Ali on the Run Show31 Dec 2025

857. Jackson Olson, Savannah Bananas Infielder & Runner

"I think there are a lot of athletes out there that are just so scared to show who they truly are and what they like because of their teammates and their coaches. And they're trying to get to the next level, and they're like, 'Oh well, if I like this then I'm not gonna get to the next level.' It's actually the opposite. You're probably gonna play better if you show who you truly are, because you're more free."

Everyone loves Jackson Olson. The Savannah Bananas infielder is on a mission to make baseball more fun — and he's doing just that. Jackson has made a name for himself playing Banana Ball, which is like the baseball version of the Harlem Globetrotters. The exhibition-style games include full-on performances with choreography, lip syncing, and walk-ups designed to delight the sold-out stadium crowds. In this conversation, Jackson talks about his road to the Bananas, and his road to becoming a runner. This fall, Jackson ran his first race — the Disney Wine & Dine 5K — and now he's training for a 10K in January while figuring out how running fits into his busy baseball season. Plus, talking Taylor Swift, Disney World, and how Jackson found his voice and his confidence.

FOLLOW JACKSON @jacksonolson_

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In this episode:

On identifying as a runner (2:40)
Jackson shares the journey to his first 5K, and his impressions of the running community (5:00)
Why Jackson turned down an offer to go pro out of college (13:55)
How Jackson learned to embrace his Disney-loving Swiftie side (20:40)
How Jackson became a Savannah Banana (29:30)
All about the theatrics behind the Bananas, including how Jackson pulled off his "Life of a Showgirl" walkup the day after The Life of a Showgirl was released (34:45)
What it was life living out a childhood dream: playing at Yankee Stadium (43:25)
Taylor Swift talk! (48:30)
Will we see Jackson on Dancing With the Stars? (58:00)
How Jackson is feeling heading into this season with the Bananas (1:02:00)

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