Friedman won a World Series of Poker (WSOP) bracelet in 2003 in the $1,500 pot limit hold'em event earning him $109,400. Later, at the WSOP circuit event at Harrah's Rincon in 2005, he won the second place prize of $363,165. At the 2006 WSOP Main Event, Friedman outlasted over 8,700 other players, finishing 20th and securing $494,797. During the tournament, Friedman was noted for an incident with Jeff Lisandro, in which Friedman felt that Lisandro had not put in his ante, worth 5,000 chips, in a hand. Friedman and Lisandro argued constantly through the hand, with the dealer telling them both to stop bringing it up. Friedman would not stop and implied that Lisandro "robbed" the other man of the 5,000. Lisandro was very upset to hear that, and argued with Friedman, telling him he would "take your head off, buddy". Friedman tried to settle things with Lisandro afterward during play, but Lisandro refused to talk to him. Many in the poker world criticized Friedman for his actions, including Norman Chad of ESPN and Todd Brunson of Cardplayer Magazine. In the end, it was discovered in the replay that Lisandro did in fact put in the ante. (In posting one of the blinds, a third player at the table forgot to put in his ante; the dealer corrected his mistake.)