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A Brief History of Heads-Up Challenges
Hill Kerby
Writer @Pokercode

It's a tale as old as time and we've all done it. One on one, face to face, mano a mano. Or how we call it in poker: heads up. Pokercode Founder Fedor Holz is taking on the infamous Wiktor 'Iimitless' Malinowski and we are taking a look at the (recent) history of who did it before them.

Click to read all you need to know about Fedor vs. 'Iimitless'.

High Stakes Feud: Doug Polk vs Daniel Negreanu

📊: Two tables of $200/$400NL online

🕑: 25,000 hands across 36 sessions over a three-month period (Nov 2020-Jan 2021)

🏆: Doug Polk

The history of this pair goes back to 2014, a time when Doug Polk was arguably the top online heads-up no-limit cash game player in the world. Daniel Negreanu had just taken second place in the WSOP “One Drop” event and in the process, had some of his play criticized in a manner that ultimately led to Negreanu asserting that he was willing to bet a million dollars on the fact that he could beat $25/$50NL 6-Max on PokerStars within two weeks’ time.

Polk fired back, saying despite everything Negreanu had accomplished to date in his career, that such a claim was naive given the evolution of high-stakes online 6-max cash games. A year later, Negreanu, largely the face of Team PokerStars at the time, backed PokerStars’ decision to remove its Supernova Elite VIP tier in a manner that was dubbed by a large part of the poker community as: 'More rake is better.'

(This sentence was also blasted on a billboard right outside Rio Las Vegas for the 2018 WSOP as an advertisement for 'MoreRakeIsBetter.com').

Several other exchanges occurred through the years, and eventually come 2020 Negreanu was in the spotlight for his inability to handle Twitch trolls while streaming during the online version of the WSOP. Polk had largely been retired from the game, but saw an opportunity to enter the limelight and further rekindle the fire, officially challenging Negreanu to a heads-up battle that Negreanu accepted.

After a few months of back-and-forth, terms were agreed to by both sides and the match began on November 4th, with the two playing the first round live. After 200 hands, Negreanu was up $116,500. Each player saw ups and downs over the first eight sessions, trading the lead with one another until Polk finally took off and never looked back, ultimately taking more than $1.2 million off of his long-time foe.

The High Stakes Feud between Daniel Negreanu and Doug Polk ended with Polk on top, winning over 1.2 million dollars.

Andy Beal vs The Corporation

📊: $10K/$20K up to $100K/$200K Limit Hold’em

🕑: 2001-2004; 2006

🏆: The Corporation

Andy Beal, a Texas banker largely regarded among the elite as a 'whale' was fairly well-known in the nosebleed stakes of live cash games that often took place in Las Vegas during the early part of the millennium. He eventually found his way into heads-up matches against some of the best players in the world, playing heads-up Limit Hold’em at stakes ranging from $10K/$20K up to $100K/$200K.

Some of the players Beal went toe to toe with included Doyle and Todd Brunson, Chip Reese, and Gus Hansen among others. At one point, Beal was up over $10 million against the group known collectively as 'The Corporation' but ultimately wound up losing around $16 million between 2001 and 2004, leaving him swearing he would never play poker again.

Two years later, Beal returned to face another member of The Corporation: Phil Ivey. Ivey and Beal went to battle at the Wynn, Las Vegas, for three days starting with $30K/$60K limits and ultimately raising them to $50K/$100K. When all was said and done, Ivey took $16.6 million from Beal. It was rumored Beal had made $10 million earlier that same month from The Corporation, but no matter how you add it up, The Corporation came up on top.

The story of Andy Beal vs. The Corporation was written down by Michael Craig in the book 'The Professor, the Banker, and the Suicide King - Inside The Richest Poker Game Of All Time'.

Andy Beal, the businessman who took on a group of the best poker players.

Durrrr Challenge

📊 Online: Four tables, minimum $200/400 NLH/PLO

📊 Live: $500/$1,000 NLH/PLO

🕑 Online: February 2009 to ???

🕑 Live: 17-19 November, 2009

🏆: Dan 'Jungleman' Cates; Tom 'Durrrr' Dwan; Marcello 'luckexpress' Marigliano

The 'Durrrr Challenge' was a series of heads-up matches offered by Tom 'Durrrr' Dwan in response to his struggles to receive action at the highest stakes of online poker. In it, he offered 3:1 odds on a side bet in which he put up $1.5 million to any challenger’s $500,000 over a minimum of 50,000 hands. The only exception was Phil Galfond, who was excluded from participating in the challenge by Dwan.

Patrik Antonius was the first taker and wound up losing more than $2 million over 40,000 hands in a 16-month span with Antonious eventually conceding.

Amidst that time, Dwan also took the challenge live, playing a series of three live matches in London that each consisted of a $250,000 buy-in and stakes of $500/$1,000 in November 2009.

First up was Marcello 'luckexpress' Marigliano, who finished the match up $22,500. Dwan then won match number two against Ilari 'Ziigmund' Sahamies, finishing up $68,000 over a 12-hour match. Dwan then came up massively in the third and final match, taking $750,000 off of Sammy 'Any Two' George to ultimately win two of three matches for $795,500 in total profits.

Part two of the challenge began in 2010, with Dwan set to face Dan 'Jungleman' Cates. Cates wound up taking more than $1 million in $200/$400 NLH in under 20,000 hands before the match appeared to stall out. Dwan allegedly became harder to reach, and by 2013 the two only played another 1,500 hands with Cates making another $200,000 off of Dwan.

As of 2021, the challenge has still not been finished. There is uncertainty as to if the match will ever be concluded (or if Dwan already forfeited/bought himself out, for that matter), and Doug Polk has even gone as far as calling the challenge the biggest scam in poker history.

Tom Dwan - Photo by Danny Maxwell (PokerNews)

The Galfond Challenge

📊: $100/$200 up to $150/$300 pot-limit Omaha

🕑: 2020 - ???

🏆: Phil Galfond

Phil Galfond was the only player excluded from the original 'durrrr Challenge'. Fast forward a decade later to 2020 and Galfond’s 'Run It Once' brand had its own poker site up and running. He used his platform to create the Galfond Challenge, where he would play a series of heads-up matches at various high stakes against some of the six different challengers.

First up was 'VeniVidi1993' a player only known by his online screen name who's been active in the high stakes PLO scene since 2016. The two played €100/€200 PLO for 25,000 hands with a side bet that saw Galfond put up €200K to his opponent’s €100K. Galfond quickly fell behind in the match and he even dropped down to - €900,000. He slowly started the climb back up, but he stayed in the red until less than 3,000 hands remained in the challenge. Galfond entered the final session down just over €30K, but was able to pull off the come-from-behind victory, finishing up just €1,671.58 when all was said and done, winning the extra €100,000 from 'VeniVidi1993'.

Ioannis 'ActionFreak' Kontonatsios was then defeated to a tune of almost €115,000 over the course of 15,000 hands at €150/€300 PLO in which he also won their even-money side bet of €150,000. After that, he made quick work of Chance Kornuth, who conceded after 25,400 hands of the 35,000 set to be played at $100/$200 PLO. Galfond won $726,500 in addition to the $250K side bet that Kornuth put up with 1:4 odds to Galfond’s $1 million.

Galfond is now playing Bill Perkins and is currently up a hair over $90,000 over just 862 hands at $100/$200 PLO. Like with Kornuth, Galfond has put up a cool milly to Perkins’ $250K with a set duration of either 50,000 hands or a $400K loss, whichever comes first. Galfond is also set to play both Daniel 'Jungleman' Cates and Brandon Adams as his final two challengers for the series.

Phil Galfond, the man who was excluded from playing in the 'Durrr challenge'

Phil Galfond

The Superstar Showdown

📊: $50/$100 no-limit hold'em and pot-limit Omaha

🕑: 2010 - 2012

🏆: Viktor 'Isildur1' Blom

The rise of Viktor 'Isildur1' Blom is one that will not be quickly forgotten. The young Swedish player rose to fame by playing his hyper-aggressive style and having the biggest swings ever recorded. On December 8th, 2009, Blom played Brian Hastings for five hours when he lost $4,200,000, making it the largest recorded loss in a single day in the history of online poker, according to HighStakesDB.

When Blom joined PokerStars as a sponsored pro the operator issued a the 'Superstars Showdown' and challenged every poker player in existence to take on 'Isildur1' in a heads-up match. The terms were to play heads-up against Blom for 2,500 hands with stakes of $50/$100 and a cap of $150,000.

The first taker was none other than Ike Haxton. Haxton managed to secure a win of $41,701 over Blom and it wasn't exactly the start he imagined. Luckily for Blom, Haxton would come back over a year later to continue their challenge.

In the meantime, Blom played against the likes of Tony G (+$44,820), Daniel 'Jungleman' Cates (+$51,196), and Eugene Katchalov (+$111,750). Blom also played qualifier 'DaddyFish72'. The qualifier won an $11 satellite and received $15,000 to play Blom at $5/$10 stakes. This match turned out to be the smallest win of the challenge for Blom, as he won only 1 big blind.

Continuing with stakes at $50/$100, Blom played Negreanu twice (+$123,500), 'urnotindangr' twice (+$55,755), 'Mastermixus' (+$1,279), Rui Cao (+$150,000), 'Terken89' (+$150,000), and Alex 'Kanu7' Millar (+$37,687).

About a year later, Ike Haxton wanted to up the stakes. He played another set of 2,500 hands against Blom with $100/$200 blinds and this time Haxton ended on top again for a win of $5,093. While most challenges stopped after 2,500 hands, Haxton and Blom decided to raise the stakes yet again to $200/$400 and to play with a cap of $500,000 to play a $1,000,000 match. It took Blom 3 days to end on top, winning the full $500,000 from Haxton ending at an overall $453,206 win against Haxton.

Blom didn't play any challengers after the match and ended up well over $1,000,000 in profit from these challenges.

Viktor Blom

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