Who Is ‘Wheel of Fortune’ Star Maggie Sajak’s New Boyfriend? Meet Savannah Bananas’ Jackson Olson
Talk about a hard launch! Wheel of Fortune‘s Maggie Sajak has gone official with her new boyfriend, Jackson Olson.
Pat Sajak‘s daughter and the social correspondent for the beloved game show went public with her new man on April 21 in an Instagram post. The couple posted an adorable photo that featured them posing in front of the Cinderella Castle at Walt Disney World in Orlando, Florida. “Applications closed,” they captioned their joint announcement.
So, who is Jackson Olson? Swooon has all the key details you need to know about Maggie Sajak’s new boyfriend. If you’re a fan of the Savannah Bananas, you’ll definitely recognize Olson!
Who is Maggie Sajak’s boyfriend?
Maggie Sajak is currently dating Jackson Olson. The 28-year-old hails from Connecticut, and he’s amassed quite the social media following. (More on his job below.) He has over one million followers on Instagram and two million on TikTok.
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It’s unclear how Sajack and Olson met, but they seem very happy together. In addition to the hard launch, Olson shared a clip of Will Ferrell‘s Elf character saying, “I’m in love. I’m in love. And I don’t care who knows it.” He wrote over the top, “Me right now.”
@jacksonolson_ Not sure if this will help me or hurt me 😠#single #dating ♬ original sound – thesavbananas
In December 2025, Olson admitted that he’d been single for over five years, so he decided to reveal his “2026 boyfriend application” to the world. “Not sure if this will help or hurt me,” he captioned the video. This time around, it certainly helped! Olson took a big swing, and it paid off!
What does Jackson Olson do for a living?
Olson is an infielder for the Savannah Bananas, an exhibition barnstorming baseball team based in Savannah, Georgia. This isn’t your traditional Major League baseball team. The Savannah Bananas specialize in Banana Ball, which is all about putting fans first. The team tours all across the country.
Olson has been a part of the Savannah Bananas since 2022. He also played college baseball at the University of Hartford and Stetson University.
Who has Maggie Sajak dated in the past?
Sajak, 31, was previously linked to actor Ross McCall, who is 19 years her senior. They were spotted out together in March 2024 and kept their relationship very low-key. In September 2024, McCall briefly discussed his relationship but didn’t mention Sajak by name. “It’s early,” he said on Jenny Mollen‘s All the Fails podcast.
