Jackson Olson of Savannah Bananas Goes Public With Maggie Sajak

Jackson Olson is no longer on the market. The 28-year-old baseball player and entertainer for the Savannah Bananas made his relationship status official by publicly launching his romance with Maggie Sajak.

Maggie is the daughter of Pat Sajak, the longtime host of Wheel of Fortune, and has worked as a correspondent for the program throughout her career.

On Tuesday, April 21, Olson posted an Instagram photo showing him and Maggie posing in front of a castle at a Disney park during a recent trip. "Applications closed?," he wrote alongside the image.

The announcement marks a full circle moment for Olson, who went viral on TikTok in December 2025 when he posted a tongue-in-cheek video about his single status. In that clip, the baseball player joked that he had been single for more than five years and was formally opening applications for a girlfriend. The video included a playful promise of a Disneyland trip for whoever he ended up dating.

Olson is the standout player for the Savannah Bananas, an exhibition baseball team known for playing Banana Ball, a variation on the traditional sport. The squad has built a significant following through their entertaining TikTok videos and social media presence.

With his recent relationship confirmation, Olson appears to have followed through on his viral promise from months earlier.