How Jackson Olson from Savannah Bananas Landed a Spot on Season 35 of Dancing With the Stars

Jackson Olson Shifts from Outfield to Dance Floor on DWTS

Jackson Olson, a member of the Savannah Bananas, is set to swap the baseball field for the ballroom as he joins the cast of Dancing With the Stars (DWTS) for its upcoming 35th season. The announcement was made on May 12, with Olson expressing his excitement on Good Morning America.

“When I was a kid, I never thought any of this was possible, even playing for the Bananas or anything like that,” Olson, 28, stated during the broadcast. “I was a shy kid that never danced, never put myself out there, never entertained and found a passion for it. Now, I kind of manifested it.”

Olson’s journey from a reluctant dancer to a contestant on a national stage took a surprising turn when he humorously hinted at it on TikTok last year. “I posted a couple TikToks… just joking, ‘Pranking my coach that I was going to be on the show,’ never thinking it was a possibility,” he recalled. “When I posted it, I’m like, ‘Maybe there is a possibility.’”

As he prepares for the competition, Olson will be among notable personalities, including reality stars Maura Higgins and Ciara Miller. The full lineup of contestants is yet to be revealed.

Support for Olson comes from his girlfriend, Maggie Sajak, who shared her enthusiasm on social media. “Beyond proud of you @jacksonolson_,” Sajak wrote on her Instagram Stories. “The dance floor better get ready.” Olson recently revealed his relationship with Sajak, daughter of former Wheel of Fortune host Pat Sajak.

Reflecting on the unique dynamics of their relationship, Olson noted, “It’s really cool because we’re obviously living very different lives right now on the opposite side of the country, but we’re able to come together and just have an awesome relationship." He emphasized the importance of making time for each other, stating, “You only get one chance at a start of a relationship.”

Olson’s pride swelled further after Sajak attended one of his games with the Savannah Bananas. “I start sweating and I’m like, ‘I can’t strike out because then I have to hit a home run,’” he commented, adding, “Every person that I care about in my life has seen me play with the Bananas now, so it’s smooth sailing."

As the new season of Dancing With the Stars approaches, all eyes will be on Olson as he steps into this new chapter of his life.