Olesker resigned from the Sun on January 4, 2006, after it was alleged that his columns contained passages plagiarized from articles at other newspapers. Olesker is known for his liberal viewpoints and for his criticism of the administration of Maryland Governor Robert L. Ehrlich Jr. (R), whose press office in November 2004 issued an executive order banning state executive employees from talking with Olesker. The Sun unsuccessfully sued over the ban, in a case decided by the 4th U.S. Circuit Court of Appeals. The Maryland Lieutenant Governor Michael Steele also accused Olesker of making up quotes.
Olesker started writing for the Baltimore News American in 1978, prior to becoming a Baltimore Sun writer between 1979–2006. 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. After leaving the Baltimore Sun, Olesker was a columnist for the Baltimore Examiner until that newspaper ceased publication in 2009.
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. His other books include:
- Baltimore Sun Columnist Quits Amid Plagiarism Charges, FoxNews.com January 4, 2006.
- Kincaid, Cliff. "None Dare Call It Plagiarism". Accuracy in Media. Retrieved 22 June 2010.
- Court Favors Ehrlich on ban, Baltimore Sun, February 16, 2006
- Preston, Bryan. "Dead Even in Maryland". The National Review. Retrieved 22 June 2010.
- Associated Press (31 March 2005). "Balto. Newspaper Says Ehrlich's Ban Unconstitutional". Retrieved 22 June 2010.
- Dicarlo, Rachel. "The Governor vs. the Sun". The Weekly Standard. Retrieved 22 June 2010.
- Olesker, Michael (12 December 2001). "Life Support". The Pittsburgh Post-Gazette. Retrieved 22 June 2010.
- Olesker, Michael (26 March 2002). "Death Sends Daily Reminders at WTC Site". Newsday. Retrieved 22 June 2010.
- Olesker, Michael (1995). Michael Olesker's Baltimore: if you live here, you're home. Johns Hopkins Press. p. 5. ISBN 978-0-8018-5203-9.
- UPI (30 December 2007). "Sun TV Critic red inks 'The Wire' newsroom". UPI.com. Retrieved 22 June 2010.