Biggest Poker Tournament Wins Ever

• Winner: Bryn Kenney* (2nd) 
• Entrants: 54

The 2019 Triton Super High Roller series has the highest single tournament cash to date, coming in at a whopping $20 million. There were 54 total entrants in the tournament, with a £1.05 million buy-in. Although Bryn Kenney finished the tournament in second place, he took home the biggest cash prize because of a deal struck with Aaron Zang. Kenney had about four times as many chips as Zang when they entered heads-up at the final table. They agreed to split the 1st place prize, but seeing that Kenney had more chips, he took home a larger share. Bryn Kenney currently sits second on the all-time money list. 

• Winner: Antonio Esfandiari
• Entrants: 48

For seven years before the 2019 Triton Super High Roller Series, poker legend Antonio Esfandiari held the record for highest single tournament win. The Big One for One Drop event was added to the World Series of Poker in 2012, with $100,000 of each buy-in going towards charity. The first rendition of the event is still the biggest to date, with a total prize pool of over $42 million. Antonio Esfandiari hasn’t been as active in the poker scene recently and sits 20th on the all-time money list, but he still remains one of the greatest and most influential figures the game of poker has ever seen. 

• Winner: Aaron Zang
• Entrants: 54

Although Aaron Zang may have won the 2019 Triton Super High Roller Series, he took home the second largest prize due to an earlier agreement to split the prize money. Zang continually chipped away at Kenney's stack until finally taking a chip-lead after forcing a fold. On the last hand of the tournament, Zang had a middle pair of 8’s to the flop and Kenny had an Ace high flush draw. The river was a dud and Aaron Zang took home the trophy. 

• Winner: Daniel Colman
• Entrants: 42

The third ever WSOP Big One for One Drop featured the fourth largest payout in poker tournament history. It was no easy feat to take down this tournament, as Colman had to take down hall of fame poker legend Daniel Negraneu. On the final hand Colman had KQo while Negraneu had A4o. The flop was jack, ace, four, giving Negraneu two pair and Colman a gut-shot straight draw. It proved to be Colman’s lucky day, as he caught the ten on the river to complete his straight and take home the more than $15 million prize. Daniel Negraneu took home a modest $8 million for second place. 

• Winner: Elton Tsang
• Entrants: 28 (2 rebuys)

The 2016 One Drop Extravaganza in Monte-Carlo is home to the fifth largest single tournament cash in poker history. Interestingly, this is the only tournament on this list with multiple rebuys allowed. Elton Tsang has been a trailblazer in the international professional poker scene, helping bring high-stakes poker across the globe. He founded the first live poker tournament in China and was a part of the biggest pot on live T.V. Elton Tsang most recently won the $50,000 No Limit Hold'em Super High Roller Series in Europe for $684,000.

• Winner: Jamie Gold
• Entrants: 8,773

There is no bigger accomplishment a professional poker player can obtain other than winning a WSOP Main Event bracelet. The yearly poker tournament that has been held in Las Vegas since 1970 is the largest poker tournament in the world. 2006 proved to be the peak of the early 2000’s poker boom, with a record 8,773 entrants competing for the 1st place prize, an increase of more than 3,000 entrants from the previous year. Jamie Gold's 2006 run was one of the most epic and defining moments of the 2000s poker boom. One of the most memorable moments was seeing Gold embrace with his mentor and former WSOP champion Johnny Chan. I highly recommend the above video with Jamie Gold's most memorable hands from the 2006 main event, it truly is one of the best pieces of poker content.

• Winner: Espen Jørstad
• Entrants: 8,663

If there is any sign that the game of poker is in great health, just look at this year's WSOP. The 2022 Main Event brought in the second most entrants to the tournament ever and marked only the third time there were over 8,000 entrants in the main event. Espen Jørstad finished the main event in 6th during the 2021 WSOP Online tournament, and came back with a vengeance in 2022. He was dominant throughout the tournament and looked calm, cool, and collected through every stage. I would keep an eye on Espen Jørstad, because he can easily climb the ranks as one of the greatest poker players to ever sit down at a card table.