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Jackson Olson was already carving out his own niche before his relationship with Maggie Sajak, the daughter of renowned TV host Pat Sajak, caught public attention.
Olson is widely recognized as a dynamic social media influencer and a prominent player for the Savannah Bananas. As the team’s online fame skyrocketed, Olson emerged as a fan favorite. His viral moments, often featuring Taylor Swift-inspired lip-sync performances and a humorous take on his previous single status, have captivated audiences.
In a memorable TikTok post last year, Olson humorously lamented his “over five years” of singlehood, expressing his desire to finally be someone’s “boyfriend.” The December 2025 video struck a chord, garnering a flood of responses from admirers eager to catch his attention.
Just four months later, Olson’s romantic life took a turn when he and Maggie made their relationship official to the public.
In April 2026, Olson humorously declared, “Applications closed✅,” on Instagram, sharing a charming photo of himself and Maggie enjoying a day 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 via Instacart. Olson also posted clips of him traveling to various baseball stadiums. While posting his baseball-related content, he discovered the Savannah Bananas and ultimately caught their attention.
Olson has more than 2 million followers on TikTok at the time of publication.
Jackson Olson Has Played for the Savannah Bananas Since 2022
The Savannah Bananas are not your typical baseball team — instead, they play their own version of the game aptly titled “banana ball.” While the elements of America’s favorite pastime are ever-present, banana ball features a lot more dancing and singing compared to a typical MLB game. Olson joined the Savannah Bananas in 2022 after he went viral as a baseball influencer.
“I thought I was going to be this guy coming in [as] the TikTok kid [and] no one would like me [or] everybody would think ‘He’s just here to get views on his videos’ Hopefully the minds have changed,” he said in a 2024 YouTube video.
Olson is the team’s third baseman and has been nicknamed “The Greatest Showman” due to his love of musical theater and epic trick plays.
Jackson Olson Is a Big Swiftie
Olson has made it very clear that he is the biggest Swiftie on the Savannah Bananas roster. He has walked up to several of the pop star’s songs including “I Can Do It With a Broken Heart,” “The Fate of Ophelia,” “The Life of a Showgirl” and more. In a February 2026 video, Olson and Party Animals player Dalton Ponce got together to do the “Opailite” dance challenge.
Jackson Olson Went Viral For His ‘The Bachelor’ Prank
Before finding love with Maggie, Olson went viral for pranking his mom telling her that he was chosen to be the next Bachelor.
“I’m proud of you but it’s kind of weird,” Olson’s mom told her son in the May 2025 Instagram clip.
After some more teasing, Olson ultimately fessed up to his mom and shared he was “kidding.”
“She was NOT a fan of the marriage part 😭,” he captioned the video.