Casino Trivia

In his first starring role since ‘Good Will Hunting’ in 1997, Matt Damon headed a gifted cast as gifted poker player Mike McDermott in the cult classic ‘Rounders’ – described by Elvis Mitchell, film critic at ‘The New York Times’, as ‘mischievously entertaining’ – in 1998. In so doing, he played a part in the poker ‘boom’ of the early- to mid-Noughties, insofar as several poker superstars, including Chris Moneymaker, who the World Series of Poker (WSOP) Main Event in 2013 as an online qualifier, cite ‘Rounders’ as the inspiration for their early interest in the game.

Damon reportedly spent $25,000 on ‘researching’ his role in ‘Rounders’ and has since enjoyed playing in various poker tournaments, although with little financial success. Indeed, his live earnings amount to just $540, which he collected for finishing forty-fifth in the World Poker Tour (WPT) $250 No Limit Hold’em – Deepstack Bounty event at Foxwoods Resort and Casino in 2011. Described by ‘Poker Princess’ Molly Bloom as ‘modest’, ‘down-to-earth’ and ‘gracious’, Damon reportedly turned up just once for the exclusive, high-stakes poker games for which she was indicted in 2014.

Damon was criticised for his ‘acting’ in the 2009 WSOP Ante Up For Africa event in which, having made a speculative call with 10-6 offsuit from the small blind, he flopped a full house. After an initial tell-tale ‘jolt’, Damon tried to feign disinterest in the board and the action and, when opponent Scott Wilson, on a pair, bet $6,400 on the turn, seemingly agonised over the call. Rather than ‘pulling the trigger’, Damon checked again on the river but, unimpressed, Wilson simply checked, leaving the Hollywood star shaking his head at his missed opportunity.

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.

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 888.com 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 388^th 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.