After The Whistle | About the team
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About the team

Jimmy de Castro

Jimmy expanded his early career of selling radio sponsorships for the San Francisco Giants and 49ers into station ownership. He co-founded the six station radio group Evergreen Media, personally managing three of the stations in top ten markets, creating innovative brand campaigns and initiatives to accelerate their rise from last place to first in all key demographics.


Ten years later, he was Vice Chairman and a principle equity owner in AMFM, overseeing 465 radio stations, 64 million listeners, a nationwide marketing group, internet division, and cross platform network group.


His interest in the convergence of traditional media and the internet led him to eventually serving as president of AOL Interactive, where he was credited with launching one of AOL’s most successful products to a member base at the time of 33 million.


He subsequently launched his own content focused national syndication company, the Content Factory. He hired Dan Patrick from ESPN, and in just six weeks, Jimmy had signed over 80 stations for the Patrick show. By the time he sold it to Directv two years later, it was distributed to over 200 affiliates, on mobile, online, T.V., and publishing platforms.


At the request of Tribune Media president and good friend Larry Wert, he stepped away from his company to accept the position of president of WGN AM. The legendary 90 year old 50,000 watt station faced multiple challenges in recent years with declining revenues and morale. Jimmy restored staff momentum and returned the station to profitability, extending the rights of the Chicago Blackhawks through 2024, as well as the rights of Northwestern Football and Basketball.


Jimmy is known for his turnaround successes and creating strategic partnerships and innovative revenue streams. To him, possibilities are limitless, and he is excited about working with sports talents to help build their brand, financial security, and subsequent After The Whistle plans.