Nyora kupfuurira kweiyi ndima - Simon akanga ari mutambi wenguva dzose wepoker, uye Texas hold'em zvikurukuru. Akasvitswa kumutambo uyu achiri mwana kuburikidza nemitambo yepoker yemhuri yevhiki nevhiki uye nzendo dzekasino nasekuru vake. Simon haana kuzviona semutambi akakomba kusvika pamutambo kumba kwemunyori David Steinberg nevatambi vanoverengeka "vakadzidza", izvo zvakamukurudzira kudzidza mutambo uye kupinda mumakwikwi mazhinji, kunyangwe akafunga kusave nyanzvi. Akakwikwidza kuWorld Series of Poker (WSOP) gore rega rega pakati pa2007 na2011, achipedzisa mari mumitambo mitanhatu. Muna 2007, pavatambi 6,358 $ 10,000 No-Limit Texas Hold'em Main Event, akapedza 329th ne $ 39,445. Akapedzawo 16th kuhwina $ 35,493 pa $ 1,000 1,048-player No-Limit Hold'em w / Re-Buys muna 2007, 41st kuhwina $ 10,708 pa $ 1,000 706-player No-Limit Hold'em w / ReBuys muna 2008, 53rd kuhwina $ 10,692 pa $ 1,000 879-player No-Limit Hold'em w / ReBuys muna 2008, 20th kuhwina $ 24,066 pa $ 10,000 275-player World Championship Pot-Limit Hold'em muna 2009, uye 500th kuhwina $ 23,876 pa $ 10,000 6,865-player No-Limit Hold'em Championship muna 2011
. Akakundawo $300 438-mutambi No-Limit Hold'em Bounty $100,000 Guarantee pa2009 L.A. Poker Open, achikunda $22 228. Kukunda kwake kukuru maererano nehuwandu hwemunda uye mubairo wemari yaive $ 200 1,082-mutambi No-Limit Hold'em $ 150,000 Guarantee pa2010 Winnin O 'The Green, kwaakakunda $ 57,308. Mitambo yaSimon yepachivande yepoker pakati pake neshamwari dzake dzine mukurumbira yakatsanangurwa se"inotyisa uye inonakidza zvikuru". Mukurumbira wavo wakatungamirira Playboy TV kubudisa chiratidziro "Mutambo waSam", shanduro yeterevhizheni inoratidza Simon semubati uye tenzi wemitambo yemutambo weLas Vegas mukurumbira weTexas Hold 'em; akabudisa chiratidziro. Akanga ambobuda pane imwe nyaya ya2009 ye"High Stakes Poker".