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‘Gamblers,’ Episode 5: The Poker Player Who Couldn’t Be Solved

Phil Galfond once turned a single $100 deposit into millions on a poker site. But to prove he was the best, he issued a challenge and dug a hole that would require a miracle to overcome.

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Gamblers is a podcast about men and women who live by their wits and wagers. People who bet big on themselves, and won. From a road-hustling pool shark to a punk-rock horse handicapper to a sports bettor who could move lines, the six-part anthology series focuses on the fascinating lives of professional underground gamblers and how they make their money.

This is the story of a miracle, and the story of the poker player who performed it. It’s the story of a college dropout who used a single $100 deposit on an online poker site to win millions and millions of dollars. The story of a man who mastered poker, then taught his secrets to hundreds of younger players, only to watch those students leave him in their dust and reinvent the game in the process. And it’s the story of a man who came back from retirement, relearned the game he once mastered, and gave himself one last shot to reach the top—a shot that would require a miracle.

Phil Galfond’s life had changed dramatically. Even though he was building a poker business, he wasn’t playing much poker at all. He had transitioned from poker pro to poker coach to now expanding his company Run It Once into a real money poker site. He wasn’t a gambler anymore. He was a businessman. And he was fine with that. But something still gnawed at him.

“I noticed that my training video views had been going down and started to think, ‘Oh I guess that makes sense because I haven’t really been playing much and people are probably interested in learning from people that they see actively playing at the tables,’” Phil says.

Phil had made the decision to hang up his guns all on his own just a decade into his career. He didn’t get felted and go broke. He started a business and a family. When he was playing, he was good. Maybe even the best. Did anyone remember? Did any of these new poker whiz kids know about Phil Galfond? But more than all that, what really ate away at Phil was wondering whether or not he could still play. Could he do what he had done so many times before, and build his bankroll and his skills up—piece by piece?

He couldn’t shake the feeling, so he did something about it. In November of 2019 he issued a public challenge: He would lay a three-to-one side bet to any poker coach who could play him heads up at high-stakes pot limit Omaha for 25,000 hands and come out ahead.

“This is the golden child who dominated and then left the game for a while,” says David Tuchman, host of the Under the Gun poker podcast and World Series of Poker commentator for ESPN. “To me, it was a great comeback story. We heard about his wife playing poker more than we heard about him playing. He was off running a business, and he was a dad, and had so many other things. Then every summer, we would see him play a handful of events at the World Series. But this was the golden child coming back to see if he could do it, to see if he still had it.”

But Phil wasn’t even sure if he still had it. He had wondered himself whether he was rusty. He had a lot of catching up to do, so he got some active players to teach him how to use “solvers,” which are powerful computer programs that can simulate so many decisions in a poker hand that it can tell you the correct “game theory optimal” or GTO strategy to play. When Phil started playing poker online in 2003, solvers didn’t exist. Once top players were able to program computers to find these optimal plays, it took their games to new levels. But it required a serious amount of time and study.

“So now there’s a tool telling me the right way to play hands, but I need to figure out why because I can’t possibly memorize how to play every hand perfectly,” Phil says. “I need to understand the concepts behind it so that I can apply those to any situation that comes up. And the more I studied, the more I felt excited because I felt my skill set still was important and still was valuable in the modern era of poker.”

Phil’s first challenge was against a European high-stakes PLO player who went by the name of VeniVidi1993. He preferred to keep his true identity a secret, and to this day his real name is still widely unknown.

The match would be 25,000 hands of 100/200 PLO, with Phil putting up €200,000 and Veni putting up €100,000. Whoever finished ahead after 25,000 hands, even if they were only up a single euro, would keep whatever they won during the match, plus the side bet. I asked Joey Ingram, a popular podcast host and an ambassador of what he likes to call “the great game of pot-limit Omaha,” who he thought the people in the poker world were making the favorite between Phil and this anonymous European player.

“I don’t know, it’s a good question,” Ingram responded. “I don’t think people knew what to expect because they didn’t really know VeniVidi. They were wondering why Phil would challenge one of the perceived top guys right away. There was a lot of chatter on social media. I’m pretty sure a lot of people made big side bets. It seemed like there was a pretty good amount of money that was getting bet on the challenge.”

The players had agreed to play five days a week, a minimum of four hours a day on two tables simultaneously. That was usually enough to play about five or six hundred hands in a day. At that rate, with days off, they would play 25,000 hands in about four or five months, and all of it was broadcast live on Twitch.

“The fact that it was on a big stage, it was a lot more intense and draining than I thought it was going to be,” Phil says. “And it was less fun than I thought it was going to be.”

As the match started, Phil had some small losses, but he still felt pretty good about how he was playing.

“For the first few sessions, I felt great, even though I was losing,” Phil recalls.

The losses started to pile up on Phil. Session after session he lost. Now some of this was to be expected. PLO is a game with big swings.

But after 7,000 hands, Phil was stuck €700,000, or nearly $800,000. That’s more than three times the side bet he had with VeniVidi. That’s seven times what Phil was putting up. And there were still nearly 20,000 hands left to play.

“At some point you have to think, ‘Well, maybe he knows something I don’t or maybe just I’m wrong. I’m out of practice,’” says Phil. “Money aside, just losing at a game again and again is really not fun, it’s really depressing. And this kind of just felt like getting beaten over the head day in, day out.”

Around the 7,500th hand, Phil finally had a winning session. He won €80,000.

“And then the very next session, I had my biggest loss, which was something like €280,000 or €260,000,” Phil says. “So I went from having my biggest win, which was only €80,000, to my biggest loss, which was over three times that.”

David Tuchman was doing on-air commentary during the session.

“It was akin to watching a bloody UFC fight, the kind of UFC fight where you really don’t want to watch anymore,” Tuchman recalls. “I mean, we watch UFC because we love watching people get the shit kicked out of them, right? But when it gets really ugly and somebody really starts to get hurt, that’s when it almost becomes uncomfortable for us to watch.”

So in case you’re keeping score, after about 10,000 hands, Phil was down €900,000 to Venividi. An ungodly amount. Before, Phil thought that he was risking €200,000 on a match that might end with one of them up or down maybe less than €100,000. But now he was looking at losing €200,000, plus the €900,000 he had already lost, plus whatever else he might lose over the next 15,000 hands. If these results kept up, it could be ruinous.

To hear the full Phil Galfond episode, click here, and be sure to follow on Spotify and check back every Wednesday for new Gamblers episodes. This excerpt has been lightly edited for clarity and length.