Over the last 15 or 20 years, no card game has captured the public’s attention quite the way Texas Hold ‘Em has; the game has even become a popular watch on television. Essentially, in a five-card hand, each player is dealt two cards, with five more cards (three at once being the Flop, then one called the Turn, and then the River) being dealt face up one bet at a time. Between what’s on the table and the two in their pockets, players take the best five-card hand. The opportunities for bluffing make it even harder to figure. Throw in blind or double-blind bets, and you’ve got a high-stakes card game. Exhalted as the big victories are, the defeats can be quite crushing, understandably. A “Bad Beat” hand refers to a jackpot in which the loser really had a great-looking hand, despite all indications he would win, and the bulk of the jackpot going to the loser; sometimes the casual term “bad beat” just means you got wiped out. Either way, the following are some of the worst “bad beats” ever seen in Texas Hold ‘Em.

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Double Quads, Live at the Bicycle.

The Bicycle Casino is the scene for this incredible round of poker, with both the winner and the loser holding four of a kind. Either one of the players could have reasonably expected to win – and in this case, both of them did! The presence of “double quads” kicked in the Bad Beat Super Jackpot. With $100,000 total at stake, the “winner” (who had four Queens) took home $25,000, while the “loser” (with four Threes) raked in $50,000. The remaining $25,000 gets divided up between all the other players who were dealt into the hand initially.

Danny Nguyen Gets His.

Before the final card was dealt, legendary pro Danny Nguyen was looking at two pair (Fives and Sevens), while his opponent was staring at those same Fives and a pair of Kings. The chances of of the last card being turned coming up a 7, given the cards that were already on the table, were one in 274. It popped up, and Nguyen became about half a million dollars richer. With his nerves of steel, Nguyen looked like he expected it the whole time.

Daniel Negreanu Takes a Bath.

Veteran gambler Gus Hansen found himself squared off with Daniel Negreanu – the Bobby Fischer of poker – in a classic poker-face bluff fest, televised on High Stakes Poker no less, with hundreds of thousands of dollars in the pot: Negreanu gives a big sigh, Hansen digs crumbs of out of his tear duct, they both bet their banks and then… Negreanu turned over a full house. Hansen had been sitting on Quad Fives ever since the Turn and was just soaking the over-confident Negreanu the entire time.

Phil Hellmuth Goes Off.

Phil Hellmuth, a former World Series of Poker champion, is running his mouth as usual in this classic poker beat-down. From the Flop on, he keeps trying to run his opponent off the table with brash attitude and big bets. Brian Brandon, preternaturally sure that Hellmuth is sitting on “a middle pair” and is bluffing, holds on until the end. The River gives him a third Seven to go with the one he’s been sitting on and the first card in the Flop. When he calls the big-shot bluff master, he wins big, but the best part by far is watching Hellmuth lose his composure at the end.

Phil Ivey Hits the Jackpot.

Ice-man Phil Ivey wound up on the winning end of a huge payday when he played high-stakes betting machine Patrik Antonius, an equally stoic card-sharp. Ivey’s River bet elevated the pot to over $550,000 – and no wonder, since he was looking at a Full House with Jacks over Aces. Antonius, knowing he only had three Aces to his name (two of which were in the Flop), called anyway. When they both showed their cards, Ivey’s total single-hand winnings cleared $800,000. A record at the time, it cemented Ivey’s standing in the world of professional high-stakes poker.

Million Dollar Shootout.

The diminutive but intrepid Tom Dwan wound up playing in one of the most exciting poker hands anybody’s ever seen. Post-Flop, he was sitting on the King and Queen of Spades, with the professorial Barry Greenstein holding a pair of Aces. On the table sat the flop, an enticing Queen, a Four and Deuce – both Spades. Before the Turn, Greenstein bets Dwan “all-in”. With the pot sitting at $919,600, the 22-year old Dwan declined to pull back $200,000 of his wager, and up came the cards. The Queen at the turn made the River’s Seven irrelevant, and Tom Dwan won the biggest pot in the history of televised poker (at the time), with three Queens beating Greenstein’s winsome pair of Aces.

Get the Money on the Table.

In this Full Tilt classic, even before the Flop, there are two things the viewers notice about Phil Ivey. One, he’s so emotionless as to make a Vulcan look like a cheerleader. Two, he wants to jack up the pot on this hand early, because he’s been dealt an Ace-Deuce and he knows that his opponent, Tom Dwan, likes to bite on the big bets (unaware that Dwan has the Six and Seven of Hearts in his pocket). The Flop helped each of them a little, but the Turn came of the Four of Hearts, giving both of them a five-card Straight before even seeing the River. Ivey coolly pushed $90,000 into the kitty; Dwan saw that and then raised him another $142,000. Without so much as a facial tic, Ivey went all-in. With $1.1 million on the table, the River turned an irrelevant Jack, and Tom Dwan once again became the richest single-hand poker player in televised history. Ivey’s typical goldfish-esque reaction: “Wow, good hand.” He had just lost half a million dollars.