4 Worst Bad Beats in High-Stakes Live Poker Tournament History

Drinan’s recent drubbing at the hands of Katz was a bad beat, but was it the worst? Here are some of the baddest beats in history.

During the World Series of Poker’s annual $1 million buy-in event on Tuesday American poker pro Connor Drinan went down on what gambling news have called “the biggest bad beat in history.” We’ll fill you in on all of the details later, but the point is that Drinan lost his entire $1 million stack on a single hand, bowing out in the early stages of the tournament.

Drinan’s downfall was crushing, but certainly there have been other colossal collapses in the world of poker, some for the money involved, and others for the sheer unpredictability of the outcome. What are the worst beats in live poker history?

Chris Moneymaker vs Phil Ivey, 2003 WSOP Main Event

• Connor Drinan lost his entire $1 million buy-in in a single hand against Cary Katz

• Amateur Chris Moneymaker beat celebrity poker player Phil Ivey to become a champion

• Danny Nguyen had a 1/200 chance but beat ShandorSzentkuti to win in 2005

This was the poker hand that turned Moneymaker from amateur to celebrity overnight and helped turn poker into a major media event in the US. How did it go down? Moneymaker was dealt an Ace-Queen and raised on the flop; Ivey called with a pair of nines.

The flop gave Moneymaker trips Queens, in hindsight making him look near unbeatable. Then something astounding happened. The turn showed a nine, giving Ivey full house; unbeknownst to Moneymaker. Moneymaker raised; Ivey went all-in; the final showdown ensued.

The river brought up an ace! Moneymaker’s full house beat Ivey’s, one of the most astounding conclusions to a poker hand imaginable. The amateur upstart beat the already celebrity poker player, and a new poker star was crowned king.

Doyle Brunson vs Jesse Alto, 1976 WSOP Main Event

This epic bad beat brings us back to almost-prehistoric times, the days when poker was still the game of cowboys and back country gamblers and Texas Hold’Em was a new addition to American poker rooms. Two casino cowboys, Doyle Brunson and Jesse Alto, went toe-to-toe in the second World Series of Poker Main Event in Las Vegas.

“Texas Dolly” Brunson was the chip leader going into the fateful hand against Alto. After the flop Alto had the top two pairs(Jacks and Aces) and Brunson the bottom pair tens. Not realizing his position Brunson went all in, hoping to push Alto to fold.

Much to his dismay Alto called, and while the turn brought a deuce to give Brunson two pairs of his own, he still trailed Alto. That was when the Texas legend called in a miracle. The river brought him a ten, giving him the trumping full house and his second WSOP bracelet. To this day, the ten-deuce full house is still referred to as “the Brunson.”

Danny Nguyen vs Shandor Szentkuti, 2005 World Poker Tour Bay 101 Shooting Stars

If there was ever a case of someone pulling victory from the jaws of defeat, it was this. Former poker dealer Nguyen opted to be bold and go all in with his Ace and seven pocket. Szentkuti called him with Ace-King, and what followed was one of the most improbably beats ever.

The flop brought home a King and two fives, giving Szentkuti two pair a 99.5 percent mathematical chance of winning the hand. Then the turn brought a seven, given Nguyen a bottom two pairs. Miraculously, the river brought another seven, given Nguyen a full house and a victory over his stunned opponent.

Doing the math, Nguyen had a 1/200 chance of winning that hand. He went on to beat the other five opponents at the table and win the entire tournament. None of which would have happened if he hadn’t landed that lucky seven against Szentkuti.

Connor Drinan vs Cary Katz, 2014 WSOP Main Event

The well-publicized event on Tuesday may well be the “biggest bad beat in history.” After receiving their cards Cary Katz raised pre-flop. Holding pocket aces, Drinan decided to go for a big hit and go all in. Katz called, and both players put their hands on the table. Katz held pocket aces well.

The outcome of this hand would come down to a flush. The flop brought two hearts to the table, which combined with Katz’s ace of hearts to give him three. But no stress for Drinan. The hand looked like it would finish in a draw, with the pot divided and the two players going back to the drawing board.

That’s when things got very interesting, and Drinan’s bid for an $18 million pot began to unravel quickly. The turn landed Katz another hearts, putting him one step closer to a flush. But what’re the chances of someone with an off-suited pocket after winding up with a flush?

Call it a miracle for Katz and a nightmare for Drinan. The river brought a fourth consecutive heart and flush for Katz. Drinan said goodbye to his entire $1 million buy-in and his bid for a WSOP bracelet. Talk about heartbreak. As happy as we are for Katz, our emotions are all used up on sympathy for Drinan.