Andrew Bassano Brewer returns for his 5th appearance with JBK On Air for more predictions about American politics, economic outlook and President of the United States Donald J. Trump's madness. He believes the upcoming midterm elections in the United States will bring a blue tsunami, rendering Trump into a lame duck with two years left in his second term. He forecasts impending economic issues in the United States citing fractured relationships with longstanding trading partners and ongoing instability of the US dollar. Andrew and Jimmy worry about climate change with it being the warmest October in recent memory. Andrew also discusses his extensive collection of Magic 8 balls & his love for Halloween in this new episode! Rate, review & subscribe for new episodes!

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Comedian & entrepreneur Ambur James returns to JBK On Air for the second time to share her comedic writing process, her strangest gig & much more. Ambur and JBK debate if men or women lie more in relationships, the biggest red flags to avoid, & her qualifications for a romantic partner. Finally, Ambur uses the JBK On Air bump to manifest her aspirations of being on a sitcom in the future.

Grammy nominated jazz musician and composer Steve Allee joins the program for his first appearance since EP3 on June 10, 2020. Jimmy catches up with Steve through the JBK On Air Questionnaire revealing he’d be starstruck by Herbie Hancock & much more!

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Sara Press is a reality TV show producer and podcaster based in Chicago, IL. Sara joins JBK On Air to discuss her career working on shows like The Celebrity Apprentice, her experiences with the 45th & 47th POTUS Donald J. Trump & much more! Check out Sara's work on her podcast Nothing Small About Business & follow @withsarapress on Instagram! Links to watch, rate, review, subscribe available now at https://linktr.ee/jbkonair

“Press Box Chronicles” New York Times best selling author Jeff Pearlman joins JBK On Air to discuss his career in writing for Sports Illustrated and his latest book Only God Can Judge Me: The Many Lives of Tupac Shakur released in 2025. Jeff also discusses his book Football for a Buck: The Crazy Rise and Crazier Demise of the USFL to show POTUS Donald J. Trump is a true conman as the current Commander-in-Chief. Jeff also is bold enough to take the JBK On Air Questionnaire revealing his favorite smell and if he prefers window or aisle. Follow Jeff & see his work on TikTok @jeffpearlmanauthor for more! New episode is available now wherever you get podcasts! #jbkonair

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Greg Olear returns for his third appearance with JBK On Air to promote his latest book Another Wonderful Secret: Infrequently Asked Questions About Jeffrey Epstein. The book gives people a better understanding of Jeffrey Epstein’s criminality and how it is connected to the daily chaos we see in 2026. Greg also rejoices in the New York Knicks making the NBA Finals for the first time since 1999, a rematch between the San Antonio Spurs.

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With loving memory of Bob Kevoian, we take a deep look into the JBK On Air vault with one of the proudest moments of my career both then and now.

I was fortunate enough to interview National Radio Hall of Fame member Bob Kevoian of The Bob & Tom Show for my morning show Casual Friday as a student at the University of Indianapolis. This was a dream come true for me to talk to a true legend in the radio business and someone who left his mark on Indianapolis as a cultural institution. I also had a personal connection with Bob who gave my father Chooch Kennedy a national platform to showcase his talent as a musician. Throughout my life Bob encouraged my broadcasting ambitions, providing kind words, equipment, as well as the time to talk to him on my show. He was larger than life, teaching me the importance of being in the moment and letting others shine is the true magic of radio as a medium. My heart is heavy and aches for everyone who misses him. But having recordings to look back on and smile through is what I choose to be grateful for now. Thank you for loving me Bob with your light, humor, and honesty. I am truly humbled and overjoyed to have been your friend!

- Jimmy

One of the most highly regarded psychics in the world Andrew Bassano Brewer returns to JBK On Air for his 4th appearance on the program. Andrew returns to reflect on the latest chaos from Trump 2.0, predicting ongoing economic issues in the coming months for the United States. Past episodes with Andrew can be found in the archives, anywhere that you get podcasts! Rate, review, like, comment & subscribe! Links for booking & more episodes - https://linktr.ee/jbkonair