Jackson Olson Talks ‘Dancing with the Stars,’ The Savannah Bananas, & ‘The Greatest Showman’

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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…