People throw the word “bet” around pretty lightly these days. Your buddy bets you won’t tell your wife about that special weekend in Vegas, your brother-in-law makes some insane wager on the Cowboys, you bet all the kids will move out of the house at 18—but what happens when someone takes those insane bets seriously? Sometimes the bettor gets off easy and has to move to the Midwest and at other times, there are man boobs involved.

A Boob for His Bets

This is easily the most insane bet in the entire world, and it proves that there are some men you should never challenge. Brian Zembic is a professional gambler, and evidently takes that title very seriously. Back in 1996, his buddies decided to expand his repertoire from simple backgammon and blackjack. They bet him $100,000 that he wouldn’t get breast implants—whopping 38Cs, no less—for a year.

Well, he did it. Not only did he get them, but he still has them. In addition to earning one hundred grand, his man boobs are allegedly a hit with the ladies as well. Would you ever have plastic surgery for that much money?

Dying to Win the Cash

You’ve probably heard about Matthew Webb. He has the distinction of being the first fellow to successfully take on the English Channel, which he swam in 1875. You might say he was a good swimmer. He certainly thought so, because he literally put his life on the line for $10,000.

The bet? To swim straight across the very turbulent whirlpool located below the equally turbulent Niagara Falls. He gladly took on the bet—and died while attempting it. He gave up at the halfway mark and drowned.

Take My Wife, Please

Andrei Karpov did what many men have probably dreamed of doing: he wagered his wife. During a particularly heated card game, he ran out of money and decided that his wife, the lovely Tatiana, would make excellent collateral.

Guys, don’t ever do this. Do not test your wives. You see, Andrei lost to Sergei Brodov. Tatiana got so mad—like you do—that she made good on the wager, left Andrei, and rode off into the sunset with Sergei. Can you blame her?

Everything on Red


Ashley Revell is a legend. He’s practically a hero. The Brit went to Vegas to seek his fortune, after selling off all of his worldly possessions. When he finished getting rid of his stuff and taking all the money out of his bank account, he had $135,000 to bring to Vegas.

Once there, he made a very bold, very risky move. At the roulette table he put everything on red. The wheel spun, the ball bounced, and lo and behold, it landed on red. In one swoop, Revell doubled his stake. Because he’s apparently a great guy as well as a lucky one, he even left the dealer a fat tip before leaving while he was ahead.

Betting Big on Pop Culture

In 1989, the year 2000 seemed like science-fiction. Nevertheless, a bold, bright, and still unknown gentleman from Wales took 30 pounds to a local bookie, where he made several very interesting wagers:

  • At 8 to 1 odds, he bet that Home and Away, a British show, would still be on the air in 2000
  • At 5 to 1 odds, he said that Neighbours, a British soap, would still be on
  • At 5 to 1 odds, he said the same about East Enders
  • At 4 to 1 odds, he wagered that Cliff Richards, a singer, would get knighted
  • And at 3 to 1 odds, he was absolutely certain U2 would still perform together

Come January 2000, the Welshman returned to his book and confirmed that all of those things had indeed come to pass. That day he left nearly 200,000 pounds richer.

The Million Dollar Game

Super Bowl XXIII paired the San Francisco 49ers against the Cincinnati Bengals. For casino king Bob Stupak, it was a very important game. He was well-known for making all kinds of outrageous bets, but in 1989 he topped everything by betting one million dollars on the 49ers.

Can you imagine watching the game with that much money on the line? Of course the 49ers won, 20-16, and Stupak won as well. In fact, not only did he win a million bucks, he also has the distinction of making the largest bet in Las Vegas, ever.

Real Life Rain Man

Remember Bob Stupak, the million-dollar man? He had a friend named Stu Ungar. Stu Ungar was amazing. He’s still a legend among blackjack players due to his ability to calculate the odds and remember every card dealt. Doubting his prodigious talents, perhaps, Stupak bet him $100,000 that he couldn’t remember every card in three decks—dealt all in a row. He got all of them right, with not one miss out of 156.

A High-Stakes Move

John Hennigan loved to bet, and he was good at it. He was a regular high-roller in the gleaming casinos of Las Vegas, a land that he loved without reservation. However, it seems that perhaps his love of high-stakes gambling was even stronger than his love of Vegas.

His friends decided to make a wager, because they believed John couldn’t leave the bright lights of Vegas for six weeks. Moreover, they decided he needed to detox in Des Moines, Iowa, of all places. Since they were willing to put up $100,000 for the bet, Hennigan accepted.

At least he accepted for about two days. Although he could have easily won six figures, he just couldn’t take it out in the Midwest. Honestly, Iowa’s not that bad—certainly not bad enough to make you pay-out ten grand to your buddies, right? So apparently, John Hennigan did love Vegas more than money.

The next time you decide to make some crazy wager, even if it’s just a figure of speech, make sure you’re not hanging around any of these guys. What’s the craziest bet you’ve ever won—or lost?