Kevin Pollak

California-born actor, comedian and impressionist Kevin Pollak is famous for his roles as Lieutenant Sam Weinberg in ‘A Few Good Men’, Todd Hockney in ‘The Usual Suspects’ and Philip Green in ‘Casino’, among others. However, in the world of poker, Pollak is best known for his deep run at the World Series of Poker (WSOP) Main Event in 2012 – his first ever appearance in the WSOP – when he exceeded even his own expectations by finishing 134th of 6,598 entrants and collecting $52,718 in prize money.

Indeed, the 2012 WSOP Main Event was also memorable for the bad beat Pollak suffered at the hands of Kirill Rabstov on day five of the tournament; both players went all-in pre-flop with pocket queens, but Rabstov hit a backdoor flush draw on the flop and hit his suit on the turn and the river, while Pollak watched, helplessly, hands on head. Far from discouraged, Pollak has since played regularly in the WSOP Main Event and, although he has yet to better his 2012 finish, in 2019 he broke off filming ‘The Marvelous [sic] Mrs. Maisel’ in Brooklyn, New York and took his seat at the Rio All-Suite Hotel & Casino in Las Vegas straight from the airport.

A lifelong poker player – or, at least, since the age of 10 or 11 – Pollak started playing more seriously at the Mirage and the Riviera in Las Vegas during filming of ‘Casino’ in 1994. He still plays, weekly, in a Hollywood home game that he has been running since 2010, in some smaller buy-in events in Los Angeles and in charity events.

Teddy Sheringham

Retired striker Edward ‘Teddy’ Sheringham enjoyed an illustrious career with six different football clubs, including Tottenham Hotspur and Manchester United, and with the English national team. However, some years before he finally retired as a player in 2008, at the age of 42, Sheringham had started playing live tournament poker. He made his debut in that sphere on home soil in 2005, finishing second at the Fahrenheit Festival in Southend-on-Sea, Essex and third in the Pacific Poker Open in Maidstone, Kent, for cashes of $7,230 and $20,000, respectively.

Other major cashes over the years have also included $66,738 for a fourteenth-place finish in the World Series of Poker Europe (WSOPE) Main Event at the Empire Casino in London in 2009 and $28,530 for finishing 388th in the World Series of Poker (WSOP) Main Event at the Rio All-Suite Hotel & Casino in Las Vegas in 2012. However, Sheringham enjoyed his biggest payout, so far, in between times; he reached the final table, which also included the likes of WSOP Main Event winner Martin Jacobson, in the the European Poker Tour (EPT) Main Event at Casino Vilamoura in Portugal in 2010, eventually finishing fifth and collecting $118,346.

All told, Sheringham has nearly $330,000 in live earnings to his name. He has been less active on the poker circuit in and around London, and elsewhere, in recent tears, but remains one of the few celebrities who have translated love of the game into real, tangible results against some of the best players in the world.

Jason Alexander

Actor and comedian Jason Alexander, born Jason Greenspan, is best known for his portrayal of the iconic George Constanza in the popular NBC situation comedy ‘Seinfeld’ in the Nineties. However, New Jersey-born Alexander is a passionate poker player and is, in fact, a veteran of the World Series of Poker (WSOP) Main Event, having made his first appearance at the Rio All-Suite Casino and Hotel in 2007.

He has yet to record a high finish at the WSOP Main Event but, by his own admission, plays competitive poker mainly ‘to have a great time’. Nevertheless, Alexander has nearly $30,000 in live earnings to his name, with his best live cash, nearly $17,000, coming in the WSOP $350 No Limit Hold’em event at Harrah’s Atlantic City Casino, in which he finished fifth of the 1,250 entrants, in 2010.

Alexander starting playing poker in college, but took more serious interest when televised celebrity poker became en vogue in the late Nineties and early Noughties. He freely admitted that a tutorial with 15-time World Series of Poker bracelet winner Phil ‘Poker Brat’ Hellmuth – with whom he shared a publicist at the time – ‘scared the living bejeezus’ out of him. Nevertheless, the tutelage eventually paid dividends, to the tune of $500,000 for his chosen charity, The United Way of America, when he launched a dramatic comeback won the final of ‘Celebrity Poker Showdown’, televised on the Bravo cable network, in 2006.

Michael Phelps

Maryland-born Michael Phelps, a.k.a. ‘The Baltimore Bullet’, is the most decorated Olympian of all time, with 28 medals, 23 of them gold, for long course swimming. However, Phelps was playing poker long before his retirement from competitive swimming following the 2016 Summer Olympics. In 2006, while living in Ann Arbor, Michigan, Phelps met professional poker player Jeff Gross at Casino Windsor, now Caesars Windsor, in Ontario, Canada and the pair subsequently room together for seven years in Baltimore, Maryland. Gross called Phelps ‘one of the best celebrity players around’.

Phelps actually achieved his best live cash, so far – a ninth-place finish, worth $5,213, in a World Series of Poker (WSOP) Caesars Palace Classic event in 2008 – before his retirement. Indeed, at the time of his retirement, it was speculated that he may play more frequently in live poker tournaments and may, indeed, sign a major sponsorship deal. So far, no sponsorship deal has been forthcoming but, in recent years, Phelps has finished in the money at a handful of smaller poker tournaments at various Las Vegas casinos, including The Venetian, Aria and Rio. All told, Phelps has just $9,873 to his name in live earnings but, most recently, finish fifth of 54 entrants in the $110 + 30 No Limit Hold’em – Nightly Event at the Aria Resort & Casino. Poker remains a hobby, rather than a career, for Phelps, but there is little doubt that he is a serious, talented player.

Tobey Maguire

California-born Tobias ‘Tobey’ Maguire is probably best known for playing Peter Parker, the alter-ego of Spiderman, in the Columbia Pictures trilogy between 2002 and 2007. However, according to Molly Bloom – dubbed the ‘Poker Princess’ by the press and indicted, in 2014, for running illicit, high-stakes poker games in Los Angeles and New York City – Maguire was the ‘best player’ of those that she encountered.

A regular player at the invitation-only poker games, which also featured Ben Affleck, Leonardo DiCaprio and Matt Damon, Maguire reputedly won in excess $30 million. However, over $300,000 of his winnings came from disgraced hedge fund manager Bradley Ruderman, who was later jailed for a fraudulent investment scam, known as a Ponzi scheme. Consequently, Ruderman was sued by his clients, as was Maguire, who settled out of court for $80,000, which was less than the amount the complainants were pursuing.

Between 2004 and 2007, Maguire achieved twelve cashes in live tournament poker, the best of which was $95,480 for winning the Phil Helmuth Invitational event during the National Championship of Poker at the Hollywood Park Casino in Inglewood, Los Angeles. All in all, he has lifetime live earnings of nearly $220,000 but, since 2007, has largely disappeared from the live poker scene and, so far, has showed no signs of returning, despite some unwanted attention in the Molly Boom memoir, ‘Molly’s Game’, in 2014 and the film of the same name – in which Maguire is not mentioned by name, but is rumoured to be the ‘Player X’ character, played by Michael Cera – in 2017.

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