Maggie Sajak and Jackson Olson’s love story started at a Los Angeles Dodgers playoff game in October 2024, and it’s been unfolding in the spotlight ever since. The couple confirmed their relationship in April 2026, and by May, Olson had already met Maggie’s dad, former Wheel of Fortune host Pat Sajak. Casual, right?
Olson, a Savannah Bananas star, brought his signature chaotic energy to Dancing With the Stars season 35, dancing with pro partner Emma Slater. His Joker-themed contemporary routine wasn’t enough to keep him in the competition, and he was eliminated on October 27, 2026, alongside Tyler Cameron and Sharna Burgess. But the moment that really got fans talking came after the show, when Maggie posted a simple“So proud of you”message that had everyone swooning.
The whole saga is a perfect pop culture crossover: a game show family, a viral baseball league, and reality TV drama all wrapped into one couple. Olson has said he’s“a very weird person”who refuses to hold back, and honestly, that authenticity is what made his run memorable, elimination or not. So what do you think: should Jackson get a redemption season, or is one DWTS journey enough?
About the Author
Local Lawton
Local Lawton is a contributor to LocalBeat, covering local news and community stories.