Rubuta ci gaba ga wannan sakin layi - Simon ya kasance mai wasan poker na yau da kullum, da kuma Texas Hold 'em musamman. An gabatar da shi ga wasan tun yana yaro ta hanyar wasannin karta na iyali na mako-mako da tafiye-tafiye na gidan caca tare da kakansa. Simon bai dauki kansa a matsayin dan wasa mai mahimmanci ba har zuwa wasan a gidan marubucin David Steinberg tare da 'yan wasan "masana", wanda ya karfafa shi ya yi nazarin wasan kuma ya shiga wasanni da yawa, kodayake ya yanke shawarar kada ya zama kwararre. Ya yi gasa a Wasannin Wasannin Wasanni na Duniya (WSOP) a kowace shekara tsakanin 2007 da 2011, yana gamawa a cikin kuɗi a cikin abubuwan da suka faru shida. A shekara ta 2007, a cikin 'yan wasa 6,358 $ 10,000 No-Limit Texas Hold'em Main Event, ya gama na 329 tare da $ 39,445. Ya kuma gama 16th lashe $ 35,493 a $ 1,000 1,048-player No-Limit Hold'em w / Re-Buys a 2007, 41st lashe $ 10,708 a $ 1,000 706-player No-Limit Hold'em w / ReBuys a 2008, 53rd lashe $ 10,692 a $ 1,000 879-player No-Limit Hold'em w / ReBuys a 2008, 20th lashe $ 24,066 a $ 10,000 275-player World Championship Pot-Limit Hold'em a 2009, da kuma 500th lashe $ 23,876 a $ 10,000 6,865-player No-Limit Hold'em Championship a 2011
Ka yi haƙuri. Ya kuma lashe $ 300 438 mai kunnawa Ba-Limit Hold'em Bounty $ 100,000 Guarantee a 2009 L.A. Poker Open, ya lashe $ 22,228. Babban nasarar da ya samu dangane da girman filin da kyautar kudi ita ce $ 200 1,082-player No-Limit Hold'em $ 150,000 Guarantee a 2010 Winnin O 'The Green, inda ya lashe $ 57,308. Wasannin wasannin sirri na Simon tsakanin sa da abokansa sanannun an bayyana su a matsayin "rashin hankali da nishaɗi sosai". Sunan su ya jagoranci Playboy TV don samar da wasan kwaikwayon "Sam's Game", sigar talabijin da ke nuna Simon a matsayin mai watsa shiri da kuma masanin bukukuwa na wasan Texas Hold 'em na Las Vegas; ya samar da wasan kwaikwayon. A baya ya bayyana a wani labarin 2009 na "High Stakes Poker".