Sii wad inaad u qorto faqradahan-- Simon wuxuu ahaa ciyaaryahan caadi ah oo ku ciyaara turubka, gaar ahaan Texas Hold'em. Waxaa lagu soo bandhigay ciyaarta isagoo ilmo ah iyada oo loo marayo ciyaaraha turubka toddobaadlaha ah ee qoyska iyo safarada khamaarka ee awowgiis. Simon ma uusan tixgelin inuu yahay ciyaaryahan dhab ah ilaa ciyaar ka dhacday guriga qoraaga David Steinberg oo ay la ciyaareen dhowr ciyaartoy "aqoonyahan", taas oo ku dhiirrigelisay inuu barto ciyaarta oo uu galo tartamo badan, in kasta oo uu go'aansaday inuusan xirfadle noqon. Wuxuu ka qeyb galay tartanka World Series of Poker (WSOP) sanad walba intii u dhaxeysay 2007 iyo 2011, isagoo ku guuleystay lacag lix dhacdo. Sanadkii 2007, 6,358-ciyaaryahan $10,000 No-Limit Texas Hold'em Main Event, wuxuu dhammeeyay 329aad oo leh $ 39,445. Waxa kale oo uu ku soo dhamaaday 16-aad isagoo ku guuleystay $ 35,493 $ 1,000 1,048-ciyaaryahan No-Limit Hold'em w / Re-Buys sanadkii 2007, 41-aad oo ku guuleystay $ 10,708 $ 1,000 706-ciyaaryahan No-Limit Hold'em w / ReBuys sanadkii 2008, 53-aad oo ku guuleystay $ 10,692 $ 1,000 879-ciyaaryahan No-Limit Hold'em w / ReBuys sanadkii 2008, 20-aad oo ku guuleystay $ 24,066 $ 10,000 275-ciyaaryahan World Championship Pot-Limit Hold'em sanadkii 2009, iyo 500-aad oo ku guuleystay $ 23,876 $ 10,000 6,865-ciyaaryahan No-Limit Hold'em Championship sanadkii 2011
Waxaad Waxa kale oo uu ku guuleystay $300 438-ciyaaryahan No-Limit Hold'em Bounty $100,000 Guarantee ee 2009 L.A. Poker Open, isagoo ku guuleystay $ 22,228. Guushiisii ugu weyneyd ee la xiriirta baaxadda garoonka iyo abaalmarinta lacageed labadaba waxay ahayd $ 200 1,082-ciyaaryahan No-Limit Hold'em $ 150,000 Guarantee ee 2010 Winnin O' The Green, halkaas oo uu ku guuleystay $ 57,308. Ciyaaraha gaarka ah ee Simon ee ka dhexeeya isaga iyo saaxiibbadiisa caanka ah waxaa lagu sifeeyay inay yihiin "kuwa adag oo aad u madadaalo badan". Magacooda ayaa u horseeday Playboy TV inay soo saarto barnaamijka "Sam's Game", oo ah nooc telefishan ah oo ay ku jiraan Simon oo ah martigeliyaha iyo maamule xafladaha ciyaarta caanka ah ee Las Vegas Texas Hold 'em; wuxuu soo saaray bandhigga. Wuxuu horey uga soo muuqday 2009 dhacdo ka mid ah "High Stakes Poker".