Every breakout star has an origin story, and Jackson Olson‘s begins at the family dinner table in Connecticut. The Savannah Bananas infielder — now also dancing his way across national television — is the middle story of a household built on sport, patience and showing up. Meet Dan Olson and Laura Olson, the parents behind one of Banana Ball‘s most beloved players.
Jackson, born October 6, 1997, was raised in New Milford, Connecticut, alongside his brother Alex and sister Ari. Today he is an Infielder for the Georgia exhibition team famous for dance routines, trick plays and celebrity guests — and a contestant on Dancing with the Stars Season 35, partnered with professional dancer Emma Slater. But long before the yellow uniforms and the ballroom, there were two parents who treated sport as something a family does together.
(YESNetwork / Wikimedia Commons (CC BY 3.0))A Father Who Handed Out Gold Gloves
Dan Olson’s own sporting life started on the basketball court at the University of Wisconsin-Oshkosh. His working life, though, took him deep into baseball: he worked for Rawlings, the famous glove maker, in a role that put him on major-league fields presenting Gold Glove Award honours to some of the game’s greatest defenders — including Derek Jeter, Robinson Canó and Mark Teixeira.
Imagine growing up with those stories at home. Yet by Jackson’s account, what defined his father as a coach was not the famous names but the opposite instinct. Dan coached Jackson’s baseball teams until Jackson was a teenager, and his son remembers a dad who treated every kid on the roster exactly the same — who made each player feel they belonged on the team, whether they were the star or the last name on the lineup card.
(Will120 / Wikimedia Commons (CC BY-SA 4.0))The Road Through College — and Around the Draft
Jackson played college baseball at two schools, the University of Hartford and Stetson University, following the traditional path as far as it would take him. After college, he hoped to be drafted by a major-league team. The call never came — the moment when thousands of talented players quietly leave the game every year.
Jackson chose a different door. He built a large following on TikTok and Instagram, filming the joyful, personality-first side of baseball that traditional pathways rarely reward, and that audience led directly to the Savannah Bananas, who signed him in 2022. The team — part sport, part travelling show — turned out to be the perfect stage for a player whose talent had always come with entertainment attached.
(baseballmapper / Wikimedia Commons (CC0))Parents Who Didn’t Understand — and Backed Him Anyway
Jackson jokes that his parents did not understand his social-media career at first. A son filming himself for the internet did not resemble any career path Dan and Laura knew. But they backed him anyway — and that, more than any single piece of advice, is the thread running through this family’s story. Support came before comprehension.
These days they attend many of his games, and they are fixtures in his videos: family trips, including drinking around the world at Epcot, and surprise home visits that delight his followers precisely because the warmth on screen is obviously unscripted. Laura recently appeared in a video with Jackson and his dance partner Emma Slater ahead of the show’s Dedication Night in October 2026 — a fitting episode title for a family like this one.
‘Proud That He Stayed Genuine’
Laura told PEOPLE that the family is proud of Jackson — and, in particular, proud of how he has handled a kind of fame nobody in New Milford planned for. The pride, she said, is especially about the fact that he has stayed genuine and true to himself through it all.
It is a modest quote that explains an immodest career. The Bananas ask their players to be fully themselves in front of thousands of people every night; Dancing with the Stars asks the same under even brighter lights. Jackson Olson can do both, his story suggests, because he learned at home that belonging never depended on being the star — a lesson from a coach who treated every kid the same, and a family that shows up, cameras or not.
A Family Built for the Long Season
There is a rhythm to sporting families that outsiders rarely see: the early mornings, the drives, the seasons that organise a household’s calendar for years. The Olsons lived that rhythm through Dan’s basketball days, his Rawlings career and three children’s worth of school and youth sport in New Milford. Jackson’s path asked more of that rhythm than most — two college programmes, a draft that never called, and then a reinvention conducted largely on a phone screen, in front of an audience his parents could not initially see.
What the family provided through each turn was continuity. When the plan changed, the support did not. When the stage changed — from Connecticut diamonds to a Georgia ballpark where players dance between pitches, and then to a televised ballroom — the same two people were in the audience, in the videos, in the story. Athletes often credit their parents in acceptance speeches; Jackson’s career makes the credit visible weekly, in content his followers can watch.
Laura’s summary to PEOPLE deserves the last word here, because it reframes what success means in the Olson house. Not the uniform, not the audience size, not the television contract — but that their son stayed genuine and true to himself. By that measure, the family from New Milford is undefeated, and Jackson’s biggest seasons may still be ahead of him.
It helps, finally, to remember how young this chapter still is. Jackson joined the Bananas only in 2022; his ballroom run is happening now, in season 35; and his parents’ public role is growing alongside his rather than trailing behind it. Families of athletes often fade from the story once the career takes off. The Olsons are doing the opposite — becoming more present, more recognisable and more clearly central as the stages get bigger, which is usually what happens when the support was real all along.