REVISITED: Jackson Olson — From Instacart to the Savannah Bananas

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About this episode

Before Jackson Olson stepped onto the Dancing with the Stars stage, he sat down with Rachel Uchitel to share the unlikely journey that brought him to the Savannah Bananas. In this special encore episode, recorded January 25, 2025, Jackson reveals how a promising baseball career came to an abrupt halt during COVID, why he started delivering groceries for Instacart, and how making TikToks eventually led to an opportunity with MLB. Then, after seeing three Savannah Bananas videos in one night, he decided to shoot his shot—and found his way back onto the baseball field. Jackson also takes us behind the scenes of Banana Ball, from choreographed dances and trick plays to the unexpected challenges…