Top 10 Greatest Gambling Rivalries: High-Stakes Showdowns and Clashes

As gambling has become popular, many stars have emerged within the community due to their skill, strategy, and ability to play high-stakes games without breaking a sweat. 

Naturally, these poker superstars have often had to face each other in high-stakes showdowns that have captivated the legions of fans and admirers that support them. 

The tension between the two players, the excitement of the wager, and the anticipated outcome combined make for excellent battles that we have come to expect from high-stakes betting. 

Here are the 10 greatest high-stakes showdowns and clashes in the poker world. 

10. Maurice Hawkins vs. Shyam Srinivasan

Our first entry comes to us directly from the infamous 2015 PCA Main Event, where the feud between Maurice Hawkins and Shyam Srinivasan first began. Where Hawkins is known for making bold moves and reading players’ minds, Srinivasan is known for his mathematical approach to poker. 

It all started in that one fateful PCA event where Srinivasan was commenting after winning over a couple of hands. Hawkins fired back, and the entire round turned into a roasting match which Hawkins eventually won. However, that wasn’t to last long as Srinivasan picked up the pace and, by the end of their showdown, won $110,000. 

Their conflict would eventually die down, and a rivalry would begin for quite some time. Hawkins was a veteran of the sport with his flamboyant personality, while Srinivasan was a rising star with a calculated approach to poker. 

9. Phil Hellmuth vs. Daniel Negreanu

Another relatively recent rivalry between the biggest names in modern Poker started in the late 2010s and finally concluded in 2021. People who have been keeping up with PokerGo’s High Stakes Duel will definitely have an idea of what we are talking about. 

Hellmuth was already on a winning streak throughout the match-up and beat Negreanu two times. Not one to back down, Negreanu doubled the stakes for a rematch, and it all came down to a single $200,000 buy-in heads-up No-limit Hold’em match between the two giants.

The final match went on for five and a half hours, and Hellmuth brought down Negreanu with a ten-hand straight to his rival's nine-hand straight. 

Although Negreanu had previously criticized Hellmuth’s poker style and playing abilities, he accepted the loss with grace and even congratulated Hellmuth. For his part, Hellmuth won a clean $350,000 in winnings, officially ending the rivalry between them. 

8. Tom Dwan vs. Phil Ivey

Phil Ivey has been a major Poker star for over a decade, and he has had some of the most long-standing rivalries in poker. Tom Dwan, with his fearless and aggressive style, was one of the prime contenders in high-stakes poker. A confrontation was inevitable, with both of these giants eyeing the same pots. 

One of the first major clashes between the two was the first-ever televised million-dollar cash game on Hustler Casino Live. The atmosphere was tense throughout the match, but by the end, Ivey went all in, and Dwan called. After the dust settled, Dwan won the $1.1 million pot.

Their rivalry would on to influence multiple other tournaments, like their showdown at the APPT Macau tournament, High Stakes Poker on Poker Go, and the PartyPoker Caribbean Poker finals. 

Although Ivey has been regarded as the best Poker player as of late, Dawn’s legendary bluff against him put quite the dent in his shining armor. Their rivalry has never gone too far, but their matches against each other are a spectacle to watch.  

7. Nick "The Greek" Dandalos vs. Johnny Moss

Johnny Moss and Nick Dandalos are high up in the list of poker legends, but they also had an intense showdown that went on for months.

The early Poker scene was dominated by high-stakes rivalries, but the battle that we are about to describe was like no other. 

Picture the Horseshoe Casino run by Benny Binion in 1949, Moss and Dandalos would start a five-month-long heads-up poker marathon right there.

The match would continuously swing between the two giants, and spectators were left without words as they saw insanely big pots being exchanged continuously.

By the end of the five months, Dandalos was said to have anywhere between $2 million to $4 million. 

Although the story had been one of the biggest stories to come out of Vegas, recent speculations have questioned the very existence of the game. The game supposedly never took place in the Horseshoe, but the Flamingo, and got mixed up with another game that featured multiple players where both the legends participated from time to time. 

6. Jeff Lisandro vs. Prahlad Friedman

In keeping with the public feud theme, Jeffrey Lisandro and Prahlad Friedman’s clash in the 2006 WSOP main event was as entertaining as it was surprising. These players had been the face of the sport in the early 2000s, and when Friedman dished out allegations against Lisandro, things went south really quickly. 

Although an uneasy peace existed between them throughout the build-up to the 2006 WSOP, the battle lines were drawn on the main event.

Friedman accused Lisandro of not posting a 5000 chip ante and called him a thief. Things escalated quickly from there, and at one point, the staff had to separate them as violent threats were being made. 

A replay would show Lisandro putting the ante in, and Friedman would apologize, but their rivalry wouldn’t stop there. Lisandro ended the night three spots above Friedman and went on to win against him in a $10K 2-7 WSOP bracelet years later, ending the rivalry. 

5. Stu Ungar vs. Johnny Moss

Source: X.com

Ever since its inception, Stu Ungar and Johnny Moss are the only two players to have ever won the WSOP main event three times. Their rivalry spanned over many high-stakes showdowns, and some of them are worth remembering to this day. 

The most memorable match-up between the two would happen in the 1981 WSOP heads-up finals, where the young Ungar would defeat the seasoned and respected Moss leaving spectators speechless. However, Moss would have his revenge in the 1990 WSOP main event, where he disqualified Ungar and earned his victory. 

Although their rivalry was never outwardly expressed or talked about as much as some of the more recent ones are, they were on top of the game, and their showdowns were inevitable. Reading up on their history together and as players are definitely worthwhile. 

4. Daniel Negreanu vs. Erik Seidel

Seidel is one of the biggest professional poker players in the southern hemisphere, and Negreanu comes up again as these two definitely didn’t get along. Anybody who watched the 8th episode of Super High Roller would know how tense the situation would get sometimes. 

Their stand-off on the 2013 EPT8 Grand Final Main Event on PokerStars was just a glimpse at their long-standing rivalry.

Negreanu won that particular skirmish, but there are other lesser-known events like the 2011 National Heads-Up Poker Championship Final, where Seidel won, whereas the 2013 Big One for One Drop was won by Negreanu. 

Although they say they have different personalities, some have speculated that as Erki Seidel and Annie Duke are friends, Negreanu simply dislikes Seidel by association. That being said, their rivalry never really died; it entered a stage of cold war and has remained that way ever since.

3. Vanessa Selbst vs. Dan Shak

The rivalry between Vanessa Selbst and Dan Shak goes back to the 2010s. Both of these players have an affinity to win and are not shy to raise the stakes up to millions.

One of the best examples of their rivalry can be seen in the 2014 PCA Super High Roller finals, where they raised the pot up to $3.6 million. Shak won the pot and celebrated with a victory lap. They have also seen clashes in poker tournaments like Super High Roller Bowl and various WPT events. It would seem that both of these players love to take on big pots and seemingly always get in the way of one another. 

Their rivalry continues to this day, and it's hard to say whether or not it will change course. For now, though, they seem indifferent to each other but seem to respect each other’s skills. 

2. Tony G vs. Phil Hellmuth

If a long-standing rivalry with not-so-kind words being exchanged is more your thing, then you definitely must check out the clashes between Tony G and Phil Hellmuth. Hellmuth never seems to get away from challenges, and the old rivalry between Tony G and him was reignited after Tony challenged him back in 2021. 

One of the most memorable clashes between the two was none other than the PokerStars’ TV show called “The Big Game”. After Hellmuth called Tony the “worst player on the table” Tony similarly fired back with “I’m sorry I bullied you”. As this was happening, Hellmuth had already been caught by Tony’s bluff as he likes to undersell his hands. 

Tony would ultimately come out on top, and his treatment of Hellmuth was one of the most entertaining things in poker history. After the call, both would calm down, and Hellmuth would apologize to Tony, but for a moment, the atmosphere was so tense you could feel it from the screen. 

1. Daniel Negreanu vs. Phil Ivey

Once again, Danny Boy and The Tiger Woods of Poker come into our list, the only difference being this time, it's about their rivalry against one another. These players are ranked at the very top not just in the amount of money they have won but also in their skill and determination when it comes to gambling. 

They have clashed multiple times in various tournaments, like their infamous clash on the PokerStars Shark Cage, the EPT Grand Finals, and the 2015 Aussie Millions $250k Challenge, just to name a few. Although both players are talented, Negreanu has won more than Ivey whenever they have played together, and their rivalry is also interspersed with jokes and making fun of each other. 

Another thing to note is that Negreanu has confessed that he believes that Ivey is the better player as he doesn’t fixate on No Limit Hold’em but on all the other games.

Thus, one of the greatest rivalries in Poker is more fan speculation than butting heads. 

Conclusion

Gambling rivalries have always fascinated the crowd to no end. The skill and determination that these players display against each other to determine who’s the best is other-worldly. 

Be it the hands-on pedal-to-the-metal approach taken by aggressive gamblers like Hellmuth and Tony G or the relaxed but tense approach taken by Ivey and Negreanu, these rivalries will always have a special place in all gamblers’ minds. 

Do you have any favorites? Maybe some of the matches reignited that gambling spirit inside of you! Take a look at some under-the-radar gambling games!