 In July 2010, O'Brien was the victim of a machete attack, which left him with serious injuries.In August 2019, he was named in Bermuda's squad for the Regional Finals of the 2018–19 ICC T20 World Cup Americas Qualifier tournament.In September 2019, he was named in Bermuda's squad for the 2019 ICC T20 World Cup Qualifier tournament in the United Arab Emirates.