 In September of that year, O'Leary appeared as a celebrity judge in the 95th Miss America pageant.He is currently a member of ARHT Media's Board of Advisors, alongside Paul Anka and Carlos Slim.In January 2016, O'Leary offered to invest $1 million in the economy of Alberta in exchange for the resignation of Premier Rachel Notley and appeared with four other prospective leadership candidates at a conference for federal Conservatives in late February 2016 where he gave a presentation titled "If I Run, This is How."