7 Crazy Prop Bet Wins That Paid Big

Man Holding His Head in Disbelief in Front of a Bunch of Hundred Dollar Bills

Prop bets typically aren’t the bread and butter for most successful gamblers. That isn’t to say that there’s no money to be made in this arena, but most gamblers consider prop bets to be more of a novelty than anything else. Prop bets exist in areas you wouldn’t think, including news, politics, and of course, sports.

Because there’s no real precedent or hard data to rely on for many of these bets, it can seem like oddsmakers throw out arbitrary numbers, hoping that it will result in a win for the house. From the merely unlikely to the straight-up bizarre, I’ve put together a list of the 10 craziest prop bet wins.

1 – Lie Detector

The thing about making money is that it doesn’t care about your political preferences. While that might be true, Donald Trump still helped bettors beat the books when he gave his primetime address in January of 2019.

Various sportsbooks offered a variety of prop bets including whether or not Trump would declare a state of emergency at the border, how long the speech would take, and the color of his famously-long ties. In the end, it was a different bet that cost one sportsbook.

The bet they offered focused on the amount of lies (as determined by the Washington Post Fact Checker) that he would tell during his speech. The over/under was 3.5, and nearly 92% of bettors took the over. The result? The book ended up paying out more than $275k when it was all said and done.

2 – Winning Bites

Luis Suarez isn’t only known for his footwork on the soccer field, he’s developed somewhat of a reputation as a biter.

A Norway gambling website decided that it would be funny to offer a prop bet giving 175-1 odds that Suarez would bite someone during the 2014 World Cup. Coming off two previous on-field bites, these odds seemed like a decent value for bettors.

Soccer Player Luis Suarez Laying on Field

Of course, dozens of gamblers jumped at the opportunity to get in on the comedic action (167 to be exact). After biting an Italian opponent, our 167 lucky winners cashed in! The largest win was just over $3,000, but the story is priceless.

3 – Safety First

Of all the ways to put points on the board in an NFL game, a safety is the most unlikely to occur. In fact, there had only been seven safeties in Super Bowl history when John R. put down $1,000 on a prop bet that required a safety to be the first score of the game.

At 50-1 odds (other books had up to 75-1 odds), his reasoning was may have been questionable… But, in a lucky event, it paid off!

Tom Brady’s intentional grounding in the end zone resulted in a $50,000 payday for John, and his risky $1,000 wager was rewarded.

4 – Pats Parlay

The Super Bowl is renowned amongst gamblers for their long list of obscure prop bets. Although this particular bet wasn’t necessarily strange, it had nearly zero chance of hitting. Okay, it had a 565-1 chance.

The game was Super Bowl LIII, and the bet went like this… A parlay with two parts—Tom Brady needed to throw an interception on his first pass of the game and there had to be zero touchdowns scored in the first half. Since the bet was a parlay, both parts had to win in order for our bettor, Nate, to cash in on his $2 wager.

Football Player Tom Brady Throwing a Football

Against all odds, Tom Brady threw an interception, and neither team was able to get the ball in the end zone in the first half. A $2 bet netted $1,131.58 and one fan who didn’t care about the lack of offense. You could say that this was one crazy parley betting win.

5 – Don’t Call It a Comeback

If you thought the Patriots legendary Super Bowl comeback against the Falcons was impressive, take a seat for this one.

In the Mali vs. Angola soccer match during the African Cup of Nations in 2010, Mali trailed 4-0 with just over 15 minutes left to play in the game. For some reason that is still hard to fathom, one bettor placed a USD $6.34 wager on Mali making a seemingly-impossible comeback to tie or win the contest.

Two Soccer Players Battling for Field Position

During the next 15 minutes of game time, the unthinkable happened. Mali found the back of the net in the 78th minute, then again in minute 88. Still, with a 4-2 score heading into injury time, things seemed pretty well wrapped up. But two more goals by Mali in the 93rd and 94th minute resulted in a 4-4 draw and a USD $6,300 win for one lucky fan.

6 – The Long Shot

I’m not one to place much stock in the supernatural, especially when it comes to risking money. But the same cannot be said about soccer fan Adrian Hayward.

The story goes that he had a dream in which Liverpool player Xabi Alonso scored from behind midfield. Most people would wake up and go about their lives, but not Adrian. Shortly after his dream, he walked into a bookmaker and convinced them to let him wager on the unlikely goal happening in real life.

When the bookmaker stopped laughing (I’m assuming), he allowed Mr. Hayward to place a USD $250 bet at 125-1 odds that it would happen before the end of the season.

What happened next might make you wish you remembered all the dreams you forgot.

With Liverpool up in the game, their opponent Luton sent their goalkeeper downfield to help out the offense. None other than Xabi Alonso got the ball, saw the open net, and scored from his own side of the field. The goal earned Adrian Hayward more than USD $31,000.

7 – The Blowout

Brazil has a storied past as a soccer nation. This made their 7-1 defeat in the 2014 World Cup a surprise to many. Nobody could have predicted such a large margin of victory for the German squad…except one fan.

Not only did the unnamed bettor place money on Germany winning, but the wager was on a 7-1 win specifically. Additionally, he needed Sami Khedira of Germany to score a goal in the rout. What were the odds for such an unlikely confluence of occurrences? The $20 bet was placed at 2,319-1 odds. The payout for the unforgettable win ended up being $46,000.


If you find the types of bets included in this article appealing, get familiar with all the basics of prop bets. From the mundane plays like which team will score first, to the crazy bets regarding player behavior, there’s no shortage of options when searching for props.

While it’s true that the results I’ve written about in this article are extremely rare, there’s no denying the fun appeal of a low-risk, high-reward wager on an unlikely event happening during the course of a game, race, or political campaign. Perhaps your next dream will give you the keys to the perfect prop bet, and maybe you’ll be featured on the next list.