‘Game changer’ Jimmy de Castro retiring as Entercom Chicago boss

Jimmy de Castro

Legendary media entrepreneur 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.

“Jimmy was tasked with breathing new energy and positivity into the organization as we embarked on our journey as a new team. And Jimmy delivered,” Weezie Kramer, chief operating officer of Entercom, told staffers in an email. “His spark, creativity, experience, and business acumen were just what was needed to improve our brands, our culture, our business, and our building in Chicago.”

A successor is expected to be announced next week.

Entercom Communications

Since Entercom took over CBS Radio in 2017 de Castro has overseen the top-billing all-news combo of WBBM 780-AM and WCFS 105.9-FM, as well as sports/talk WSCR 670-AM; Top 40 WBBM 96.3-FM; adult album alternative WXRT 93.1-FM; country WUSN 99.5-FM, and classic hip hop WBMX 104.3-FM.

On his watch, Entercom slashed expenses, reduced its sales force by nearly one-third, and consolidated its studios and offices at Two Prudential Plaza from three floors to two. The company also signed a multiyear agreement to broadcast Chicago Bulls games on The Score and negotiated new union contracts with SAG-AFTRA and WGA.

Despite pushback from fans and critics, de Castro successfully overhauled programming on The Score — including the addition of David Haugh alongside Mike Mulligan in mornings and Dan McNeil alongside Danny Parkins in afternoons. He also unveiled a new format at 104.3 Jams and introduced new morning shows to B96 and US99 (the results of which are mixed so far).

“We did a lot of hard work and made some really tough decisions, but I’m very, very proud of what’s transpired in two years,” de Castro said. “I think [the group] is really set up for significant growth in the future.”

De Castro will continue to operate After The Whistle LLC, a sports marketing and consulting company headquartered in River North, with Entercom Chicago continuing among its clients. Through another one of his companies, The Content Factory, de Castro said he plans to launch a new venture involving sports betting and gaming information.

Before he last re-emerged from retirement, de Castro spent more than three years as president and general manager of news/talk WGN AM 720 under Tribune Broadcasting ownership.

De Castro first rose to fame as impresario of the former WLUP FM during the golden age of The Loop in the 1980s, where he managed Jonathon Brandmeier, Steve Dahl, Garry Meier and Kevin Matthews, among other stars. He’s also credited with bringing Erich Mancow Muller to Chicago 25 years ago this year.

De Castro made a fortune transforming 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 he cashed out of AMFM (a forerunner of iHeartMedia) and later became a consultant to America Online and president of AOL Interactive Services.

Here is the text of Kramer’s email:

I was thrilled beyond belief to discover that Jimmy de Castro was interested in returning to local radio as the new leader for Entercom Chicago post-merger just under two years ago. After all, Jimmy has always been known as a game changer in the industry and perhaps the one person who had the greatest impact ever on Chicago radio, so there was no one I would rather entrust with our iconic local brands, sports relationships, and talented team in Chicago than Jimmy.

The past two years have flown by and, as many of you already know, Jimmy has decided to retire from his leadership position overseeing Entercom Chicago, Madison, and Milwaukee and instead focus entirely on After the Whistle.

Jimmy was tasked with breathing new energy and positivity into the organization as we embarked on our journey as a new team. And Jimmy delivered. His spark, creativity, experience, and business acumen were just what was needed to improve our brands, our culture, our business, and our building in Chicago.

I am personally and professionally grateful for Jimmy and his many contributions to our team in Chicago and our business overall. No one can work a room like Jimmy. No one can make you smile like Jimmy. He is a people first leader and someone who made all of us better. He will be missed.

Graciously, Jimmy has agreed to stay in his role at Entercom past his contract deadline in order to help us transition to new market leadership. He will be around through mid-December, so all of you have plenty of time to say thank you! I know that all of you share in my appreciation for his leadership. As Jimmy might say, “Big Hugs” and thank you for everything.

Weezie