Strangest Betting Props That Won – When Things Are Super Lucky!
Posted: January 15, 2025
Updated: January 15, 2025
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How do you bet on particular things?
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Sometimes the underdog can win
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The strangest betting props that won

Uncover the wildest tales of risk-taking with the strangest betting props that won. These bizarre bets, ranging from presidential surprises to pop culture shocks, redefine the boundaries of gambling. Explore the stories behind these unique betting markets, and discover how the unexpected can turn into life-changing victories.
Betting thrives on unpredictability, and these stories prove that truth is often stranger than fiction. The strangest betting props that won aren’t just about money, they’re about taking risks and defying expectations. From political shocks to pop culture surprises, these wagers highlight the thrill of gambling in all its forms. Betting has always captured the imagination of people around the world.
While traditional bets focus on sports or politics, some gambling props are so unusual they defy logic. These strange bets started as jokes or absurd possibilities but ended up becoming reality. These stories show how unpredictable the world can be and why betting remains so fascinating. Register at any of the online sportsbook sites in Canada for the widest array of betting markets today!
Trump’s Victories – Strangest Betting Props That Won
Trump won the US presidential election this year, and once more, many won bets on his unexpected victories. Also, Donald Trump’s 2016 U.S. presidential election win stunned the world. Many saw his candidacy as a publicity stunt. However, one man in the UK took a chance, betting that Trump would not only run but also win. His bold prediction became one of the strangest betting props that won. The world was skeptical, but as Trump climbed the polls, the wager started gaining attention.
What made this bet so unusual was its improbability. Trump, a businessman and reality TV star, had no prior political experience. Experts dismissed his chances, focusing instead on career politicians. Yet, this bettor saw an opportunity in what others called impossible. As the election results rolled in, disbelief turned into astonishment. Trump’s win wasn’t just a political shock, it was a gambling phenomenon. Register at 22BET Sportsbook for similarly shocking markets!
David Hasselhoff’s Rehab
Among the strangest betting props that won, we could cherry-pick many celebrities. David Hasselhoff, the star of Baywatch, became the center of a strange betting proposition. The bet revolved around whether or not he would enter rehab by a certain date. While such wagers may seem invasive, they highlight society’s fascination with celebrity culture. This particular bet gained traction on online forums, sparking heated discussions about Hasselhoff’s personal life. In the mid-2000s, Hasselhoff was struggling publicly.
His issues made headlines, and fans speculated about his next steps. Amid this chaos, someone placed a bet that Hasselhoff would indeed check into rehab. Many dismissed the idea as a cruel joke, but the bettor remained confident. Soon enough, the news broke: Hasselhoff had entered rehab, turning this strange bet into a winning one. According to Reddit, several users seem to have won a bet on whether he will go to rehab or not. Thus, it seems celebrity props can be valuable too!
Leaked Plots – Strangest Betting Props That Won
Television spoilers have always sparked intense debates online. However, betting on leaked plots takes this obsession to a new level. In 2019, rumors about the final season of Game of Thrones created one of the strangest betting props that won. Fans placed wagers on everything from character deaths to the Iron Throne’s successor. One bettor stood out by correctly predicting several major twists. Many accused them of having insider knowledge, but no evidence surfaced.
Their bet hinged on one specific leak, which outlined the show’s controversial ending. As the episodes aired, it became clear the leak was accurate. The bettor walked away with a massive payout, leaving others baffled by their foresight. According to Hobby Lark, people used to place strange bets between each other. This became rather boring quickly, as people could ensure their victories. But how about story plots? When you receive leaked plots, you can easily bet on story wagers.
Rory Mcilroy’s Victory
Underdog athletes such as Lewis Hamilton or Rory Mcilroy were all forming some of the strangest betting props that won. In the world of sports, Rory McIlroy’s success seemed inevitable. However, one bet on his career stands out as particularly strange. A father placed a wager when McIlroy was just 15 years old. He bet that his son would win the Open Championship by age 25. This long-term bet wasn’t just about faith, it was about seeing potential others might miss. McIlroy’s journey to greatness wasn’t without challenges. Injuries, setbacks, and fierce competition made his path uncertain.
Yet, his father’s belief never wavered. When McIlroy won the Open Championship at 25, the bet became one of the strangest betting props that won. It wasn’t just a financial victory, it was a moment of validation for a proud parent. According to CBS News, Rory Mcilroy’s father won almost a fortune by simply trusting his son, who was an underdog in the competition.
Kanye’s Breakup – Strangest Betting Props That Won
Kanye West’s personal life has always been a topic of intense speculation. However, betting on his relationships takes this fascination to a new level. In 2021, rumors swirled about Kanye’s marriage to Kim Kardashian. Someone decided to bet on their breakup, turning gossip into a gamble. The bet gained attention as the couple’s relationship appeared to unravel. While some called it tasteless, others saw it as a bold prediction. When the news of their divorce broke, the bettor emerged victorious.
The payout wasn’t just financial, it was a moment of vindication for those who thrive on taking risks. This story highlights the fine line between entertainment and ethics. Betting on personal lives can feel intrusive, yet it reflects our culture’s obsession with celebrity drama. We have written a whole Kanye West betting guide to learn how to bet on celebrities and their absurd decisions.
You Can Even Bet On DBCooper!
The mystery of D.B. Cooper has fascinated people for decades. This unidentified man famously hijacked a plane in 1971, escaping with $200,000 in ransom money. Despite countless theories, his identity remains unknown. Unsurprisingly, someone decided to bet on solving the mystery. The bet centered on whether Cooper’s identity would be revealed by a certain date. While the odds seemed slim, one gambler took the chance. In a shocking twist, a credible lead emerged, pointing to a potential suspect.
While this didn’t confirm Cooper’s identity, it reignited public interest in the case. For the better, this development was enough to secure a payout. What makes this story unique is its blend of history and speculation. You can take a look at some of the most recent DB Cooper identity odds too! These are all among the strangest betting props that won. Register at 22BET Sportsbook to find similar markets today!