Top 10 Worst Bad Beats in Main Event History

The WSOP Main Event is the pinnacle of poker, but it’s also where dreams can be crushed by the cruel hands of fate. Some bad beats go beyond the felt and become legendary tales of heartbreak and disbelief. Here’s a countdown of the top 10 worst bad beats in WSOP Main Event history.

10. Chris Moneymaker’s Bluff Over Sam Farha (2003)

While not a traditional bad beat, this moment is unforgettable for its psychological impact. Heads-up in the 2003 Main Event, Chris Moneymaker bluffed Sam Farha with a missed draw. Farha, holding top pair, folded the best hand, handing Moneymaker a huge pot. This moment shifted the tide and led to Moneymaker’s historic victory, sparking the poker boom.

9. Pocket Aces Destroyed by Two Pair (2018)

Tony Miles, deep in the 2018 Main Event, had A♠A♦ against John Cynn’s K♠J♠. Preflop, Miles was a massive favorite, but the flop brought K♣J♦4♠, giving Cynn two pair. The turn and river failed to help Miles, and Cynn claimed the pot, ultimately winning the tournament and the Main Event title.

8. Greg Raymer’s Painful Exit (2005)

As the defending champion, Greg Raymer was running hot in the 2005 Main Event until Aaron Kanter delivered a crushing blow. Raymer’s A♦K♦ looked strong against Kanter’s A♣J♣, but a miracle jack on the river ended Raymer’s dreams of back-to-back Main Event victories.

7. Doyle Brunson’s Miracle River (1976)

Doyle Brunson’s back-to-back WSOP Main Event wins in 1976 and 1977 were legendary, but his win in 1976 involved a bad beat on his opponent. Brunson held 10♠2♠ against Jesse Alto’s A♠J♠, with Alto dominating. However, the river delivered a miraculous 10♣, giving Brunson two pair and the win. The hand, now known as the “Doyle Brunson hand,” went down in poker folklore.

6. Phil Hellmuth Cracks Johnny Chan’s Aces (1989)

Johnny Chan was looking to win his third straight WSOP Main Event in 1989, but Phil Hellmuth had other plans. Hellmuth’s 9♣9♦ held strong against Chan’s A♠9♠ on a dry board, leaving Chan stunned. While not a traditional bad beat, the loss marked the end of Chan’s historic streak and cemented Hellmuth’s legacy.

5. Jonathan Duhamel Sends Matt Affleck Home (2010)

Deep in the 2010 Main Event, Matt Affleck moved all-in with pocket aces on a board of A♣10♦9♦. Jonathan Duhamel called with pocket jacks. The river brought the Q♦, completing Duhamel’s straight and knocking Affleck out in one of the most emotional eliminations in WSOP history.

4. Gus Hansen’s Quads Crushed by a Straight Flush (2007)

Though not in the Main Event, Gus Hansen’s bad beat is unforgettable. He hit quad sixes on the river, only to lose to Ricardo Brenes’ straight flush. The odds of this happening are astronomical, making it one of the worst beats ever seen.

3. Cary Katz vs. Connor Drinan (2014 Big One for One Drop)

In the $1 million buy-in Big One for One Drop tournament, Connor Drinan had pocket aces against Cary Katz’s pocket aces. The flop, turn, and river brought four clubs, giving Katz an improbable flush and eliminating Drinan in a cooler that shocked the poker world.

2. Jamie Gold’s Pocket Kings Crushed (2006)

Jamie Gold, deep in the 2006 Main Event, was involved in a hand where his A♠Q♠. cracked the opponent’s pocket kings. The river brought an ace, sending Gold home and dashing his hopes of a second WSOP victory.

1. The “Chip Reese Miracle” (1974)

The late Chip Reese famously suffered a brutal bad beat in 1974. Holding pocket queens, Reese was all-in against an opponent’s pocket fours. The flop came Q♣4♦4♠, giving his opponent quads and sending Reese to the rail. The beat was so harsh that Reese reportedly took a break from tournament poker for years.

Final Thoughts

These bad beats remind us of poker’s unpredictability and the emotional highs and lows players endure. While they’re painful for the players, they create the unforgettable moments that make the WSOP Main Event one of the greatest stages in poker history.