Chris Moneymaker had the Bluff of the Century in 2003. This past week, Doug Polk had perhaps the Failed Bluff of the Century.

On Sunday, heads-up for a bracelet, Polk bluffed off a significant portion of his stack at the 2023 World Series of Poker (WSOP) less than one week after his infamous bluff attempt that didn’t get through on Hustler Casino Live’s $1 million game.

In both instances, the Upswing Poker founder had a busted draw and attempted to use aggression to coerce his opponents into folding somewhat marginal holdings in massive pots. Both times, however, his efforts were unsuccessful and quite costly.

Losing a $1.1 Million Pot to Tom Dwan

During the fourth and final day of the big games on Hustler Casino Live, Polk played one of the most memorable hands ever in live-stream poker history against Tom Dwan.

The hand began with Polk raising to $3,000 from the cutoff with 5♠4♠ and then calling a three-bet to $14,000 from “durrrr” and his 7♥7♣ in the small blind.

When the flop came 2♠7♦K♦, bingo for the preflop aggressor, Dwan bet out $15,000 and his opponent called, hoping to either pick up some equity on the turn or bluff to take it down. The 6♥ was juicy as it gave the co-owner of The Lodge Card Club near Austin, Texas an open-ended straight draw. But Dwan bet out $30,000, about half the size of the pot.

Polk then bumped it up to $115,000 on his draw, and this is where the hand got a bit strange. Sitting on the second nuts, Dwan went into the tank for quite some time, an odd play. The only hand that had him beat was pocket kings, and that wasn’t a likely holding for his opponent given he didn’t four-bet preflop.

After a few minutes of waiting, Polk had enough and called the clock. Shortly after, Dwan made the call and the 6♠ showed up on the river, giving “durrrr” a full house. He decided to slow-play his hand and checked it over to the button.

Polk, who couldn’t possibly win the $291,000 pot without betting, refused to surrender to the former online poker star and ripped off a bet of $420,000, leaving about $550,000 behind.

There was no way Dwan would fold as he was only concerned with pocket kings or possibly pocket sixes, both unlikely scenarios. Once again, he oddly went into a deep tank before deciding to just call.

Did it Cost Doug Polk a Bracelet?

The first failed bluff cost Polk more than $500,000 with just five-high, but the second one was quite different given that it took place during a tournament instead of a cash game.

In the sixth and final round of WSOP Event #8: $25,000 Heads-Up No-Limit Hold’em Championship, Polk had built up a relatively comfortable lead against Chanracy Khun. First place was set to pay $507,020 in the 64-player tournament, and the runner-up would take home about $190,000 less.

With the blinds at 80,000/160,000, Khun limped the button with 8♠6♣ and then Polk checked Q♦4♦ to a flop of 5♣6♦3♥, top pair for the button and an open-ender for the big blind.

Following a check, Khun bet 160,000 and received a call. When the K♣ appeared on the turn, action again checked to the button who bet 250,000. Polk opted for a check-raise on his draw to 900,000 but was unable to convince his opponent to fold.

Off to the river they went, which was the 9♥, no improvement to either player. Knowing that queen-high couldn’t win at showdown, the heads-up no-limit hold’em legend put Khun to the test for his entire 2.34 million stack.

After some thought, Khun made the brilliant call with third pair and took down the most crucial hand of the match. His stack was up to 7.1 million, while Polk had dropped down to under 2.5 million or about 15 big blinds. Shortly after, Khun took down his first WSOP bracelet, denying Polk his fourth.

While Polk hadn’t officially lost the tournament following the failed bluff, it put him in a deep hole that he couldn’t overcome. And while you could also argue there never was a guarantee he would have won if not for bluffing off so much of his stack in the first place, for all intents and purposes, Polk lost around $700,000 this past week on two bluffs-gone-wrong.

The good news, for the popular YouTuber, is that he isn’t a results-oriented poker player, and the money he’s won lifetime from bluffs just like these have likely exceeded the money lost in his failed bluffs.