was dedicated to the UFC 200 fight between Miesha ‘Cupcake’ Tate and Amanda Nunes. Dave was sure that Tate would be able to dictate the fight and defend her title. However, it took Nunes just over three minutes to choke Miesha and deprive the bettor of $1 million.

Brit Bets

This bettor has not faced such crazy losses as previous gamblers. But at the same time, experienced bettors often discuss stories about his wins and losses. One such story happened in 2013 when Brit made a £10 parlay bet on 12 rugby matches and won £38 970. Encouraged by his luck, he decided to place another bet on the game between Australia and Wales. But this time around, Brit bet £30 000 on Wales. Had his prediction been right, he would have received £55 000 on top of his bet. However, Australia prevailed and prevented Bets from enjoying his lucky week to the fullest.

Matthew Webb

Not all of the greatest betting losses revolve around money. Matthew was a famous gambler and daredevil in the late 19th century. Webb became the first to swim across the English Channel. He overcame complex swimming challenges regularly to make a living but he did not have enough money. So, Matthew traveled to the United States to find new betting opportunities. And in 1883, one such bet proved fatal to the gambler as he decided to swim across the Niagara Falls whirlpool for $10 000. After this absurd challenge, no one ever saw Webb.


This established American rapper has never hidden his betting habits. Instead, he has often been outspoken about his crazy sports betting on social media. Being a passionate New England Patriots fan, Birdman made a $1 million bet on this team against 50 Cent before the Super Bowl XLVI. As a result, 50 Cent got his money and taught Birdman a costly betting lesson.

GBC Time

GBC Time