Macdonald said his past gambling addiction had been initiated by a six-figure win at a craps table in Atlantic City. In an appearance on the "WTF with Marc Maron" podcast in 2011, Macdonald revealed that he lost all of his money gambling three times, and the largest amount he lost at once was $400,000. In the 2007 World Series of Poker, he came in 20th place out of 827 entrants in the $3,000 No Limit Texas Hold 'em event, winning $14,608. He made it to round two of the $5,000 World Championship of Heads-Up No-Limit Hold'em.