[3][4] O'Keefe began his career in 2008 with an internship at St George and Sutherland Shire Leader before moving to television in 2010 as a reporter for Ten News on the Gold Coast.
[10] Prior to being announced the permanent host of the 2GB afternoon drive program, O'Keefe had been a fill-in presenter on the show throughout 2022.
[9] In the lead-up to the 2023 Australian Indigenous Voice referendum, O'Keefe supported the Yes campaign, disagreeing with leading 2GB presenter Ben Fordham.
[12] As a police reporter for Nine News Queensland, O'Keefe was recognised by the Gold Coast Media Club in 2014 for his story on the Broadbeach Bikie Brawl in October 2013.
[13] O'Keefe received the Walkley Award for his work exposing gross negligence at Bankstown Hospital after a fatal mix-up resulted in nitrous oxide being administered to a newborn baby instead of oxygen.