Tom Dwan Loses Big to Phil Hellmuth: "I Felt Really Dumb."

Unless you’ve been living in a cave these last thirty years, you’ll know Phil Hellmuth as one of the titans of poker since his maiden WSOP Main Event win in 1989 at the age of just 21 years old. The Poker Brat is 54 now, and he stars in this latest Throwback Hand of Poker After Dark action against a man who, at the time of filming, was virtually half his age. Tom Dwan, the pin-up boy for the online aggro generation, took on Hellmuth in yet another hand where all the chips were over the line.

It’s hard not to love Hellmuth in some way, even if you don’t like him, but everyone seemed to love Tom Dwan on his way up the ladder, including legions of online poker fans. In many senses, Hellmuth and Dwan sitting down in a hand against each other is the universal match-up that illustrates that anyone can win poker in their own style. Phil Hellmuth’s white-magic-based early career matured into a dogged determination to keep showing up in ranking tournaments, particularly the World Series of Poker, in which he holds the record of having won fifteen bracelets.

Tom Dwan mutated from an aggressive online grinder who shot his way up the levels to a high stakes cash game legend who embraced new variants. While Hellmuth has mostly stuck to No Limit Hold’em, Dwan has recently become the poster player for the Short Deck Poker generation. Fast action was always Dwan and consistency at the highest level was more Hellmuth. It amuses me in this episode of Poker After Dark that they flip roles a little in the playing-out of the hand. When to rush and when to slow it down for value is a distinction that is heavily reliant on each additional community card. But when you have six players around the table with these guys experience, the margins for error are practically non-existent.

If two generations of poker player going head-to-head is fun, then, trust me, witnessing three is one of the poker railbird’s biggest guilty pleasures. There’s no better place to watch this happen that in Las Vegas, home of the World Series of Poker Main Event. It’s not that the WSOP Main Event doesn’t have the best players from all over the world competing in No Limit Hold’em for one of the biggest prizes in the game. It does. But what the WSOP always has, seemingly at every table if you’re huddled into your hoodie in the Rio, is some of the worst, too.

Check out more from Tom Dwan right here as he goes up against Antonio Esfandiari. Want to see more on-demand footage? The Return of Tom Dwan on Poker After Dark was as epic as it sounds, and the three nights of action are right here.

In 2017, the World Series of Poker was my focus for a fortnight of reporting which barely stopped. Each day was 12 hours of wall-to-wall interviews, discussions and articles. So, on my only day off, where did I head? Did I climb Red Rock? Did I dine out in some of the finest restaurants on planet Earth? Did I cruise the Strip in search of neon-lit entertainment? You’ve probably guessed exactly where I spent my time. At the tables myself, right back in the cool-box frozen air of the Rio.

I didn’t fancy blowing my entire earnings during the series, so I decided to warm up with a cheap tournament in the afternoon, which – like every tournament during World Series – had hundreds of runners. It was fun to be the sole Brit at the table and being a writer, I’m more of a listener than I am a talker. I enjoyed watching some of the players at my starting table battling. Two of them were at opposite ends of the playing spectrum. The eldest of my opponents was a cash game player from Chicago, who told me at length about the club he came from. He was hugely proud of it. According to him, if you could run a profit where he came from (ad he did) then you could run a profit anywhere. To be fair to him, I thought he was the best player at my table, and I loved watching him play. Whatever amount of chips I considered to be the most awkward to be bet, he’d wager it, always putting his opponent into an area of self-doubt. I stayed out of his way, but one player who didn’t was at the other end of the age gap.

Playing poker players who are 21 and covered in tattoos can be an intimidating experience for newcomers. They do their best to look mean, they wear muscle-vests and baseball caps, they’re ventilated by several piercings. The New York Yankees fan who consistently re-raised our Chicago-based friend purely because of his age certainly played without visible fear. But as I discovered in a hand with them both, looks can be deceiving.

Risking your entire stack in a Poker After Dark episode isn’t common, even if Dwan and Hellmuth do it in this classic Throwback hand. But in the chiller cabinet of a $150-entry Rio Daily, it’s happening every other hand at every single table. Having re-raised the Chicago retiree – our elderly player having revealed he owned a chain of self-storage units that printed money faster than he could bet it – the New Yorker found himself ahead of the chip average. But every hand he wasn’t involved in, the Windy City wizard did the same thing. I could see, like every other player at the table – that it was only a matter of time before the two of them clashed for the lot.

When it came, I escalated the action, four-betting over the top of the Yankees fan with Ace-Queen, Doyle Brunson’s least favorite hand for a reason. I was five-bet by Chicago, and when New York went Billy Big Apples, raising all-in for over fifty big blinds, I side-stepped what I assumed would be a bloodbath. I was right for once. Chicago moved all-in with Ace-King and he was up against the Yankees youngster’s pocket queens. I was the middle generation and found myself on the periphery. I didn’t mention that either of them had one less out because of my folded hand. A king landed on the flop and Chicago had eliminated his East Coast adversary, building a dominant stack against the rest of the table.

Just as Tom Dwan and Phil Hellmuth prove in this latest Throwback Hand, bridging the generation gap can be more about meeting in the middle than anything else. Squeezing out the middle man – in their case Phil Ivey – helps a bit, too.

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