December 17, 2025 2 min read

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Gambler Loses $25,000 Trying to Win $25 After Unexpected Comeback

Betting big on a sure-thing is an even worse strategy than placing thousands of dollars on your favorite team when they are "bound" to win

Rookie gamblers often wonder about odds – they argue that you can bet on that terrible moneyline and, if you have enough money going, you will get something out of the action in the end.

But what happens when you gamble $25,000 to win just $25 on a “sure thing” and that thing comes up short? 

You Put on a Brave Face and Carry On

This is precisely what happened to one gambler who placed the wager on Polymarket, a prediction market platform, backing the Pittsburgh Penguins to take out the San Jose Sharks in what was a guaranteed win, more or less. 

The Sharks, though, ended up coming on top in a little expected upset that saw them surge to a narrowly-clipped victory at 6-5. The gambler, who used an anonymous X account, was not really all that upset about the loss, arguing that next time, some incredibly long odds would turn a profit and things would even out.

Be that as it may, the logic of placing a $25,000 bet to win only $25 seems self-defeating and not founded in common gambling interest. While there is an argument to be made for backing your favorite team, $25,000 just seems a little excessive.

Journalist

Jerome brings a wealth of journalistic experience within the iGaming sector. His interest in the industry began after graduating from college, where he regularly participated in local poker tournaments. This exposure led him to the growing popularity of online poker and casino rooms. Jerome now channels all the knowledge he's accrued to fuel his passion for journalism, providing our team with the latest scoops online.

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