The Loudest Bets in Poker

Bets in poker are not just entertainment and a way to indulge one's ego, but also a potential source of winnings that can exceed tournament prize money. The 2026 World Series of Poker was no exception, featuring a couple of wagers between the industry's superstars. One of them fell through, while the other did reach its conclusion. And in both cases the central figure was Shaun Deeb.

Shaun Deeb turns down a bet over chicken strips

Right at the start of the WSOP 2026, Shaun Deeb received an offer to wager a hefty sum as part of the $25,000 Fantasy draft. Ben Lamb and Daniel Negreanu put $250,000 on the line. They proposed a fantasy team competition to the now nine-time series champion. Lamb wanted increased odds for his side, since Deeb rated his own chances of winning at 60-65%. However, Shaun refused that condition.

Lamb then proposed a different option: a 1-to-1 bet in exchange for Deeb giving up his beloved chicken strips entirely for the duration of the series. Seven-time WSOP bracelet winner Josh Arieh calculated that this gastronomic passion costs Deeb $83,000 in pure equity. Shaun nevertheless decided not to cut back on fast food and turned down this offer from Lamb as well.

Ben Lamb promised he would keep a weekly tally of Deeb's strips and buy-ins, but stopped doing so after the very first week of the WSOP. At that point the number of buy-ins was slightly higher — 18 against 12. According to projections, Shaun was supposed to eat 75 of them over the whole series. After it finished, the American regular himself revealed that he ultimately stopped at 62 strips with 122 entries. 

Phil Hellmuth bets on his son

Shaun Deeb also showed up in another notable bet this summer. This wager began when Phil Hellmuth revealed that he had offered his son Phillip III the chance to sell pieces of his action in the World Series Main Event at 1.4 markup. That is, 10% of the $10,000 buy-in would have cost a potential investor $1,400 rather than $1,000.

In the comments to Hellmuth's post, Shaun Deeb said the markup was too high given Phillip III's level. The 17-time WSOP champion immediately proposed a bet: he would put up $14,000 that his son would make the money in the Main, and in that case Deeb would have to pay him a sum equal to his son's winnings. And if Phillip III had gone all the way to a bracelet, Shaun would have had to pay $10,000,000. 

Deeb agreed to the terms, but brought crypto investor and former high-stakes professional Jason Mo into the bet, who took on the bulk of the potential costs. In the event that Hellmuth Jr won the Main Event, the nine-time champion was prepared to pay only $1,000,000 out of his own pocket. "I can't afford to risk 10 million. Jason is my rich old friend from Vegas who loves plus-equity spots, so I pulled him into this deal to take most of the risk off myself," Shaun said.

In the end, Phillip Hellmuth III did not reach the money in the WSOP main event, busting alongside his father during day three. However, according to other reports, Hellmuth Sr had bet on the results of both of his sons, putting up $14,000 on each. And Nick Hellmuth went on to finish 1,312th and collect a min-cash of $15,000. In that case Deeb did lose after all, and the 17-time champion came out $1,000 ahead.

Incidentally, Phil Hellmuth later found yet another excuse for a wager. The star regular walked around the casino floor offering other poker players a bet that he could throw an American football so that it stayed on the table. Whether he made any money from it, history does not say. 

Perkins makes Deeb "lean out"

These days Shaun Deeb has no wish to give up his nuggets, but just a couple of years ago he was successfully motivated to switch to a (more) healthy lifestyle. Hedge fund manager and poker regular Bill Perkins managed it thanks to an expensive bet. In March 2023, Deeb put up $100,000 that he would be able to reduce his body fat percentage to 17% by the start of the WSOP in May 2024. Perkins took the bet and promised to pay out $1,000,000 if Shaun won.

At the start of this challenge, Deeb weighed 139 kg with 40.2% body fat. At the same time, the means to achieve the goal were almost unlimited. Under the terms of the bet, Shaun was even allowed to use steroids and hormone replacement therapy. After his first workout, he recorded a message for Perkins: "It's going to be a long 14 months, but I'm coming for you, Bill."

Most of the poker community didn't believe that the two-time WSOP Player of the Year could pull it off, but he surprised the sceptics. Already in January 2024, Dib's body fat percentage dropped to 23.9%, and by the end of February this figure had fallen to 22%. After that, Perkins bought out the bet for $800,000, with three months still remaining before the deadline.

Incidentally, shortly before the bet with Dib, Perkins made a similar wager with Doug Polk. Under its terms, Polk was supposed to shed half of his body fat mass, that is, reduce his body fat percentage from 28% to 13.85%. The challenge started in February 2022 and ended exactly a year later. Polk fell just 1.3% short of victory and lost $200,000 to Perkins.

Perkins vs Esfandiari

Bill Perkins was into various bets as far back as 10 years ago. And the wagers with three-time WSOP champion Antonio Esfandiari stand out in particular. In 2013, the players bet on complete celibacy for a period of one year. As Esfandiari recounted, the bet arose over drinks in Sweden. Perkins offered $1,000,000 for complete abstinence from sex and masturbation, and Antonio said: "I think I could do it for $500,000." Perkins extended his hand and started counting down 10 seconds to make a decision. "When he got to six seconds, I just shook his hand. And right after that, I thought, 'Wow! Did I really just do that?'" Esfandiari recalled.

However, this bet ended just nine days later. According to Esfandiari himself, he thought about the celibacy and realised that he didn't want to do it, despite being confident he could fulfil the condition. He wrote Perkins a sincere letter explaining his position and offering to buy out the bet. Bill agreed, but the two never revealed the buyout amount. Perkins also said that Esfandiari never had a chance of winning, because he was planning to get married in the year of the bet.

In January 2016, at the start of the PokerStars Caribbean Adventure, poker players made another extreme bet. Under its terms, Esfandiari had to move around everywhere and at all times using only lunges for 48 hours. According to several sources, $50,000 was at stake.

Esfandiari spent the first day of the challenge mostly in his hotel room. On the second day, however, he had to take part in the PCA Main Event with a $5300 buy-in. To reach the casino hall, the three-time WSOP champion had to cover about 90 metres along the corridor of the Atlantis resort, performing roughly 300 lunges. At least, that's how Perkins told the story.

During the tournament, Esfandiari needed to use the restroom, but he decided that the pain of going there and back would be unbearable. To avoid this, he relieved himself into a bottle right under the table, covering himself with towels. The tournament director, upon learning of this, disqualified Esfandiari for a gross breach of etiquette. At that point, the American high roller had an average stack.

After the disqualification, Esfandiari continued to follow the terms of the bet and made his way to his room using lunges. The challenge was completed, and he earned $50,000. The WSOP champion soon apologised for his behaviour at the table: "It's kind of sad for me to write this. Everything you've heard is true. I can sit here and try to explain and justify it, but at the end of the day my actions were completely unacceptable. I became a father, and this isn't the example I want to set for my son. On paper I won, but in life, I lost."

In addition, Esfandiari donated the entire winnings from this bet to charity. $25,000 went to the One Drop foundation, which provides drinking water to poor countries, and another $25,000 went to Raising for Effective Giving, a charitable organisation whose members include many poker professionals.

durrrr Challenge

Tom "durrrr" Dwan is the hero of two legendary bets directly tied to play at the table. In 2009, he challenged anyone willing, offering to play 50,000 hands heads-up with $200/$400 blinds in hold'em or Omaha. If his opponent ended up in profit by the end of the match, they would receive $1,500,000 on top of their winnings. If Dwan won instead, the loser would be obliged to pay him $500,000. 

Patrik Antonius was the first to accept the challenge. The rivals met in a PLO match on Full Tilt Poker. The Finnish high-stakes pro started brilliantly, and by the 13,000-hand mark he was up nearly $500,000. But then Tom Dwan turned the tide of the game and kept building his advantage more and more. By spring 2010, the American was up $2,059,000. After 39,436 hands played, Antonius conceded and bought out his bet for an undisclosed amount. The Finn later admitted that he lost because he had never before played heads-up on four tables at once and couldn't adapt to Dwan's style.

durrrr's second opponent was Dan "Jungleman" Cates. Here the story played out the opposite way. Dwan pulled ahead at the start but quickly lost his edge. Then Cates dominated and, over 19,000 hands, pulled ahead by $1.2 million. The game was interrupted by "Black Friday" in April 2011. 

In 2013, Full Tilt Poker resumed operations, and the rivals returned to the table. This time, however, they only played a few sessions. Dwan started preferring matches against other opponents, which irritated Cates. Then Tom stopped responding to Jungleman's messages and never paid him the $1,500,000 he owed for losing the bet. 

The unfinished challenge became a source of hostility between the poker players. Cates has said that Dwan paid him around $700,000 in penalty fees. The two only reconciled in 2025, discussing the situation in a GTO Wizard video. 

A bet on a World Series bracelet

Bets on winning the World Series haven't always been as widespread as in recent years. Their rise in popularity was driven by a dispute Eli Elezra had with a whole group of high-stakes pros in 2007. It arose from a conversation between Elezra, Doyle Brunson, Phil Ivey and Chip Reese shortly before the start of the WSOP. 

During a cash game, the players discussed whether it had become harder to win a bracelet after the poker boom of 2003. Most participants agreed that the title was still fairly easy to win. Elezra took the opposite position, pointing to the larger fields and the availability of poker literature and strategy.

As a result, Barry Greenstein offered Elezra a bet on his own WSOP win at odds of 10 to 1. Elezra agreed and staked $25,000 against Greenstein's $250,000. Other pros wanted in too, and soon the Israeli player had made similar bets with a number of top players.

Elezra won the bracelet in Event #24 of the 2007 WSOP — the $3000 Seven Card Stud Hi-Lo. The tournament drew 236 entries, and in the heads-up match the Israeli beat Scotty Nguyen, who was chasing his fifth WSOP title, in two hours. Eli Elezra earned $198,984 for first place, but winning the bets brought him far more. In total, across all the wagers, he won more than $700,000.

Elezra's story popularised bracelet bets and encouraged pros to return to smaller buy-in tournaments. Similar bets were made by Phil Ivey and Tom Dwan, who in 2010 nearly landed a huge score on them.

Ahead of the WSOP, bets against Dwan were placed by Phil Ivey (around $1 million), Eli Elezra ($250,000), Mike Matusow ($30,000), Daniel Negreanu, Howard Lederer and other pros. Most of the bets were made at odds of 3.25 to 1, and had he won, Dwan would have earned between $9 and $12 million. 

Tom Dwan reached the final table as chip leader in the $1500 No-Limit Hold'em event, which drew 2563 entries. The final table, watched by hundreds of fans, lasted nine hours, and in the heads-up match durrrr faced New Zealander Simon Watt. Dwan lost a big pot due to an unsuccessful bluff, and by the deciding hand his stack was five times smaller than his opponent's.

Dwan went all-in with Q♦️6♣️, and Watt called with 9♦️9♣️. On the 8♣️A♣️A♠️ flop, the New Zealander made two pair, and on the A♦️ turn he improved to a full house. Dwan needed a queen or an ace on the river, but the K♥️ hit instead. Watt became champion, earning $614,000. 

It was reported that after the heads-up ended, Mike Matusow personally approached Watt and said: «Thanks for saving all of us millions of dollars! What's it like being the hero of every high-stakes player?». Tom Dwan, meanwhile, received $381,885, which at the time was his best cash within the WSOP. However, the American still hasn't won a bracelet. 

Bracelet bets — is it over?

However, it seems that the days of betting on victory in a World Series event are behind us. Under the new WSOP rules adopted this year, third-party payouts for players' results may be deemed to violate the regulations and interests of the series. True, this mostly concerns dishonest attempts to secure such dividends, as was the case with Jesse Yaginuma, who received a bonus from WPT Club World in 2025. Still, by making such bets, poker players risk facing disqualification and forfeiture of their winnings.

But even if the WSOP does ban bracelet bets, high-rolling professionals will always find other reasons for high-stakes wagers. Which means we'll no doubt see players taking on fitness challenges and proving their strength at the poker table again and again, to silence the sceptics and earn some good money.