Prominent Chicago media entrepreneur and radio powerhouse Jimmy deCastro has been tapped to run CBS Radio’s seven Chicago stations, soon to come under new ownership.
The unanticipated move was announced Monday by Entercom Communications, which is expected to close November 17 on its $1.7 billion acquisition of CBS Radio.
“As is often the case, mergers bring change and opportunity,” Weezie Kramer, chief operating officer of Entercom, told staffers in a memo. “New leadership can provide a fresh perspective and help accelerate performance. With that in mind, I hope that you are as thrilled as I am about the announcement of Jimmy de Castro as the new senior vice president and market manager of Entercom Chicago.
“Most of you know that Jimmy is no stranger to Chicago radio, and I hope that you will be excited about his infectious energy and comprehensive knowledge of the media landscape,” Kramer said.
In his new role, deCastro will oversee the top-billing all-news combo of WBBM AM 780 and WCFS FM 105.9, as well as sports/talk WSCR AM 670; Top 40 WBBM FM 96.3; adult album alternative WXRT FM 93.1; country WUSN FM 99.5, and classic hits WJMK FM 104.3.
DeCastro stepped down last fall after more than three years as president and general manager of Tribune Broadcasting news/talk WGN AM 720 to launch After The Whistle LLC, a sports marketing company and representation firm headquartered at 414 North Orleans Street in Chicago.
DeCastro will continue as CEO of After The Whistle in what was described as “a non-active management role.” His deal with Entercom calls for the company to serve as the Chicago station group’s digital media agency. “My brilliant partners at After The Whistle are going to help drive all of the digital messages for our terrific Chicago radio brands,” he said.
Effective with the Entercom takeover, he will replace Tim Pohlman, who held the job since January 2016. Under Pohlman, programming operations remained stable (including the multiyear renewal of Chicago Bears broadcast rights on WBBM Newsradio). But CBS Radio’s sales department was in constant upheaval, with Pohlman repeatedly shuffling his management team as revenues declined.
DeCastro rose to fame as impresario of WLUP FM 97.9 during the golden age of The Loop in the 1980s. He made a fortune transforming parent company Evergreen Media, which he co-founded in 1988, into AMFM, Inc., the nation’s largest radio owner at the time, encompassing 465 stations. In 2000 deCastro cashed out of AMFM (a forerunner of iHeartMedia) and later became a consultant to America Online and president of AOL Interactive Services.
In 2007 he created The Content Factory, a national syndication and new media company that propelled sportscaster Dan Patrick into multiplatform distribution. The Evanston-based company became the forerunner of After the Whistle.
“I am thrilled to join [president and CEO] David Field and Weezie Kramer as they take the helm of Entercom’s revered Chicago radio stations, leading them into a brave new era of broadcasting and content creation,” deCastro said in a statement.