Randy Michaels has been involved in large market radio broadcasting since the early 1970s, first in front of the mike as evening personality at adult contemporary WGR in Buffalo. He later moved into management, and was CEO of Jacor Communications in the 1990s selling to Clear Channel in 1999 and remaining there as CEO until 2002. Early in 2005, Michaels began working with Oak Hill Capital partners on acquisition opportunities, culminating in the creation of Local TV LLC, a company that acquired nine local network-affiliated television stations formerly owned by The New York Times Company. In early 2007, Michaels became CEO of the company. On December 22, 2007, Local TV announced it was acquiring eight large market stations from Rupert Murdoch's News Corporation.
On December 20, 2007 Michaels became executive vice president (EVP) of the Chicago-based Tribune Company and chief executive officer (CEO) of Interactive and Broadcasting operations as part of the management restructuring following the consummation of the Tribune Company privatization transaction.
 Under Mr. Michaels, The Tribune Co. was widely reported to have undergone a negative change in atmosphere, with instances of profanity from executives and strange memos being issued from management, as well as a controversial private poker party in the Tribune Towers. On October 23, 2010, Michaels was asked to resign as Tribune's CEO by the board of directors, and was replaced temporarily by a four-member Executive Council, and later by Eddy Hartenstein, member of the interim council and publisher of the Los Angeles Times
On October 14, 2011 Michaels was arrested for operating a vehicle while intoxicated in Middletown, OH.
- "Randy Michaels Named to NAB TV Board" (Press release). National Association of Broadcasters. 2008-04-07. Retrieved 2008-05-14.
- "About Us" (Web). localtvllc.com. Local TV LLC. August 2008. Archived from the original on 2008-06-25. Retrieved 2008-08-24. "We are currently in the process of acquiring a portfolio of 9 television stations. We intend to expand our media footprint, and are pleased to have the NYT stations as a foundation."
- "Press Room" (Press release). Local TV. 2008-08-22. Retrieved 2008-08-24. "Local TV LLC is a broadcast holding company created in 2007 to acquire nine heritage television stations in eight midsized markets. In 2008, the company acquired eight Fox Affiliates previously owned by News Corporation. Local TV is owned by Oak Hill Capital Partners, management and a consortium of bankers and high yield lenders...."
- "Oak Hill Capital Partners to Purchase Eight Television Stations From News Corporation" (Press release). Local TV. 2007-12-21. Retrieved 2007-12-22.
- "Tribune Completes Going-Private Transaction; Sam Zell Named Chairman & CEO". Tribune Company Press Room (Press release). Tribune Company. 2007-12-20. Retrieved 2008-08-24.
- Page Albiniak (2008-04-07). "Tribune Taps Clear Channel's Chase for Interactive Group". Broadcasting & Cable (broadcastingcable.com (Broadcasting & Cable)). Retrieved 2008-05-14.
- Feder, Robert (2 June 2010). "Poker party 'desecrates' Tribune Tower shrine". WBEZ. Retrieved 13 July 2011.
- Carr, David (18 October 2010). "Tribune Is Said to Seek Chief’s Resignation". The New York Times. Retrieved 13 July 2011.
- "Tribune Board Appoints Executive Council to Oversee Operations" (Press release). Tribune Company. 22 Oct 2010. Retrieved 2010-10-23.
- Szalai, Georg (6 May 2011). "Tribune Names Eddy Hartenstein President and CEO". The Hollywood Reporter. Retrieved 11 July 2011.
- Crain's New York Business. "101.9 kills the talk, cues the rock 'n' roll", July 17, 2012. After a yearlong experiment, Randy Michaels' Merlin Media pulled the plug on FM News 101.9 and started blaring alternative rock music once again.
- Kinsley, Michael. "My Most Productive Column Ever: Measuring Value by Word Count: What a Brilliant Idea!" The Washington Post, June 9, 2008. Accessed August 24, 2008. (Comments on Randy Michaels, with reference to article by Saba.)
- Saba, Jennifer. "Update: Tribune Hints at Big Staff and Page Cuts -- and Measuring Reporters' Value By the Inch". Editor & Publisher, June 6, 2008. (Subscription-only access.)