It's hard to put this story in perspective, and very hard to relate to, especially given that I cashed for $192k in a tournament in the midst of an extremely profitable year for me, but it was such a soul crushing experience that I was sick for a week afterwards. Outside of Black Friday (https://steemit.com/anarchy/@daut44/forced-to-move-away-from-usa-to-continue-a-career-pro-poker-stories-part-1), which forced me to move away from the US to continue playing poker for a living, this is the story of my most painful moment in poker.

I wrote a previous blog on my experience winning over $1.5M in a poker tournament in January 2007: https://steemit.com/money/@daut44/what-it-was-like-to-win-usd1-500-000-in-a-poker-tournament-at-age-22

The final 6 was the complete opposite from last time around

I want to transition from my favorite poker experience, winning a huge tournament, into blogging about the more painful sides of poker by starting with a positive winning story first before delving into topics such as extended losing streaks, being stolen from/scammed, or having to transition away from poker due to higher profitability elsewhere.

I think my journey through this televised World Poker Tour (WPT) event is more interesting than my win in January of that year, and the emotions and schadenfreude I felt after navigating my way through a 6 day tournament to fall just short of the really huge money are more insightful than coasting through a tournament with good luck.

In December of each year, the Bellagio in Las Vegas runs a tournament series they call the Five Diamond. It's a string of ~15-20 tournaments culminating with a $15k buyin WPT. I played 6 or 7 events leading up to the main event, entering roughly $12000 in buyins and cashing for about $4000, so I was down after the first few weeks of the trip.

After the main event, I wrote a long blog describing key hands I played on each day of the 6 day tournament. It contains a lot of poker shorthand, and is geared towards people who speak poker fluently so it will be incomprehensible to casual readers out there, but some of you will enjoy the details: http://www.cardrunners.com/blog/Daut44/Interesting-hands-from-5-diamond

For those that play poker seriously, it’s also fun to note the changes the game has gone through in the last 8.5 years since I played it. Reading through some of these hands makes me eye roll now because in 2016 they would be horribly played, but at the time I thought I played them perfectly. It’s a microcosm of the Dunning-Kruger effect:

I am a much stronger player now but have less confidence in my abilities than I did in 2007. The lesson to take away from this is never stop learning or striving for greater proficiency, no matter how skilled you think you are there is room for improvement.

Day 1

My day 1 starting table was more recognizable than it was in PCA earlier that year. There were a few businessmen present, a few less skilled young internet players (nowadays they are all highly skilled), a few well known live professionals such as Humberto Brenes and Andy Black, and an actress named Jennifer Tilly.

Humberto is known for his outgoing personality, his conservative play at the table, and a tiny shark toy he carries with him at all times:

Humberto plays a psychological game: he only plays strong hands but is loud and perpetually involved in table discussion, which is an attempt to convince players he is looser and more aggressive player than he actually is.

Andy Black is an Irish poker player best known for final tabling the World Series of Poker (WSOP) main event in 2005, finishing 5th for $1.75M:

Jennifer Tilly is an actress. IMDB page: http://www.imdb.com/name/nm0000236/

She started dating professional poker player Phil Laak in 2004 and became a fan of the game. She won the WSOP ladies event in 2005 for $158k and still appears at the WSOP each summer and plays poker frequently.

Everyone started the main event with 30k in chips and I had a bit of a roller coaster day. I peaked at 35k in chips, at one point was very short stacked with about 11k in chips, but ended the day with 22k. My most notable hands were against Humberto, who as described above, tried to be loud and in my face at multiple points but always ended up having an extremely strong hand.

Be Careful What You Say Out Loud

An embarrassing side story for a friend that will go unnamed: after the day finished, a loudmouth buddy of mine wanted to grab dinner. He was around the table for the last 10 hands of the day, and after we bagged up our chips (literally put your chips in a sealed bag to be opened at the start of the following day), we walked up to his room to chill out and smoke some weed before heading to dinner.

As we are walking down the hall of his floor, out of nowhere he says “Man, Jennifer Tilly really let herself go huh?” I remember watching her movie Bound when I was middle school and Jennifer was the epitome of sexy: confident, gorgeous, and she had a sultry, raspy voice that was too much for a 12 year old to handle. 11 years later, I still thought she looked great, but apparently my friend disagreed. I turned to look at him and as I do I see Jennifer out of the corner of my eye: she was staying on the same floor and had taken a different elevator up. She likely heard the comment, and he got to walk around the remainder of the day feeling like the jackass that he is.

Day 2

Day 2 I drew a contradictory table: on one hand, it had more professional players than the day before, but on the other, they were predictable conservative players that I could exploit.

You see back then the ratio of professionals to recreational players was much lower than it is today. Combine that with the strategic aspects of poker essentially being in their infancy in 2007 and it was much easier to win. Many professionals were not great players, but were simply patient and disciplined enough to wait for premium holdings and profit off recreational players who weren’t paying enough attention to notice these pros always had strong holdings. However, the strong professionals were much more aggressive and able to easily outmaneuver the weaker professionals, which often times made a table of weaker professionals easy to play against.

I began day 2 by just trying to claw my way back into a playable stack.

A photoshop of me as Napoleon Bonaparte, because, you know, my chipstack was very short

I bled away some chips early in the day but then doubled my stack up to 28k when my Ace King (AK) beat the pocket tens of another player. I picked up momentum, won more pots, doubled up again with pocket kings, and won the majority of pots at the table to close the day with a table leading 89k. Despite the average stack being roughly 120k to end the day, much more than anyone at my table had, I felt extremely confident after playing my best and more than 6x’ing the amount I had at my lowest point.

Day 3

My Day 3 table was the opposite of Day 2. Replacing weaker professionals were some of the strongest players in the world. Although I was maybe a better cash game player than some of my opponents, I was probably the 4th best tournament player at my 9 man table to start day 3. Two of my good friends (and top online players) were there and probably the most famous poker player in the world, Daniel Negreanu, was present with a lot of chips.

To make matters worse, I was short on chips relative to the table(89k vs a table average of roughly 175k), and we were closing in on the money: 664 players bought in for $15000 each, and the top 100 were guaranteed at least $28,905. The person who finished 101st would get nothing and the person who finished just after in 100th would get nearly $30k, a huge pay jump.

I won a big pot to start the day to nearly double my stack, but quickly lost back the chips I gained in a series of other hands. Once my stack fell below 80k, I was forced to play very close to the vest because making the top 100 is so important: finishing 100th was the same payout as finishing 51st. Immediately after the 101st player left was eliminated, I doubled up to 140k and then slowly grew my stack til it reached its peak of 270k to end the day. 44 players moved on to day 4, and everyone was guaranteed $38,545.

Day 4

I drew another difficult starting table on day 4 with a few of the best online and live players in the world: Mikael Thuritz, Erick Lindgren, Daniel Alaei, and Peter Jetten. The day began the same as day 2: I lost a few pots before doubling up and acquiring a playable amount of chips. After the double I picked up some hands, gained momentum and built my stack to about 1.1 million before switching to a new table.

I pick up my stack, walk over to my new table, and see Gus Hansen on my immediate left. Gus is a poker and backgammon legend. Before Gus, almost everyone was straightforward and conservative. Gus burst onto the scene a few years prior, winning many tournaments by being extremely loose and aggressive with an emphasis on the mathematical side of poker. He singlehandedly inspired many people to play a different style.

While Gus played too loose and aggressive compared to optimal play, there were still many things to be learned from his play. He is deliberate, often taking more time and opening his mind to creative possibilities that other players mindlessly dismiss. He is scary: any time you enter a pot you know you will have to contend with Gus fighting for the hand, which convinces most players to tighten up and fold more hands, which in turn gives Gus many easier wins with less resistance. But at this table, he played too many weak hands and bled most of his stack off within an hour.

Since Gus was now short stacked and I had a lot of chips, I started playing more aggressive. I raised a mediocre hand, King Jack (KJ), in early position, Gus went all in for not too much more, and I instantly called, knowing that I was getting correct odds to call with anything I had against an aggressive player. Gus seemed upset due to how quickly I called and concernedly turned over Ace King of spades (AKs), a hand that was roughly 74% against what I had. Fortunately for me, 74% is not 100% and this happened to be in one of the 26% of the time where I win the hand, boosting my stack to 1.5 million.

After that everyone greatly increased their aggression levels. Huge raises preflop, lots of reraising, and I didn’t have any strong hands to take advantage, so my stack slowly decreased and I ended the day with 1.24 million, in 9th place with 18 players remaining and guaranteed to cash for at least $77,085.

Day 5

Let’s take a look at the payouts for the final 18 players:
1st: $2,482,605
2nd: $1,252,640
3rd: $674,500
4th: $433,675
5th: $289,070
6th: $192,715
7th: $173,445
8th: $154,170
9th: $134,900
10th: $115,630
11th-15th: $96,355
16th-18th: $77,085

The payouts increase gradually until the final 6 then increase rapidly afterwards. My table was a mixture of top pros, weaker pros, and recreational players.

Very early in the day, I won a huge hand vs Daniel Negreanu to knock out a player and take the chiplead.

This was the live update from www.cardplayer.com:

Incredibly lucky: AA v KK is the ultimate spot to be in, and having a 3rd player in the hand with a king in his hand further increases my chances of winning the large side pot because there is only one king left in the deck for Daniel to make three of a kind, and the jack in Peter’s hand also lowers the odds Daniel makes a straight. Without the dead king and jack, Daniel’s hand would normally be 17.82% to beat mine, however, with those cards out his odds dropped to 9.6%.

After that hand, I slowly chipped up and coming into the final table of 10 I was 2nd in chips with 3.575 million. Here were the final 10 with the chipstacks:
Seat 1 - Ken Rosen - 1,405,000
Seat 2 - Ted Kearly - 2,750,000
Seat 3 - Erick Lindgren - 1,230,000
Seat 4 - Raymond Davis - 1,360,000
Seat 5 - Jimmy Tran - 1,350,000
Seat 6 - Jordan Rich - 4,185,000
Seat 7 - Eugene Katchalov - 2,110,000
Seat 8 - Ryan Daut - 3,575,000
Seat 9 - David "Devilfish" Ulliott - 1,590,000
Seat 10 - Matthew Casterella - 625,000

I’m going to go on a little tangent here regarding equity. Everyone remaining was guaranteed at least $115,630, however, everyone’s stack had equity. I plugged the payouts and chipstacks into an Independent Chip Modeling (ICM) calculator, which calculates how often players finish in each position based on their chipstack and then calculates how much the stacks are worth.

Here are the ICM values of each player:
Ken Rosen: $478,876.84
Ted Kearly: $746.517.71
Erick Lindgren: $439,397.24
Raymond Davis: $468,848.54
Jimmy Tran: $466,608.66
Jordan Rich: $980,237.43
Eugene Katchalov: $626,219.76
Ryan Daut: $886,274.81
Devilfish: $519,259.19
Matthew Casterella: $291,109.84

So the shortest stack player’s equity was nearly $300k and mine was nearly $900k. I was in a fantastic position, particularly with Erick Lindgren (one of the best in the world at the time) shortstacked and most of the other top players eliminated from 11th-26th place: Vivek Rajkumar, Gus Hansen, Mikael Thuritz, Huck Seed, Peter Jetten, Todd Brunson, Negreanu, and John Monnette. That is an extremely impressive list of players with close to 50 million in lifetime earnings who all busted before this point. Erick was eliminated soon after, and I was confident that I was the best player remaining with 9 left and a lot of chips.

With 7 players left, my stack was likely worth just over 1 million dollars. One of my good friends, Steve Billirakis (know as mrsmokey1 online), offered to buy a large piece of me going forward, valuing my stack at $800k. I was confident in my ability and thought my stack was worth way more so I turned him down. Immediately afterwards everything started to go downhill.

First I lost this hand to Eugene Katchalov:

I was 70% to eliminate him and enter the final table 2nd in chips, but Eugene was the one to get lucky here. The loss didn’t phase me, I still had over 2 million chips, was in the middle of the pack, and there were a few people with very short stacks who were close to being eliminated.

But a few hands later I made a big mistake:

I definitely should have just called preflop, but I thought I had a read that Devilfish was being deceptive and raising a wider range from early position and went with it, but it was an unnecessary move. This loss left me with 1.1 million remaining and I was pretty angry and upset with myself. There was still a player shorter stacked than me, but my equity had gone from over a million to probably around $400k in just a few hands.

A few hands later I lost another all in, this time it was close to a coinflip situation. I guess I was lucky to lose it to the one player shorter stacked than me, but I was left with very few chips and in a spot where I would be looking to get it all in quickly before the forced blinds ate up my stack. Fortunately for me, another player was eliminated just before the blinds hit me, so I limped into my second televised final table with just 4 big blinds.

Found this interview of me before the final table, I look absolutely miserable

Day 6

I wish there was a story of a great comeback, but unfortunately I set an unbeatable record and was eliminated on the first hand of the final table with another coinflip situation, AJ vs pocket eights. I cashed for $192,715 and was completely devastated to cash that far below my equity from 7 left. Not only was I devastated, but I was left with a feeling of jealousy and schadenfreude, hating the players who outlast me and wishing them pain. Soon after I busted out, Jordan Rich finished in 5th place by playing a hand very badly and at the time it gave me some solace to know I wasn't the only one. Eugene is an incredible human being and there is nothing bad you can say about him, but I was so jealous of his win and it further deepened my short term misery.

I want to dive into a pet peeve of mine, which is a misunderstanding of the difference between jealousy and envy. Envy is when you want something that someone else has, for instance I am envious of Aaron Rodgers for being the best quarterback in the world and dating Olivia Munn. Jealousy is when you feel someone is taking something away from you to their gain. Eugene beat me in a large hand where I was a huge favorite and ended up winning a tournament that I felt I should have been winning. Jealousy is a much stronger and insidious emotion for me.

Who could be angry at this man? What a bitter baby 2007 Ryan was

No one bad luck hand did me in and I didn't punt off my chips, it was a combination of one iffy play (the AJ hand vs Devilfish) and 3 unlucky losses in a row.

It was the combination of everything that really got to me

-that I finished exactly 6th, the last spot of the flatter payouts before they really got big. 1st place was 13 times my payout, 4th place was over double my payout, but 6th place was less than double 15th place.
-that i lost a 70/30 with 7 left to the eventual winner, Eugene Katchalov.
-that the final 9 players were relatively weak compared to the final 26: Vivek Rajkumar, Gus Hansen, Mikael Thuritz (one of the best 8 game players in the world), Huck Seed, Peter Jetten (great NL player), Todd Brunson, Negreanu, John Monnette, Erick Lindgren all bust between 26th and 10th, and at the time I thought I was the best player remaining (Eugene Katchalov is a fantastic player, but I didn't know him at the time)
-that no one big hand did me in, but rather 4 hands all in preflop

I flew home and laid in bed for a week before feeling better. I despise bad beat stories and despise complaining about bad luck in a game of skill, particularly in a year where I won one of the bigger tournaments that ran, but I've never felt so soul crushed by anything. Poker is a tough game to deal with the mental swings, even for those who have been lucky and are doing well.

After a week I was able to better put things in perspective, was over the bad finish and happy for the other people who won big, but I still significantly decreased the amount of live tournaments I played and stuck to lower variance outcomes where my equity would never swing over $500,000 in the span of a few hands from that point forwards. Just as I could have been eliminated on day 1 of the PCA I won, who knows what heights my poker career reaches if I finish higher, am not dismayed and continue to play many tournaments? Poker is a funny game, and to truly be the best you need to be extremely confident and head strong when dealing with loss. I always thought I could take losses in stride, but what I didn't expect was that this win was too painful for me to handle.

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My name is Ryan Daut and I would love to have you as a follower. Click here to go to my profile page, then click FOLLOW in the upper right corner if you would like to see my blogs and articles regularly. My interests are poker, fantasy sports, mathematics, astrophysics, cryptocurrency, and computer gaming.

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