Chicago Radio: Jimmy de Castro To EXIT Entercom

Jimmy de Castro

Longtime Chicago  media executive Jimmy de Castro, who downsized and revitalized the seven Chicago radio stations owned by Entercom Communications, is ready to take a gamble on his next adventure.

“I’m officially retiring after my contract is up — but I’ve flunked retirement three times,” de Castro, 66, told me. “I definitely have plans on doing something else in the gaming business, and I’m excited about that opportunity.”

His last day as senior vice president and market manager of Entercom Chicago is expected to be be December 13.

As first reported by Robert Feder Friday, deCastro is retiring after a little over two years being appointed to the position.

A replacement will be named next week, reports TDog Media.

The longtime Chicago radio executive was installed as market manager for the former CBS Radio stations right after Entercom closed on its purchase of the radio group. Among the first moves he made was to flip 104.3 FM from WJMK’s classic hits format to a Classic Hip-Hop 104.3 Jams and adapting the legendary call letters identified with African-American Chicago radio, WBMX.

In addition to running WBMX, all-news WBBM-AM (and WCFS-FM), Top 40 outlet WBBM-FM (B96), country WUSN-FM (US 99), adult album alternative WXRT-FM and all-sports WSCR-AM (The Score,) DeCastro was also responsible for Entercom’s stations in Milwaukee and Madison, Wis.

His tenure was marked by cost cutting as well, including layoffs and reducing the number of floors Entercom had at Prudential Plaza from three floors to two.

DeCastro came into prominence in the early 1980s being hired at Heifel Broadcasting’s WLUP-FM (The Loop) as GM, at a time when Steve Dahl and Garry Meier were fired by the station for “assaulting community standards” (both returned to The Loop in 1986.) He became one of the investors in Evergreen Media, who purchased The Loop and WLUP-AM (now ESPN 1000) and became President of AMFM, the company formed by the merger of Evergreen Media and Chancellor, and was swallowed up by Clear Channel (now iHeartMedia) in 2000.

After serving as president of AOL Interactive and forming The Content Factory, DeCastro resurfaced as President and GM of WGN-AM and short-lived sports station WGWG-LP (The Game.)

Even though deCastro is retiring from radio, he isn’t entirely going away: he’s still President and CEO of his sports marketing company After The Whistle and plans to form a new sports gambling venture.