Rob Sherwood Proves Staying in the Game is Key to Poker Success

Rob Sherwood has been following a path in tournament poker for more than 20 years that hasn’t put him directly into the spotlight very often. But his consistency and success across live and online poker allowed him to keep taking shots and traveling the world without much worry, waiting for his moments to come.

Before December, Sherwood had built himself a $1.1 million resume of results largely upon consistent five-figure results and the occasional standout moment – most notably making the Irish Poker Open Main Event final table in 2010.

Sherwood proved himself capable of maintaining that steady career on poker alone by keeping one key idea in mind: if you don’t play beyond your means and your bankroll, and you keep putting yourself in good spots, you’ll give yourself plenty of chances to break through.

Patience and consistency finally led Sherwood to the moment that finally changed his life in the way every poker player dreams of when they first start – a runner-up finish in the 2024 WPT World Championship, worth $2.2 million. Sherwood, 46, from Manchester, England, struck a steely and determined presence opposite the boisterous Scott Stewart and nearly pulled off the victory.

History tends not to remember so many of the runners-up in major events, and yet in Sherwood’s run to second and everything that led up to it there are lessons to be learned for anyone with aspirations towards a long and successful career.

It started for Sherwood, like for so many others, with card games at the kitchen table with his grandparents from the age of six, though it never felt so serious at that time. Sherwood pursued and secured a Mathematics degree from the University of Manchester, sought out and found space in the working world and after just a few years found himself in his 20s, made redundant in his job and in search of some meaning in his life.

Sherwood chose a path that a lot of people have sought out in their 20s, searching for meaning – he went out into the world in search of something intangible, and came back with everything he needed.

“It was kind of the standard backpacking route at the time for someone from the U.K.,” Sherwood recalled. “Southeast Asia – Thailand, Vietnam, Cambodia, and then Australia and New Zealand.” When he was in Thailand, one of the people who Sherwood crossed paths with introduced Texas Hold’em into the mix of card games they’d play late at night. There was a second half of a 1-2 punch later in Sherwood’s adventure that would seal the change in Sherwood’s life. “We were just playing card games, backpacking, just the usual sort of thing. Then, in Australia, I saw Late Night Poker. Started watching that, and I just got hooked.”

He had stumbled upon the revolutionary Late Night Poker, a show that predates both the World Poker Tour and World Series of Poker broadcasts with hole cards and helped explode the popularity of poker in the U.K. in the late 1990s and early 2000s. Upon his return home, Sherwood kept up with the TV show, bought some books and threw himself head-first into poker.

As someone who would remain conscientious and pragmatic throughout his poker career, Sherwood’s early days of taking poker seriously were also handled with care and consideration. But success quickly followed as he waded his way into the earliest days of an exploding online poker ecosystem.

“I came back and I worked a nine-to-five again, playing poker online in the evening,” said Sherwood. “Then my contract ended with that job, and I thought I’ll have one month off and then get another contract.

“And then I just never went back to work. I never planned to play poker full time – never on the card – but I was just making good money. Online poker was so easy back then.”

Online poker unlocked a lot of opportunities for Sherwood in those early days, including his first major TV exposure in tournament poker, when he qualified to participate in MansionPoker’s Poker Dome Challenge in Las Vegas in late 2006.

Players from the United States, Canada and Europe converged to play in one of 36 televised single table tournaments on a Poker Dome Challenge broadcast that was well ahead of its time. Players had a 15-second shot clock and were completely sequestered from the crowd and all electronic devices in a glass-encased set located just off of Fremont Street in Downtown Las Vegas.

Sherwood, just a few years into his professional career, won his preliminary match and semifinal to lock up $75,000 in earnings and a spot in the final. 

“It was pretty fast, pretty turbo, but there were players in there from freerolls,” Sherwood recalled. “So there were some really inexperienced players. I was relatively experienced at that time, playing seriously for probably two years. I was on the Two Plus Two forums, reading as many poker books as I could get, using the very early poker software to sort of study.”

Sherwood settled for third place in the finale, missing out on the $1 million first-place prize but adding another $75,000 to his winnings for the trip for a total of $150,000.

He was one of many young 20-somethings of that era to enjoy a taste of money well beyond anything he’d enjoyed to that point, but Sherwood felt an immediate sense of responsibility that many of that demographic lacked at that time, especially with the unthinkable amounts of money floating around poker in the years immediately following the Moneymaker boom.

“I mean, a lot of players took it for granted,” said Sherwood. “There’s plenty of players I knew that were better players than me, that won loads of money and just wasted the money because they just assumed it was just going to be so easy to win forever. I was always a little bit more on the sensible side of money, which I think is just super important.

“The most important thing is to stay in the game.”

Sherwood displayed some staying power amongst the U.K. poker scene, continuing to post solid results both online and in occasional live events all over the world. His primary focus in poker turned to online heads-up Sit & Go tournaments for a time, with some online tournaments and qualifiers mixed in. Sherwood won his way into another major event in 2010, securing a discounted seat to the Irish Poker Open.

He returned to the broadcast airwaves and posted another strong showing on the way to a fourth-place finish, good for his €163,300 ($220,208) first-place prize and an additional €100,000 prize as the last PaddyPower online qualifier standing.

From that point on, Sherwood enjoyed some 15 years of success in anonymity. He turned up to play the World Series of Poker most years, qualified for more events and traveled the world playing poker – posting results in 14 different countries on three continents.

But for all of his successes, the tournaments he satellite into and the occasional shots he took, Sherwood never went beyond his means. Entering the WPT World Championship at Wynn Las Vegas this past December, Sherwood had never so much as played a single $10K-plus buy-in event, outside of the WSOP Main Event.

Just like he had so many times prior in his career, Sherwood saw an opportunity to participate at a discount price by leaning into his expertise in satellites. It took a few tries, but on Sunday night, ahead of Day 1C, Sherwood locked up his spot. He showed up bright and early Monday morning, a little bit earlier than he normally would, and made that decision worth it.

“Staff in the satellite told us our chips will be in play from the very first hand at 11 a.m.,” said Sherwood. “The guy next to me said, ‘I’ll have a Grey Goose and Red Bull, please. And he was just smashing through the Grey Goose all day. He wasn’t bothered, and that kind of set the tone.”

Sherwood doubled his chips in the first few levels and managed to put chips in a bag – and then he repeated that feat for five straight days to secure a spot at the biggest final table of his career. Within 10 hands at that final table, three of the six players at that final table had been eliminated and each player had quickly locked themselves up over $1.5 million.

A deal was made to flatten the payouts, increasing that baseline to $2 million for third, and yet in what might seemingly project to be a more relaxed environment the chips continued to fly as Sherwood, Stewart and Eddie Pak buckled down for a knockdown battle for the title. Pak eventually bowed out in third, and thus Sherwood stared down Stewart with the title and the biggest amount of money either man had ever played for.

Sherwood sat as the perfect counterbalance and foil for Scott Stewart, leading to one of the most memorable and interesting heads-up battles in recent poker history. Alike in experience, and yet so completely different in approach.

“He’s just one of a kind. I couldn’t believe it when I was first on his table with three or four tables left, he was just sitting there, chatting away with his neighbors, sipping on his Budweiser like we were just playing some $100 nightly tournament. That’s part of his game, I think, to get himself feeling present and in the moment.

“I think if he tried to sit there quietly, very quietly like I do, I don’t think that would have worked for him. If I tried to act like him, chatting away and drinking, I wouldn’t be able to play my game either.”

In over 100 hands, both men had their opponents on the brink – Stewart to a chorus of cheers and reactions from his assembled crowd of friends, Sherwood quietly riding solo. The blinds got big, and the tournament slipped from between Sherwood’s fingers in the end. But in this experience, this $2.2 million win, Sherwood and Stewart shared the kind of moment that will shape the rest of their careers and their lives.

“We spoke in between hands,” Sherwood said. “We both wanted to win, and we’re both very different characters. But I felt like there was a lot of respect between us, and we were sort of saying to each other, ‘This is just 50/50, we’re gonna fight each other, and in the end, it’s gonna come down to one hand.’”

Stewart enjoyed the fanfare, the winner’s photos and the trophies, while Sherwood slipped quietly into the night. He’s done interviews and received plenty of congratulations from friends, family members and supporters, but beyond the disappointment of not securing the title it feels as though the runner-up finish will allow for Sherwood to maintain the same kind of workmanlike anonymity that he’s cultivated over two decades, whether intended or not.

This win will not thrust Sherwood into playing Triton Super High Rollers or WPT Alpha8 events. But it will lock down the things that have mattered the most in Sherwood’s pursuit of poker success.

“I’m not thinking, ‘Oh, look at all these material possessions I can buy with this money,’ said Sherwood. “I can relax now and not stress too much. In poker, what we’re trying to do, a lot of the time, is buy the freedom to live as we want.”