Entercom/Chicago SVP/Market Manager de Castro to Retire

RADIO ONLINE | Friday, November 15, 2019

Jimmy de Castro

Entercom/Chicago Senior VP/Market Manager Jimmy de Castro is retiring following the expiration of his contract, effective December 13, reports Chicago media columnist Robert Feder. He'll continue to operate his sports marketing and consulting firm, After The Whistle, and plans to take his company, The Content Factory, into the sports betting and gaming information business. His retirement was revealed in an email to staff from COO Weezie Kramer. de Castro spent two years in the post for Entercom and oversaw the company's Chicago, Madison WI and Milwaukee clusters.

Kramer wrote, "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.

"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.

"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."

de Castro exited Tribune Media's crosstown WGN-AM/Chicago after three and a half years as President/General Manager in October, 2016 to focus on The Content Factory. de Castro is also the former Vice Chairman of the AMFM Radio Group (now iHeartMedia) and the former President of AOL Interactive.

de Castro began his career in marketing and sales, which eventually led to radio management and ownership. He co-founded six-station radio group Evergreen Media in 1988 and grew it into 465 stations within 12 years, creating AMFM Inc., the nation's largest radio broadcasting company at the time. de Castro served as Vice Chairman and CEO of the company and also served as Chairman and CEO of AMFMi, the company's Internet subsidiary.