His first poker title came in 2012, when he won a side event at the PokerStars Caribbean Adventure for $116,230. In March 2013 he won the WSOP Circuit event in Atlantic City, New Jersey, earning $174,147. That year he cashed in the WSOP Main Event for the first time, finishing in 489th place. Prior to the 2015 Main Event, McKeehen's largest cash came for a 2nd-place finish in the Monster Stack event at the 2014 World Series of Poker, where he earned $820,863.