Do you remember the first bet you made among friends? I’ve made a lot of them: In grade school, I’d bet friends that they couldn’t run to the fence and back in under a minute (the fence was far away). In high school, I’d bet people that they couldn’t eat two packs of salted crackers in under a minute without water (don’t try that at home). And in college my friends and I would bet on all kinds of alcohol-related shenanigans (once again, don’t try this at home).

Some involved money, others didn’t. And though they seemed outrageous at the time, none of them compared to three most outrageous bets in the history of everything. Here they are. And we bet you can’t read them without dropping your jaw.

1997 -> Man gets breast implants

Did you ever see the Drew Carey Show episode where Oswald follows Lewis’s advice and gets breast implants for $10,000? We’re willing to be it was based on a real life bet up in Canada. Brian Zembic of Toronto agreed to get breast implants for a full year. If he kept them, he’d get $100,000. And he did. In fact, he went one step further and kept them even longer, using his new assets to profit even further. For example, he made cash by flashing them in public. And he made $15,000 by living in a men’s washroom for a month. We’re not clear if he was topless at the time.

2005 -> Man bets that he’ll die

What would you to avoid an inheritance tax? Some people would talk to a tax accountant or lawyer. Arthur King-Robinson, on the other hand, decided to talk to a bookie. In an effort to avoid a £3,000 inheritance tax on his estate, the clever British man bet £500 on 6:1 odds that he would kick the bucket by year’s end. At 91 years old, those are fair odds. For some strange reason that defies logic, the bookies at William Hill, a respected British bookmaker, accepted the bet. He ended up losing the £500, but because he managed to live out the year, he managed to avoid the inheritance tax.

2009 -> Shaq tries to enter the White House

Everyone knows that Obama is a huge basketball fan. So you’d think that an NBA legend such as Shaquille O’Neal would be able to hang out with the President of the United States at a moment’s notice. That’s what Shaq assumed, accepting a bet that he’d be able to gain entry to the White House unannounced. Unfortunately, when he approached the gates, he was denied entry. Thankfully, Shaq didn’t lose any money. He did, however, have to do 1,000 pushups for the loss.

Would you take any of these bets?

What do you think? Would you take any of these bets? Do you consider yourself to be the betting type? If you’re just getting your feet wet in the betting world, give Silver Oak Casino a try. While you can’t bet on things like breast implants, you can double down at the Blackjack tables or work that perfect pair in Video Poker into a big win.


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.