He hosts the ESPN Baseball Tonight daily podcast and is one of about 575 voters for the Baseball Hall of Fame. Olney started out as a beat reporter for the Triple-A Nashville Sounds. He worked at the San Diego Union-Tribune and the Baltimore Sun before winning an Associated Press award in his first year at The New York Times. Olney authored the book The Last Night of the Yankee Dynasty which was published in 2004. He authored How Lucky You Can Be: The Story of Coach Don Meyer in 2010.