Jackson Olson has been making a name for himself long before his romance with Pat Sajak’s daughter Maggie Sajak.
Olson is best known for his role as a social media personality and player for the Savannah Bananas. 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 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.
