At 28 years old, New Milford, Connecticut native Jackson Olson has gone from chasing the traditional baseball dream to becoming one of the most recognizable faces of the Savannah Bananas — and now he’s trading Banana Ball for the ballroom on Season 35 of ‘Dancing with the Stars.’ Jackson joins us to talk about how he landed a spot on the Bananas, finding his personality as a performer in his early 20s, and the team’s mission to inject fun back into baseball. He breaks down how Banana Ball actually works, the social media machine behind the team, founders Jesse and Emily Cole’s PT Barnum-inspired approach to entertainment, his lingering MLB ambitions, and what he makes of critics — including Dave Portnoy — who think the Bananas are ruining baseball.
Then it’s time to dance. Jackson talks about partnering with Emma Slater on ‘Dancing with the Stars,’ training for five hours a day until his feet were shredded, and why learning to dance has been one of the hardest things he’s ever done. He also opens up about dealing with anxiety, using box breathing to cope, meeting Derek Hough, and setting his sights on the Mirrorball Trophy. Plus, we get into kids dressing up as him for Halloween, John Cena and Kristen Bell, his love of Hugh Jackman and ‘The Greatest Showman,’ becoming a very late musical-theater convert, his relationship with Maggie Sajak, why he wants kids watching him to feel free to show a little more personality, and so much more.
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