Jimmy de Castro Leaving Entercom Chicago
• Legendary Chicago media entrepreneur Jimmy de Castro announced he’s stepping down as SVP/Market Manager of Entercom’s properties in Chicago, Madison and Milwaukee, effective Dec. 13. “I’m officially retiring after my contract is up — but I’ve flunked retirement three times,” de Castro told Chicago media journalist Robert Feder, adding, “I definitely have plans on doing something else in the gaming business, and I’m excited about that opportunity.” A successor to de Castro is expected to be announced next week.
A staff memo from Weezie Kramer, Entercom Chief Operating Officer, read in part, “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.”
de Castro joined Entercom Chicago in Nov. 2017 after 3 1/2 years as President & GM of crosstown Tribune News-Talk WGN. “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 told Feder, adding, “I think [the group] is really set up for significant growth in the future.” Feder says de Castro will continue to operate After The Whistle LLC, a sports marketing and consulting company, with Entercom Chicago continuing among its clients. Through another one of his companies, The Content Factory, de Castro plans to launch a new venture involving sports betting and gaming information.
De Castro first rose to fame overseeing the legendary WLUP (The Loop)/Chicago in the ’80s, managing a high-wattage talent bench that included 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. de Castro co-founded Evergreen Media in 1988 with six stations; just over a decade later years Evergreen merged with Chancellor Broadcasting, creating a 465-station entity. That company later became AMFM, Inc., and de Castro served as Vice Chairman/CEO. He later served as Chairman/CEO of AMFMi, the company’s digital subsidiary. In 2000, de Castro founded Nothing But Net. Subsequently, he became a consultant to AOL and later served as President of AOL Interactive Services. In 2007, de Castro launched The Content Factory, an independent syndication company. His first big project was hiring ESPN vet Dan Patrick to launch a daily syndicated radio show, and the rest is history.
