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Unusual Bets

I've spent half a century writing for radio and print (mostly print). I hope to still be tapping the keys as I take my last breath.

If you have a mind to, you can bet on anything. Sporting events get the lion’s share of wagers, but you can also put money on when the first human will set foot on Mars or who will be the next pope.

If you have a low tolerance for risk, you’d be advised to stay away from betting on horse races. As we’ve seen, even a prestigious race such as the Kentucky Derby, where you’d expect anti-doping vigilance to be at its highest, can be tampered with. Following are some strange bets.

The Man in the Bottle

John Montagu, 2nd Duke of Montagu, was very fond of practical jokes. His mother-in-law, Sarah Churchill, Duchess of Marlborough, said of him that he liked “to get people into his garden and wet them with squirts, and to invite people to his country houses and put things in beds to make them itch, and twenty such pretty fancies as these.”

One of his jokes turned into a bet. In 1749, in the company of fellow aristocrats, Montagu said he could fill a theatre by promising something that was impossible. “You’re on,” said Lord Chesterfield (or whatever the equivalent phrase might have been in Georgian England).

The trap was set. Advertisements appeared in London newspapers announcing that “The Bottle Conjurer” would be appearing at the Haymarket Theatre. Among the astonishing feats of magic, the performer will take “a common wine bottle, which any of the spectators may first examine; this bottle is placed on a table in the middle of the stage, and he (without any equivocation) goes into it in sight of all the spectators and sings in it; during his stay in the bottle any person may handle it, and see plainly that it does not exceed a common tavern bottle.”

On the appointed evening, the theatre was packed to the rafters. Then, an employee announced that the Bottle Conjurer would not appear and everybody would get a refund. The audience was not happy, and they trashed the theatre, but Montagu was happy. He had won his bet that people were gullible enough to fall for his hoax. Cash will be fine, m’lord.

The prankster John Montagu, 2nd Duke of Montagu.

The prankster John Montagu, 2nd Duke of Montagu.

The Breast Bet

Brian Zembic became famous as “the man who would do anything to win a bet.” Live in a friend’s bathroom for a month? He did that and won $7,000. How about sleeping under a bridge for a week with $20,000 tied to his leg? He did that.

Then came the breast bet.

Zembic is described as both a magician and a professional gambler, specializing in blackjack and backgammon. In 1996, he and a couple of fellow gamblers were discussing breast implants, as you do.

The conversation went back and forth and ended up with the placing of a $100,000 bet. The deal was that Zembic was to have silicone breast implants and to keep them in for a year. Not only did Zembic win the bet, but he has kept the implants installed for more than 25 years.

Two Clips of Zembic a Dozen Years Apart

Bets that Went Horribly Wrong

Airline pilot Alexander Kliuyev gambled with the lives of his passengers and lost. In October 1986, he was approaching the airport of Samara in Russia when he made a bet with his co-pilot. Kliuyev boasted he could land the Tupolev Tu-134A without visual aids.

The cockpit curtains were drawn, and the air traffic controller ignored them. The aircraft smacked into the runway at almost full speed, killing 70 of the 94 passengers and crew. Kliuyev survived the crash and was handed a six-year prison sentence.

This confirmed the truth that there are old pilots, and there are bold pilots, but there are no old, bold pilots.

Tupolev Tu-134A .

Tupolev Tu-134A .

The bets themselves are not fatal; it’s losing them that leads to trouble. Researchers at Lund University in Sweden studied 2,000 people with gambling addictions. Over a period of 11 years, they found the study group had a suicide rate that was 15 times higher than the general population.

Back in Russia, Andrei Karpov was playing poker; not very well, it seems. He ran out of chips and would have had to leave the table, except he put his wife in as a bet. He lost the hand and the lovely Tatiana. Quite understandably, she objected to being no more than a poker chip to her husband; divorce followed.

But there’s an ending that is happy-ish. Tatiana started dating the man who won her in the bet, Sergey Brodov. Soon, she became Tatiana Brodov.

Super Bowl Bets

The American Gaming Association says $325 million was bet legally on the 2019 Super Bowl, but this is dwarfed by non-regulated bets estimated to have been $5.7 billion. Gamblers can simply wager which team will win, but there are many with a taste for a more exotic flutter.

Here are some of the weird bets available for those who like to colour outside the lines; punters have been able to bet on:

  • Whether the national anthem will last more or less than two minutes;
  • Will dogs appear in Super Bowl commercials?
  • Which player will dump a bucket of Gatorade on the winning coach?
  • Will a fan run onto the pitch?
  • How many commercials will appear during the game?

Let’s end with a nice, romantic football story. John Grant (Chicago Bears fan) and his wife Nicole (Green Bay Packers fan) were watching a game between the two teams in a bar. So we suspect that wobbly pop was a factor. A bet was struck; if the Bears win, John would taser his wife and vice versa. The Bears won 27-20, and the couple went outside for a smoke. That’s when John Grant tasered Nicole three times.

Police were called, and Grant was charged with illegal possession of an electronic weapon; he got a $250 fine.

Bonus Factoids

  • There are bookmakers who will take your money and give you odds of the end of the world happening. So, if Armageddon arrives, how will the bettor collect their winnings? They probably haven’t thought this through completely, although the bookie surely has.
  • Ashley Revel, 32, sold everything he owned, including most of his clothes, in March 2011. He went to Las Vegas and put $135,000 on red at the roulette table; the ball dropped on red seven, and Revel walked away with $270,000.
  • Theodor Geisel, better known as Dr. Seuss, won a bet with his publisher, Bennett Cerf, co-founder of Random House. Cerf wagered that Geisel could not write a book using just 50 words. The result was Green Eggs and Ham, and Geisel won the bet.


  • “13 Bizarre Things You Can (Legally) Bet On.” Lauren Cahn, Reader’s Digest, March 13, 2020.
  • “12 of the Craziest Bets Ever Made.” Liz Sinclair,, January 23, 2019
  • “13 Weird Historical Facts.” Eugene Byrne, BBC History Extra, June 27, 2018.
  • “Problem Gamblers at 15 Times Higher Risk of Suicide, Study Finds.” Rob Davies, The Guardian, March 13, 2019.
  • “I’ll See Your Bet and Raise You … My Wife.” Dwight Perry, Seattle Times, February 1, 2007.
  • “From the National Anthem to Puppies in Commercials, Here Are 17 Strange Prop Bets for Super Bowl LV.” Tyler Lauletta, Insider, February 3, 2021.

© 2021 Rupert Taylor


Miebakagh Fiberesima from Port Harcourt, Rivers State, NIGERIA. on May 21, 2021:

I'm not a better yet. But the Power Ball with its three figure million dollars fascinated me. Kind of me thinking to figure how to keep some money aside for the game.

John Hansen from Australia (Gondwana Land) on May 20, 2021:

All very interesting, Rupert. People will bet on anything and bookmakers and others exploit that fact. The trouble is having bets on everything like how many points a team will win buy, first scorer, most touchdowns etc etc...leads to players getting death threats if they don’t perform etc. Fantasy Football leagues are causing the same thing as well.

I used to be a betting racing only. Well I still do, but very rarely, like the Melbourne Cup. I browse the fields now and then just for a name that is relevant or maybe race six number six barrier six, as that is my birthdate and favourite number. Invariably they come sixth lol. No actually I usually invest $10 at the start of the year. If I lose that I’m done and bet no more for the year. This year I have slowly built it up to $100. Instead of an addiction it is now just a part-time hobby.

Rupert Taylor (author) from Waterloo, Ontario, Canada on May 20, 2021:

Some people just shouldn't parents. I remember the story of a man who went on school trips dressed in women's clothing. His poor kids must have suffered terribly.

Okay, if that floats your boat, but not if it opens your children up to bullying and ridicule.

Rupert Taylor (author) from Waterloo, Ontario, Canada on May 20, 2021:

Brenda you are quite right that there are "All kinds of ways to bet in this world," and it seems a large number of them end in tears.

Rupert Taylor (author) from Waterloo, Ontario, Canada on May 20, 2021:

Miebakagh Ashley Revel's bet puts the lie to the well-known advice that If you want to make a small fortune at a casino start with a large fortune.

Miebakagh Fiberesima from Port Harcourt, Rivers State, NIGERIA. on May 20, 2021:

The Ashley Revel bet with one and win double is an odd. Otherwise, many or frequent wins could be common. Your article is an interesting read. Much thanks.

BRENDA ARLEDGE from Washington Court House on May 20, 2021:

This article is full of amazing information.

It's hard to believe some of the things people bet on.

Like Dr Suess book written from a bet of 50 words. Wow.

The airplane...well that one was sad. Taking people's lives over a bet is awful.

The man boob thing has to be embarrassing to his little gal. How do you explain an eccentric dad like that to your friends.

The ending...getting tassed after losing a bet and armageddon....I don't think that's been thought through.

All kinds of ways to bet in this world.

Shauna L Bowling from Central Florida on May 20, 2021:

Yeah, I came back and watched the video at lunchtime. I wondered the same thing about who pay him annually. I feel bad for his daughter. I would be embarrassed if my dad did something like that just for money!

Rupert Taylor (author) from Waterloo, Ontario, Canada on May 20, 2021:

Hi Shauna. Apparently Zembic gets $10,000 for each year he continues to sport his fake breasts. However, it's unclear who keeps paying the money; somebody with a penchant for creepiness perhaps.

Shauna L Bowling from Central Florida on May 20, 2021:

I'm not a better, but this was quite interesting. What's really cool is "Green Eggs and Ham" is probably the most famous of all the Seuss books.

Is there a reason Brian Zembic has sported his implants for more than 25 years? Is there a bet attached to that, or does he simply like having boobs?