Andrew Barber @ abarber1

I'm too busy right now, but ultimately I really want to make a list of the best bets of all time. Write or post links to your choices ... Bonus points for stories not from the world of poker or gambling!

Most of the respondents didn’t fight for bonus points. We’ve collected the most interesting stories and provided some of them with links to the archived materials.

Dan Smith

Ultimate fight between Olivier Busquet and JC Alvarado!

The rivals agreed to the duel in October 2015, and it was held in 2016. JC, who is significantly lighter than Olivier, bet $ 150k against $ 120k.

– It was not my evening, but there will be no excuses, – JC wrote after the fight – Congratulations Olivier, great job. Kicked my ass well.

Busquet disclosed details of the bet, his preparation and the fight itself on Joe Ingram’s podcast. Quoted staying: In the end, this fight seems like the best event of my life.

Johnny Weibes

Do you remember the guy who made breast implants for himself as a bet, and when he received the money, he decided not to do the reverse operation, because he liked the new breasts?

Magician and blackjack and backgammon specialist Brian Zembich, nicknamed "The Magician", was born in 1961. At the end of the 90s, he was considered as someone willing to do anything for the sake of victory. His most famous bet came in 1996, when he agreed to have breast implants and walk around with them for a year to win $ 100,000 ($ 170,000 in 2021 dollars). The story ended exactly as Weibes wrote. We decided not to include photos of the winner for aesthetic reasons.

Wikipedia article

@ jmprice86

In mid-December 2020, I bet 2 to 1 that Joe Biden will become President of the United States after his inauguration on January 20, 2021. Does that count?

Andrew Barber

If I ever have grandchildren, I will definitely entertain them with stories of betting on the 2020 elections.

We wrote about the bets made before the elections in this news review , but many poker players accepted bets on Trump after the announcement of the result, from those confident of a forthcoming change to the election results.


Phil Hellmuth's three-point shot without warm-up, which earned him $ 15,000.

Doug Polk, Tonkaaaa and Todd Anderson gave Hellmuth 10 to 1 that Phil wouldn’t be able to score a three-pointer in one try without a warm-up. At two o'clock in the morning, the wagerers found a suitable ring somewhere in Pittsburgh, and it was time for some white magic …


Antonio Esfandiari's commitment to a year without sex. Antonio lost this bet.

Antonio Esfandiari ( from PokerStrategy interview ( ):

– “What happened is we were in Sweden drinking. I was a couple of gin and tonics in, and it came up somehow. My buddy, Bill Perkins, said, "For a million dollars you'd have to go the whole year." I'm someone that values and respects money, and I just said, "I think I could do it for 500K."

All I could think of was another buddy of mine, who's a very spiritual, Yoda, Zen kind of guy, he went two years without any release. He did it, and he said it was one of the greatest learning experiences of his life.

That’s all I was thinking about, and while I'm thinking about this in my head, my friend, Bill, puts his hand out and he goes, "Offer expires in ten seconds." I'm like, "Shit. Half a million bucks, but I can't release for a year?"

But what about if you 'released' in your sleep, (Which is probably what would happen)?

– That wouldn't count. But if I induce release, self or assisted, in any way, shape, or form, I would lose.

Anyway, he's like, "Ten, nine, eight …" and I'm thinking, "Wow. Half a million dollars is a lot of money," but I'm not even thinking about that as much as I'm thinking about the experience of actually doing it, and the accomplishment after the year, and then I could focus and put all my energy towards other things in my life. It takes a lot of energy.

When he got to six seconds, I just put my hand out and shook his hand; and then afterwards, as soon as it was done, I was like, "Wow! Did I really just do that?"

I wasn’t even worried about it. Then the next couple days I spent doing a little bit of research and calling my other friends who I know had done it, and I realised that, as much as I thought I could do it, it was something that I didn’t want to do. As a man, what is my purpose of being here? To put one of those things, one of the most important things, on the shelf for a year was going to be really tough.

It wasn’t that I couldn't do it, but it was because I all of a sudden didn’t want to do. After nine days, I wrote a very heartfelt letter to Bill, and I said, "Look, I'm going to do this bet. There's no part of me that’s going to lose the half a million; but it's something that I don't want to do." I offered a buyout for X amount, and he took it. If he wanted more than that, I probably wouldn't have paid him; but I just paid it, got it out of the way, and broke out of the bet. So yes, it's true, and I did buy out, and I'm happy to have paid the money and be done with it.


No wonder. They say that Esfandiari took another bet: he bet $ 25,000 that he would not eat flour for a whole year, and bought out after an hour and a half.

James Vogl

David Gray and vegetarian Lederer's argument over the $ 10,000 cheeseburger is my favourite story. (Lederer calmly ate the burger and took the money.)

Plus a couple more stories from the chapter of the book about Full Tilt Poker, which I wrote , but apparently not very well – the text was not accepted by the publisher.

... In the summer of 2004, a month after the launch of Full Tilt, Lederer and Huck Seed were at the same table in a charity tournament. The screens were showing Olympic gymnastics competitions (the Olympics were in Athens), and Seed said, "I think I could quickly learn how to do a backflip." Lederer knew that his interlocutor was a great athlete, who was even part of the main team of the California Tech basketball team, but Seed's two-metre height seemed to him a strong counterargument. They agreed on $ 10,000 and 48 hours of preparation.

Lederer didn’t know that Seed's uncle was a circus acrobat. They spent the next two days practising at the edge of the pool, after which Seed (who was also a little tipsy) performed a perfect backflip in front of Lederer. The delighted Lederer paid with a smile.

Lederer has always had a hard time battling his weight. A few years after the somersault, his weight exceeded 300 pounds. Seed, who weighed about 200 pounds, had another problem – he wanted to gain weight. So they joined forces in a joint wager, having agreed on $100,000 with the legendary street backgammon player Mike Svobodny, that in a year their body masses would be equal. It didn't work out. After admitting defeat, Lederer underwent surgery to have a stomach reduction.

During the World Series of Poker, Seed and Lederer had an argument about golf. Seed bet six figures that he would finish the course in less than 100 hits four times a day, playing in the desert and using only a five-iron, sand-wedge and putter. He even let Lederer choose a day.

Lederer waited for the hottest day, and at six in the morning they hit the links. In the first attempt, Seed was one hit over his required average and at 8:30 went out for the second round. It was getting hotter and hotter and in addition, as per the bet conditions, he couldn’t use a car or a caddy, so the distance between the holes had to be covered on foot. The temperature that day reached +47, but Seed methodically improved his score over each next attempt and came out victorious.

Len Ashby

In Bobby's Room, I think Huck bet $ 5k he could jump from the dealer's seat over a table and land next to a glass wall and without touching it. He jumped like a frog, landed like a gymnast, and won. If you go to Bellagio, take a look – it looks absolutely impossible.

Barry Carter

I thought about writing a book about betting, but gave up the idea, because the topic turned out to be much more complicated than I thought. I don’t remember the details, but I found out that most of the stories about Huck Seed's bet aren’t being told that reliably, and a lot of the bets attributed to Amarillo Slim were actually made by Titanic Thompson.


When Joe Ingram played 50 thousand hands in a day.

Joe Ingram:

I had to play 50k hands in 24 hours and still show a plus at the tables. Played NL25, finished in 20 hours, won about 45 buy-ins plus $ 30k for the bet. I was streaming all the action on long before poker streaming became fashionable. If Twitch had been around earlier, I’d have become a top streamer with insane sessions and action. In those days, I was a completely insane grinder.

Over 20 hours of play I ate practically nothing, but I decided it’d be GTO to stock up the table with fast food.


It was like Ashman's completely wild marathon bet. Hasib also participated in that.

Andrew Barber

Classic. 70 miles in 24 hours.

You can refresh your memory of this bet with our longread translation on Hasib Qureshi , who lost $ 300,000 to his friend. At the time, the odds on Ashton Griffin, who had never run a marathon, to win were estimated at 0-5%.

Nate Mavis

The first ocean-to-ocean road race across the United States was the result of a bet.

From the Wikipedia article on Horatio Nelson Jackson:

... At the beginning of the twentieth century, it was believed that the fashion for cars would quickly fade away, and in general they were just entertainment. As a guest of the University of San Francisco, on May 18, 1903, Jackson wagered for $ 50 (in 2020 dollars – $ 1,440) that he could cross the country in a four-wheeled car. He was then 31 years old, he didn’t have his own car, or any driving experience, and there were no road Atlases. Jackson was visiting California with his wife and they were due to return to Burlington, Vermont. So his wife went home by train while Jackson stayed to learn to drive and prepare for the trip.

He teamed up with a young mechanic and chauffeur named Sewell Crocker. Crocker advised Jackson to buy a Winton Motor car. He bought a used two-cylinder car, which he named "Vermont". On May 23, he left San Francisco, taking a coat, rubberized protective suits, sleeping bags, sheets, a camp kitchen, a water wineskin, an axe, a shovel, a telescope, a set of tools, spare parts, a winch, cans of gasoline and oil, a Kodak camera, a rifle, a shotgun and some pistols.

Jackson took into account the unsuccessful experience of Alexander Winton (the designer of the car of the same name and motoring pioneer), who was unable to cross the desert between Nevada and Utah, and planned a route through the northern states by the Oregon Trail.

After 15 miles (24 km), he punctured a tire. Jackson and Crocker replaced it with their only spare tire – there was no suitable replacement spare in all of San Francisco ...

... On July 26, 63 days, 12 hours and 30 minutes after the start of the race, Jackson and Crocker arrived in New York, successfully driving across North America for the first time in history. During the trip, they burned 800 US gallons (3,000 litres) of gasoline.

In New York, Jackson met his wife, and in the same car they drove home to Vermont. 15 miles before home, the car broke down again. His brothers came to the rescue in their two cars. Jackson's car was repaired, but when everyone started off, both brothers' cars broke down simultaneously, and Jackson had to tow them all the way home. Literally at his garage door, his drive chain burst – one of the few parts that had never had to be changed during the entire trip ...

Who would believe that a car like this could cross an entire continent?


Some dude got 5 to 1 for 100k that he could eat $ 1,000 worth of McDonald's in a day and a half. Failed in the most pitiful way. Obviously doomed from the start.

Little-known regular Mike Noori made this bet against famed tournament director Matt Savage. He was allowed to drink liquids, but the cost of drinks were not included in the bill. He was permitted to get rid of food by the old two-fingers-in-the-mouth method only once; and no medication was allowed. And salad could account for no more than $ 200 worth of the bill.

The rest of the details can be found in the topic for 2 + 2 ( .

On the day of the bet, ill-prepared Noori ate only $ 95 before throwing in the towel.

Hot dog prop bet

Another famous bet, described on 2 + 2, ( took place under this slogan .

MTT regular Jim "Foundinflood" bet $ 1,000 against Colin's $ 1,500 "Silent_0ne" (both active posters on the 2 + 2 forum), claiming he could eat 450 hot dogs in April – 15 a day.

Basic rules:

– From midnight on April 1 to 23:59 on April 30, you need to eat 450 hot dogs;

– The food process must be recorded on the webcam;

– Ketchup and other additives – optional;

– Vomiting is acceptable, but not regular – no more than four times in the entire month.

Energy values: sausage – 120 kcal, 18% saturated fat; 15 sausages have 1,800 calories and 270% DV for fat;

Rolls – 110 kcal, 1,650 kcal per day;

Total calorie content – 3,450 kcal per day.

The average daily intake for an adult is 2,000 kcal.

He seems to be on the left in the photo – the same Jim

The 2 + 2 thread has grown to over 80 pages. After a bitter struggle, Jim won. Only got sick as a result once and only after the very last hot dog.

Neil Channing

Roland [de Wolfe] bet Phil Ivy that he wouldn't get a haircut that year. A very deeply thought out bet, in my opinion.

After about a month or two, Ivy realised that with such hair he would look absolutely obscene, and he’d have to stay at home all year (before it became mainstream). After that, he paid off.

Alex Hwang

Ivy made a million dollar bet to give up meat and bought out of that too, do you remember how long he lasted?


About a week.

Joseph Graber

A bet between Perkins and the Staples brothers, weight loss for one and gain for the other.

And we wrote about this in the news review in 2017.

Bill Perkins, who has gathered famous poker streamers on his yacht, made an original bet.

Brothers Matt and Jamie Staples must reduce the weight between them to one pound (0.45 kg) in a year. Jamie weighs 141 kg, Matt weighs 61 kg. The Staples bet $ 3k against Bill's $ 150k.

At the beginning of the journey, Jamie weighed 138 kg, and Matt weighed 61 kg. In the end, they met at around 85 kg.

Rauf Malek

Between Matusow and Forrest, of course!

On May 5, 2010, Phil Hellmuth tweeted that Forrest and Matusow had entered into an agreement that would require Forrest to slim down from 188 lb (86 kg) to 139 lb (62.5 kg). If Ted managed to fulfil the condition before July 15, he’d receive two million dollars, if he metthe conditions before September 24, he’d have had to be content with a million. Otherwise Matusov would have received ... $ 150,000.

These fantastic odds excited the poker community. Most were of the opinion that Forrest would easily meet the deadline by September, so he was almost guaranteed a million. Hotheads offered Ted to amputate both legs, calling it the easiest way to make two million dollars. But Ted got by with proven means. “The last two months passed under the motto ‘Run, Forrest, run!’”

Shortly after the start of the main event of the World Series, Mike Matusow wrote on his Facebook page: “Wonderful day: Ted Forrest already weighs 142.6 pounds and has three more days left. Should lose weight without problems. According to him, he hasn’t eaten for 9 days. "

On July 13, the bet ended. Mike Matusow: “Ted Forrest weighs 138 pounds. He looks like he's been receiving radiation therapy; I hope his health is all right. "

The victory, however, turned out to be pyrrhic. Matusow didn’t have two million to pay as promised, but everyone knew about it when making a bet. The players agreed that Mike would pay off his debt over several years. Ten years have passed, but Forrest didn’t wait for the required amount, and took $ 70,500 from Matusow to spend on restoring his health. We can safely say that both of them lost the bet.

Dan Bilzerian Cycling

In 2016, Dan Bilzerian made a bet with Bill Perkins that he could cover 300 miles (482 km) between Los Angeles and Las Vegas by bike in 48 hours. The conditions looked attractive to Perkins, especially considering that Bilzerian hadn't been on a bike in 18 years.

Having received the consent of his opponent, Bilzerian undertook a solid preparation, on which he spent about $ 100,000, and even hired the famous cyclist Lance Armstrong as a coach for a charitable donation to his charity for $ 25,000. It all turned out quite ridiculously: Bilzerian chose a specially designed bike that he could ride half-lying down, and he made it almost the whole way in the slipstream of the car in front.

It’s believed that Bilzerian won about $ 1,200,000 on this bet.