Maggie Sajak, the daughter of former Wheel of Fortune host Pat Sajak has confirmed her romance with Savannah Bananas player, Jackson Olson.
The pair made their relationship Instagram official on April 21, Olson captioned the post:
“”Applications closed.”
In the picture, both Sajak and Olson posed at Disney’s Cinderella Castle at Magic Kingdom. Sajak wore a white tee and a black skirt, while Olson was seen in gray Chicago shirt and black shorts. Sajak shared the post on her Instagram stories as well along with a heart emoji.
Olson is a professional baseball infielder/entertainer for the Savannah Bananas, a baseball team based in Georgia known for its theatrical, fun style of play. In December 2025, Olson announced that he was actively searching a girlfriend and stated that he had been single for five years.
Maggie was previously linked to Scottish actor Ross McCall who is 19 years her senior.
Continue to read for more details.
All you need to know about Maggie Sajak’s boyfriend Jackson Olson
Fans are keen to know more about Maggie Sajak’s newfound love interest, Jackson Olson ever since they confirmed their relationship.
Olson was born on October 6, 1997 in New Milford, Connecticut, US, making him 28 years old. He is three years younger to his girlfriend, Maggie who is 31 years old. His full name is Jackson Daniel Olson. His parents are Dan and Laura Olson. Jackson also has a brother named Alex and a sister named Ari.
His father was a baseball coach when he trained for the sport as a teenager. In an exclusive chat with the People magazine, he explained:
“I proved myself on the field, but also knowing that my dad treated every single kid, no matter what, no matter where they came from, their background, how good they were at baseball — [he] didn’t care. He always made sure to make them feel loved and to make them feel like they had a spot on our team.”
Jackson Olson’s parents often accompany him to many of his games and are proud of their son. His mother, Laura told People magazine:
“We’re just really proud of Jackson, and a lot of it was timing, but more so, it was really his skill, his ability, and just making that connection.”
Olson is a former collegiate baseball player who went to New Milford High School in Connecticut before joining the University of Hartford where he played for Hartford Hawks from 2017 and 2020. He was part of the team that won the first conference tournament in school history. He later transferred to Stetson University.
Jackson Olson has been nicknamed The Greatest Showman on his Savannah Bananas baseball team and has a massive following on TikTok and Instagram. He has over 1 million followers on his Instagram and over 2 million on TikTok. He reportedly joined Savannah Bananas in 2022 after going viral as a baseball influencer.
He is known for as a content creator who often shares content with his followers featuring his family, including his mom and dad. Last year, Olson shared a TikTok video, dancing at the baseball field while mouthing One Direction’s Kiss You. He explaining in an overlaid text that he was tired of being single for the last five years and announced his official 2026 “boyfriend application.”
Olson described in the text that he dances on baseball field for a living, and that he would like to take his girlfriend to Disney for a vacation. He also described himself as a huge Taylor Swift fan and explained his “unhealthy obsession with musicals” ending his note with a line that said that his parents are sick of him of not having a girlfriend.
Jackson Olson also said that he has Peter Pan syndrome and has a diet of a 12 year old kid. He added that he is unphotogenic but will definitely make his partner look photogenic.
Edited by Aastha Dass