Jackson Olson has been making a name for himself long before his romance with Pat Sajak’s daughter Maggie Sajak. While the Wheel of Fortune host’s daughter has been in the public eye for years, Olson’s journey from college baseball to viral TikTok sensation and now a high-profile relationship has captured attention across social media and sports circles.
Olson is best known for his role as a social media personality and player for the Savannah Bananas, a baseball team known for its quirky, high-energy approach to the game. Amid the Bananas’ growing online popularity, Olson has become a standout player on the team. The athlete has gone viral multiple times thanks to his Taylor Swift-inspired lip syncs and shameless ability to poke fun at his (once) lack of a dating life.
Last year, Olson posted a TikTok video saying he was tired of being “single for over five years,” adding that he’s ready for someone to call him “boyfriend.” Olson’s December 2025 post went viral, as thousands of women attempted to shoot their shot in the comments section.
Four months later, Olson’s wish came true when he and Maggie hard-launched their relationship. “Applications closed✅,” Olson wrote via Instagram in April 2026 alongside a photo of him and Maggie at Disney World.
Keep scrolling for everything to know about Olson amid his new romance:
Jackson Olson Played College Baseball
Olson was an infielder for the University of Hartford from 2017 to 2020. The following year, he attended Stetson University, where he played college baseball for one season. In his collegiate career, Olson earned a .288 batting average.
Upon graduation, Olson had dreams of joining the MLB but was not selected due to a shortened MLB draft caused by the COVID-19 pandemic.
Jackson Olson Has a Big TikTok Following
After putting his MLB dreams on hold, Olson started making videos on TikTok. He launched his page by creating silly — yet relatable — videos about delivering groceries, which quickly gained traction. His content often blends humor with sports culture, including skits about baseball tryouts and playful jabs at his own dating history.
One of his most viral moments came when he recreated a scene from the movie The Proposal with a baseball twist, lip-syncing to Taylor Swift’s “Love Story” while holding a bat. The video racked up millions of views and cemented his status as a fan favorite.
How Jackson Olson and Maggie Sajak Met
Olson and Maggie Sajak’s relationship began in 2025, though the exact details of their meeting remain private. However, their public appearances and social media posts have hinted at a growing bond. Maggie, who has her own following as a fashion and lifestyle influencer, has been seen supporting Olson’s career, including attending Savannah Bananas games and sharing behind-the-scenes moments with him.
The couple’s dynamic has drawn comparisons to other celebrity relationships, with fans noting their playful chemistry. Olson’s lighthearted approach to life and Maggie’s polished public persona create a contrast that keeps their relationship intriguing.
As Olson continues to balance his baseball career with his growing social media presence, his relationship with Maggie Sajak has become a focal point for fans. Whether it’s his viral TikTok content, his college baseball stats, or his new romance, Jackson Olson is a name that’s
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