7 Biggest Poker Wins of All Time

Poker has undoubtedly seen significant growth again in recent years, both online and in a live setting. Tournament series like the World Series of Poker, World Poker Tour, and 888pokerLive are seeing continued growth in the number of entries at events around the world.

Players are now regularly battling it out for millions of dollars on the line. But what also makes poker great is that Regular Joes can sit and play among the greatest players in the game – and sometimes come out on top. With so many events and big poker stages, the game seems to be in good shape.

So, what are some of the biggest payouts in the game? That’s a difficult question to answer, considering high rollers have become so popular in recent years, Some other more modest buy-in events, paying out big chunks of cash as well. With a healthy mix of nosebleed stakes events as well as more “reasonable” buy-ins (the $10,000 WSOP Main Event at one time was considered high stakes), here’s a look at seven of the biggest wins in poker history.

Biggest Poker Wins Chart:

Biggest Poker Wins

1 – Jaime Gold Conquers the 2006 WSOP Main Event

The 2005 World Series of Poker was right in the height of the poker boom. Chris Moneymaker’s incredible 2003 run in the Main Event, after he qualified online for only $86, inspired many to take up the game. Moneymaker, the newest member of the Poker Hall of Fame in 2019, helped kickstart a poker boom, as his run to the title and a $2.5 million payday played out in front of ESPN cameras.

The debut of the World Poker Tour earlier in the year, as well as the growth of online poker, also helped grow the game’s popularity. The WPT became the first to show players’ hole cards and was an instant hit.

It was into these poker shockwaves that Jamie Gold entered the Main Event in 2006. The event had seen massive growth since Moneymaker’s win, which featured 839 players. That ballooned to 2,576 in 2004 and then a gigantic 5,769 a year later. Gold faced a field that would become the biggest in history with 8,773 ponying up a year’s worth of house payments for some.

Gold brought some pretty unorthodox strategy and unique “speech play” to the table. He frequently exposed some of his cards and seemingly talking opponents into folding better hands. A talent agent and TV producer from the Los Angeles area, Gold could apparently do nothing wrong. It was mostly positive when Gold finally took the title for a record $12 million. His father’s absence from the final table due to Lou Gehrig’s Disease was a disappointment to the new champ.

“It was unbelievable, and I just remember thinking that there was such a commotion going on,” Gold later told ESPN. “The fact that my father couldn’t be there is just so upsetting to me.”

It was a massive win for a player who isn’t a full-time player – the biggest field and most significant cash in Main Event history. One interesting postscript to Gold’s victory was that he was sued by a former backer and reached a financial agreement in 2007.

  Nationality – This entertainment producer and talent agent is originally from Kansas City, Missouri, and moved to California as a child.

  Huge field – He topped the biggest field in WSOP history.

2 – Antonio Esfandiari Wins the One Drop

A million bucks is a lot of money and playing poker for that amount seemed unique and unheard of in 2012. The WSOP’s Big One for One Drop would indeed require putting up $1 million in the tournament. It featured a massive buy-in, the largest at the time, with anenormous chunk of the prize pool ($111,111 from each buy-in) going to charity.

The One Drop Foundation provides fresh-water services to third world countries, and the event attracted an interesting mix of poker pros and businesspeople. They included Daniel Negreanu, Phil Hellmuth, Sam Trickett, Antonio Esfandiari, Brian Rast, MGM executive and 1978 WSOP Main Event winner Bobby Baldwin, Cirque du Soleil founder Guy Laliberte, and numerous others.

The number of entries was capped at 48 and produced a prize pool of almost $43 million. The event was broadcast by ESPN and only added to the buzz around Las Vegas when it came to poker at the time.

In the end, long-time poker pro and former magician Antonio Esfandiari would top Englishman Sam Trickett for the title and $18.3 million. The win would catapult Esfandiari to one of the most successful poker players in history. It was a highlight for an illustrious poker resumé, his second of three WSOP bracelets in a career that also includes two WPT titles.

“I just can’t believe it,” after his big win. “I’m just so humbled and honoured and happy.

“It makes me feel really good to know that people were rooting for me. I really want to represent the sport of poker for everybody, not just myself. And if there’s any way I can be an ambassador for the game I’d love to be that guy.”

Immediately after his win, it was pandemonium at the Rio as Esfandiari’s friends lifted him in the air in celebration of the biggest win in poker history. A jack of all trades, Esfandiari would indeed go on to be an ambassador of the game and has become part of ESPN broadcasts in the commentary booth in recent years. He remains one of the most popular and most prominent names in poker.

    Nationality – While he was born in Iran, Esfandiari spent the great majority of his life growing up in San Jose, California.

  Huge buy-in – This Big One for One Drop was a huge event at the time and broadcast by ESPN.

   Prestige – Esfandiari received a massive diamond-encrusted WSOP bracelet for his efforts.

3 – Elton Tsang Takes High Roller in Monaco

In 2016, the WSOP held another massive high roller – this time in Monaco. The €1 million Big One for Drop this time featured an international field of 28 players with a prize pool of more than $27 million. The tournament was part of the WSOP’s One Drop Extravaganza Monaco, which also featured four other high roller tournaments to help raise money for the charity.

After three days of play, Elton Tsang came out on top. A regular in high-stakes cash games in Asia, Tsang lives in Hong Kong where he also runs several businesses. He is credited with organising the first major poker tournament in Macau, which eventually became the Asia-Pacific Poker Tour. He’s even played in the “Big Game” in Las Vegas at some of the highest stakes in the world with players like Doyle Brunson, Patrik Antonius, Gus Hansen, Phil Ivey, Tom Dwan, and others.

Winning in Monaco was a massive bullet point for Tsang’s career. He took home $12.2 million for his efforts and a specially designed WSOP bracelet. Russia’s Anatoly Gurtovy won $6 million as runner-up. American Rick Saloman finished third for $3.3 million. After the event, Tsang said the cards just seemed to go his way.

“I was pretty confident,” he told WSOP.com. “But you still need cards to hit in tournaments. I was feeling good, feeling comfortable, getting cards. My bluffs were working, [I was] getting a good read on the table. It was just going my way.”

Along with massive buy-in tournament events, Tsang has also been involved with some huge cash games pots.

The one below happened at the Triton Super High Roller Series in 2018, which produced a pot of more than $1.5 million.

   Nationality – Tsang was born and raised in Vancouver, British, Columbia, Canada, but now spends much of his time playing poker and businesses in Asia.

4 – David Chiu Scores Biggest WPT Payout in History

It may not have been a $1 million buy-in, but $25,000 in the 2008 WPT Championship at the Bellagio in Las Vegas was pretty steep. The WPT was in its sixth season, and televised and online poker continued to fuel the poker boom.

Seven-figure scores were nothing new to the WPT, and the tour produced 11 seven-figure champions out of 18 events in Season VI alone. The finale featured the most significant buy-in of the season for the chance at the title in the WPT Championship. The buy-in was massive at the time, even topping the $15,000 of the Bellagio’s Doyle Brunson Classic Championship (later the Five Diamond World Poker Classic).

While he may not have been a poker legend like Brunson, Chiu had been around poker for years. That included four WSOP bracelets by the time he was playing WPT events. The win at the Bellagio didn’t come easy, and Chiu had to overcome a 6 to 1 chip deficit to poker legend Gus Hansen.

Chiu topped a field of 545 for almost $3.4 million, which became the WPT record for the biggest payout in tour history. He had played only two hands before finding himself heads-up with the Great Dane.

“In a poker tournament you really don’t have to knock everyone out to win,” he told WPT.comin understated fashion after his victory. “He’s a super good player, and he got the chip lead, but I was taking my time and doing what I was supposed to – waiting for my hands. Soon I started catching some hands and got lucky.”

Hansen had eliminated every other player at the final table except Chiu. His tenacity heads-up denied his opponent a much-coveted fourth WPT title. Chiu’s record win still is the biggest in WPT history.

   Nationality – Originally from Davenport, Iowa, Chiu now calls Las Vegas home.

5 – Hossein Ensan Conquers Gigantic 2019 WSOP Main Event

After some ebbs and flows in the WSOP Main Event field sizes following the poker boom, the tournament has begun to grow again over the last five years. That was highlighted by the 2019 event, which became the second-largest Main Event with 8,569 players and a prize pool of almost $81 million.

After ten days of play, 55-year-old Hossein Ensan came out on top, taking home $10 million and a huge winner’s gold bracelet. Originally from Iran (the third Main Event winner from the country), Ensan has lived in Germany for several years, and this marked his first Main Event entry. It was quite an accomplishment for his first time in the tournament.

“I am so happy,” he told WSOP.com. “I thank my fans at home in Germany, also in Iran and my fans, my buddies here. This is the best feeling in my life. Unbelievable! I am so happy. I’m here with the bracelet in hand. What can I say?”

Ensan brought a big chip lead into the final table and then engaged ina marathon heads-up battle against Italian pro, Dario Sammartino. At age 55, Ensan became the oldest Main Event winner in 20 years. Noel Furlong won the title in 1999 at age 62, and Ensan broke a long streak of twenty-somethings winning the title.

Before this win, Ensan had $2.7 million in career live tournament earnings including several nice wins in European events.

He’s now considered poker’s world champion for the next year.

   Nationalty – Ensan has lived in Germany since age 25 and has been a regular in European tournaments for several years.

  Huge field – Fourteen years after a Main Event record for entries with 8,773, poker is again on an upswing, and the 2019 event featured 8,569. Will a new record be set in 2020?

   Prestige – Another gigantic bracelet for a gigantic win. Many may not know, but the Main Event bracelets awarded over the last few years features a latch that opens up to a compartment to hold the player’s final winning cards. Ensan’s last two cards were K♥ K♣.

6 – Brian Rast Bags Super High Roller Bowl Championship

The Super High Roller Bowl (SHRB) has grown in popularity since it debuted in 2015. That inaugural event featured 43 players plonking down a massive $500,000 buy-in - with some of the biggest names in poker getting in on the action.

A roster of those playing is a who’s who of some of the best minds in the game. Eventually emerging as the winner, after three days of play, was long-time pro, Brian Rast. He took home $7.5 million and the coveted championship ring. It was quite a win for Rast, who battled heads-up against experienced poker pro, Scott Seiver to take down the tournament.

“It was an amazing tournament; what a roller coaster ride at the end,” he told CardPlayer magazine after his win. We were playing for a lot of money there at the end, and it’s amazing to be able to run good and win.”

Rast, originally from California and now living in Las Vegas, has $21.6 million in live tournament winnings and is no stranger to high roller events. That includes winning several Aria High Roller events in Las Vegas with payouts in the high six figures. He also won the $50,000 Poker Players Championship at the WSOP in 2011 for $1.7 million and made it a double in the same event in 2016 for $1.3 million. He now has four WSOP bracelets and is one of the sharpest players in poker.

The Super High Roller Bowl remains a popular event with the buy-in lowered to $300,000 since that first tournament. Many pros enjoy it being rake-free, but registration in 2018 dipped 36.

The event is live-streamed by PokerGO, and the network recently announced that the franchise will be expanding into London, set for Sept. 13-15 with a buy-in of £250,000 and a projected prize pool of £12.25 million. The tournament will be capped at 49 players – and there’s a good chance Rast might be one of them.

   Nationality  – Born in Denver, Colorado, Rast spent much of his young life in Southern California, where he was valedictorian of his high school class. He then     attended Stanford University, where he was a regular in the Stanford Poker Club.

7 – Stanley Choi Collects Massive Score in Macau

One of the earliest massive scores in a high roller came in 2012 at the Macau High Stakes Challenge Super High Roller at the island’s StarWorld Hotel and Casino. The high roller scene wasn’t big yet, but this event was a forerunner of many more to follow.

This tournament featured a HK$2 million buy-in (about $255,000 in U.S. dollars). It was a massive sum, and big buy-in tournaments and cash games would follow in Macau through the years. Players like Phil Ivey and Tom Dwan have made the trip to Asia to play.

Stanley Choi ranks as Hong Kong’s all-time tournament earnings leader with $7.8 million. The Macau High Stakes Challenge was a big chunk of that, and he took home $6.5 million after topping a field of 73 players. Also, among the other eight cashing in the event, were John Juanda, Sam Trickett, and Ivey.

Along with playing poker, Choi has several business interests and remains a player on the high-stakes scene. That includes more Triton Super High Roller events.

Here’s an example Choi playing in some high stakes cash game action.

  Nationality – Choi’s win represents the growing Asia high roller scene, which continues to draw players from around the world for some nosebleed action.

  Prestige – There was actually a pretty big turnout for this event with some pretty big names. Events like the Super High Roller Bowl have drawn fields in the 40s in recent years, and this event almost doubled that.

  Huge buy-in – The buy-in and payout were both massive. They may be dwarfed by some now, but the event remains a forerunner to other high-stakes tournaments around the world.