Simon was a regular poker player, and Texas hold 'em in particular. He was introduced to the game as a child through weekly family poker games and casino trips with his grandfather. Simon did not consider himself a serious player until a game at writer David Steinberg's house with several "scholarly" players, which encouraged him to study the game and enter numerous tournaments, although he decided not to become professional. He competed at the World Series of Poker (WSOP) each year between 2007 and 2011, finishing in the money in six events. In 2007, at the 6,358-player $10,000 No-Limit Texas Hold'em Main Event, he finished 329th with $39,445. He also finished 16th winning $35,493 at the $1,000 1,048-player No-Limit Hold'em w/Re-Buys in 2007, 41st winning $10,708 at the $1,000 706-player No-Limit Hold'em w/ReBuys in 2008, 53rd winning $10,692 at the $1,000 879-player No-Limit Hold'em w/ReBuys in 2008, 20th winning $24,066 at the $10,000 275-player World Championship Pot-Limit Hold'em in 2009, and 500th winning $23,876 at the $10,000 6,865-player No-Limit Hold'em Championship in 2011. He also won the $300 438-player No-Limit Hold'em Bounty $100,000 Guarantee at the 2009 L.A. Poker Open, winning $22,228. His biggest win in terms of both field size and prize money was the $200 1,082-player No-Limit Hold'em $150,000 Guarantee at the 2010 Winnin O' The Green, where he won $57,308. Simon's private poker games between him and his celebrity friends have been described as "raucous and very entertaining". Their reputation led Playboy TV to produce the show "Sam's Game", a televised version featuring Simon as host and master of ceremonies of a Las Vegas celebrity Texas Hold 'em match; he produced the show. He had previously appeared on a 2009 episode of "High Stakes Poker".