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The Most Heart Breaking Sports Betting Losing Streaks

Sports betting can be an incredibly exciting and lucrative hobby for many people, but with the potential for huge rewards comes the risk of devastating losses. For some unfortunate individuals, sports betting has become a heartbreaking cycle of losses, with each defeat more crushing than the last.

Here are some of the most heart breaking sports betting losing streaks that have ever been documented.

One – Terry Ramsden (The British Businessman)

One of the most infamous losing streaks in sports betting history belongs to Terry Ramsden, a British businessman who became addicted to horse racing betting in the 1980s. Despite starting out with a fortune of £15 million, Ramsden’s losses quickly spiraled out of control, leading him to borrow millions from banks and loan sharks to fund his habit. Over the course of just two years, Ramsden lost an estimated £30 million, leaving him bankrupt and facing a 21-month prison sentence for fraud.

Two – Akio Kashiwagi (The Japanese Businessman)

Another tragic example of a sports betting losing streak is that of Akio Kashiwagi, a Japanese businessman who became known as the “Taj Mahal Whale” due to his habit of betting millions of dollars on baccarat at the famous Taj Mahal casino in Atlantic City. Kashiwagi was initially successful, winning more than $6 million in just one week, but his luck quickly turned. In 1992, he lost a staggering $10 million in a single night, and by the time of his death in 1992, he had lost a total of $200 million on his baccarat bets.

Three – The Man named Pete

Perhaps the most heart breaking sports betting losing streak, however, is that of a man known only as “Pete.” In a post on Reddit in 2016, Pete revealed that he had been a compulsive sports bettor for more than a decade, and had lost an estimated $1.2 million during that time. Despite trying to quit several times, he always found himself drawn back to the thrill of gambling, and his losses continued to mount. In his post, Pete described the devastating toll that his habit had taken on his life, including the loss of his marriage, his job, and his home.

Four – The “Miracle on Ice” Game

The 1980 Winter Olympics in Lake Placid, New York, featured a game between the United States and the Soviet Union that has gone down in history as the “Miracle on Ice.” The U.S. team, made up of amateur and college players, was considered a huge underdog against the powerful Soviet squad. However, to the amazement of the world, the Americans pulled off a stunning upset, winning 4-3 in a game that has been called one of the greatest moments in sports history.

But for one bettor, the outcome was devastating. A man from Las Vegas had bet $50,000 on the Soviet Union to win, at odds of 10-1. When the Americans pulled off the upset, he lost $500,000, a devastating blow that left him reeling.

Five – The Cleveland Browns’ 0-16 Season

In 2017, the Cleveland Browns became only the second team in NFL history to go winless in a 16-game season. For fans of the team, it was a year of frustration and disappointment, as they watched their beloved Browns lose game after game, often in heartbreaking fashion.

But for one bettor, the season was a disaster. He had placed a $100,000 bet on the Browns to win at least one game that season, at odds of 50-1. When the Browns went 0-16, he lost his entire bet, a crushing blow that left him emotionally and financially drained.

Six – The Boston Red Sox’s 2004 ALCS Comeback

In 2004, the Boston Red Sox were down three games to none in the American League Championship Series against their bitter rivals, the New York Yankees. No team in baseball history had ever come back from such a deficit to win a seven-game series.

But the Red Sox did the impossible, winning four straight games to take the series and advance to the World Series. For fans of the team, it was a moment of euphoria and joy, as they celebrated their team’s incredible comeback.

But for one bettor, it was a nightmare. He had bet $100,000 on the Yankees to win the series, at odds of 2-1. When the Red Sox completed their comeback, he lost his entire bet, a crushing blow that left him feeling empty and defeated.

Seven – The Chicago Cubs’ 108-Year Drought

For more than a century, the Chicago Cubs were one of the most cursed teams in sports. They had not won a World Series since 1908, and fans of the team had endured decades of heartbreak and disappointment.

Not until the year 2016, the Cubs finally broke their drought, winning the World Series in dramatic fashion. For fans of the team, it was a moment of pure joy and elation, as they celebrated their team’s incredible accomplishment.

But for one bettor, it was a different story. He had bet $50,000 on the Cubs to never win a World Series again, at odds of 1,000-1. When the Cubs broke their curse and won the championship, he lost his entire bet, a crushing blow that left him feeling hollow and defeated.


These are just a few examples of the devastating impact that sports betting losing streaks can have on individuals and their families. While some people may be able to enjoy sports betting as a harmless pastime, for others it can quickly become an all-consuming addiction. If you or someone you know is struggling with a sports betting problem, it is important to seek help as soon as possible to avoid a similar fate.

Written by Punters Digest

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