An Introduction to the Biggest Sports Betting Losses

Sports betting is incredibly exciting. There is nothing better than the excitement leading up to a well-anticipated event that has the potential to culminate not just in a big win for the team or players involved, but for those who have placed their bets too.

However, over the course of history, there have been a few unfortunate sports betting losses for some. Let’s take a closer look at some of the most unforgettable ones below.

Vegas Dave

Known for being a prominent sports bettor who makes his money off of big bets and long-shot bets, Vegas Dave suffered a $1 million loss in 2016 when he bet on Miesha ‘Cupcake’ Tate at the UFC 200. She was facing off against Amanda Nunes in a battle to retain her title. However, within just three minutes and 16 seconds, Nunes had Cupcake in an overpowering choke, resulting in Cupcake losing the title and Vegas Dave losing his entire wager.

Michael Jordan

Over the course of his career, Michael Jordan has worked his way up to become one of the most iconic NBA players of all time. However, few people are aware of what an avid bettor he once was – and possibly still is. The basketball legend was known for betting up to $100 000 per hole on golf! At one point, it is rumoured that over the course of 10 days, Jordan lost $1.2 million but was able to negotiate his losses down to just $300,000 – still a large figure, but thankfully for him, much less than what he was originally on the hook for.


Hip-hop star Birdman has been a lifelong New England Patriots fan. A proud supporter, he often boasted about the team on social media. At one point, he declared that he was willing to bet $5 million on the team’s performance in the Super Bowl XVVI. One sportsbook called his bluff and invited him to put his money where his mouth is. However, Birdman went quiet and did not take the sportsbook up on their offer. What he did do was place a $1 million bet on a game against rapper 50 Cent. Unfortunately for Birdman, the New York Giants beat his beloved Patriots 21 to 17.

Fast-forward to Super Bowl LII, and Birdman again wagered $100,000 on the Patriots against rapper AR-Ab. This time, the team was defeated by the Philadelphia Eagles, bringing Birdman’s total losses as a Patriots supporter to $1.1 million.

Matthew Webb

This one dates back quite far to 1883. British daredevil Matthew Webb rose to fame when he became the first man to ever swim across the English Channel. He made his living by betting against the public for various swimming challenges. Once he moved to America, he had a few successful challenges, but was quickly running out of money. He invited bets that he could swim across Niagara Falls’ whirlpool. The bet was staked at $10,000, which back then, was a lot of money. However, Webb payed the ultimate price when he entered the water and was never seen again.

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