Olesker attended the University of Maryland where he was on the staff of the school newspaper, The Diamondback, serving as the sports page editor.
He was also a commentator on WJZ-TV from 1983 through December 2002, and his columns were syndicated in other newspapers such as Newsday and the Pittsburgh Post-Gazette.
[2][3] Olesker resigned from the Sun on January 4, 2006, after it was alleged that his columns contained passages plagiarized from articles at other newspapers.
[6] The Maryland Lieutenant Governor Michael Steele also accused Olesker of making up quotes.
[8][9] Olesker is the author of Journeys to the Heart of Baltimore (Johns Hopkins University Press, 2001, ISBN 9780801867545) and co-authored Leap into Darkness, a 1998 memoir of a Holocaust survivor.