When it comes to betting, people will bet on just about anything, and I don’t mean at the tables or machines. Literally, if they are real high-rollers, serious gamblers will bet on ANYTHING.

There have been some crazy bets made in gambling history, but some of them simply need someone to take the time to talk about them. Certainly, proposition bets, or prop bets for short, have become exceedingly popular with people betting on strange sports occurrences, celebrity baby names, and the queen of England’s hat color. This little top 5 list includes both casino bets and wacky prop bets that are pretty funny to read about. Not all of them ended up well for the bettors, nevertheless, they are still entertaining material for a few laughs.

#5: The Diet Cheating Bet

Poker players have a hard life. There is a slight bit of sarcasm and a little more matter-of-factuality in that comment. It most certainly is not too tough to have to play at prestigious casinos, sitting all day while gorgeous girls serve you drinks. Conversely, it is hard on one’s health. Leading such a sedentary lifestyle is what led multi-time WOSP champion Howard Lederer down a path of morbid obesity. Doctors told him that he would die within a few short years if he didn’t change his diet. After gastric bypass surgery and becoming a vegan that exercised regularly, Howard became healthy again. Then, a fellow professional poker player bet him as a joke that he wouldn’t eat a cheeseburger. Lederer proceeded to inhale the burger, collect his money, and then went back to his diet.

#4: The Skylab Wreckage Bet

In 1979 owner of the El Cortez Hotel and Casino Jackie Gaughan decided to start taking bets on where the wreckage of the Skylab space station would land when it re-entered the atmosphere. Jackie laid odds on anything and everything, including the El Cortez itself, but the space station’s final crash site ended up being in Australia.

#3: The Male Breast Implants Bet

This one is quite ridiculous and took a lot of courage. Brian Zembic and a friend of his got into an argument over breast implants. A challenge stemmed from that: get 38C breast implants and keep them in for a year for $100,000. Oddly enough, Zembic took the bet and went under to cover previous gambling losses. Even weirder, after the year was up and he had collected his winnings, he kept the implants in as a conversation piece.

#2: The “Rain Man” Bet

This is actually really impressive. Stu Unger, one of the best blackjack players of all time, had a prodigious mathematical mind and memory. Another high-roller Bob Stupak challenged him to memorize three decks of cards in a row for $100,000. Knowing Unger’s abilities, it was considered a fair bet. Unger watched the cards be dealt and then returned to the shoe. He then recounted all 156 cards without missing a single one. Stupak paid him with, assumedly, a dumbfounded look on his face.

#1: The Archie Karas “Rollercoaster” Bet

Legendary gambler Archie Karas has the wildest bets anyone can think of, but his one probably is one of his wildest due to the extremity of the winnings…and losses. Karas showed up in Vegas with $50 in his wallet and began playing. In the course of three years, he turned that $50 into $17 million, going into the Las Vegas record books as the most ridiculous winning streak of all time. After being banned from the poker tables he began doing $100,000 bets on single dice rolls. The end of the ride brought him straight back down to ground level, losing everything he had won in just one short year.

Out of all the craziest bets out there, these have got to be the top 5 craziest. This in a few years will definitely change, though. Gamblers keep coming up with the strangest things to bet on. It is just a matter time until someone else knocks the pants off of these.


Simon is an overactive gambler and the Staff Writer here at Silver Oak. He loves casino bonuses, online slots, and using the em dash too often. Currently, he rests his typing hands in Vancouver, Canada.