Jimmy DeCastro

Veteran broadcast executive Jimmy deCastro will step down from his post as Senior VP/Market Manager at Entercom Chicago.

“I’m officially retiring after my contract is up — but I’ve flunked retirement three times,” deCastro told Chicago media reporter Robert Feder. “I definitely have plans on doing something else in the gaming business, and I’m excited about that opportunity.”

He re-joined the radio ranks in 2017 as Entercom was acquiring CBS Radio, replacing Tim Pohlan. The colorful deCastro has a long and storied Chicago media history. He was president and GM of Tribune Broadcasting news/talk WGN (720), which he left in fall 2016 to launch After The Whistle, a sports marketing company and rep firm. But deCastro is best known for his work at legendary rocker “The Loop” WLUP-FM during its 80s heyday and for cofounding Evergreen Media in 1988. Along with partner Scott Ginsburg, deCastro helped transform Evergreen Media into AMFM, which grew to encompass 465 radio stations. In 2000 deCastro left AMFM and later became a consultant to America Online and president of AOL Interactive Services. In 2007 he launched national syndication firm The Content Factory, with sportscaster Dan Patrick among its multiplatform offerings.

“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,” Entercom COO Weezie Kramer said in an email to staff. “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.”

deCastro will continue to operate After The Whistle and plans to launch a new sports betting and gaming information venture through The Content Factory, Feder reports.