• Jackson Olson, second baseman for the Savannah Bananas, has been cast on Dancing With the Stars Season 35.
• The announcement was made during Disney’s Upfront presentation on Tuesday.
• Olson joins previously announced contestants Maura Higgins and Ciara Miller as the third celebrity revealed.
• Fans suspected the casting after DWTS judge Derek Hough tossed Olson a mini Mirrorball at a Bananas game in March.
• His casting is part of a larger Disney-Savannah Bananas partnership that includes the Banana Bowl streaming live on Disney+ this October.

Jackson Olson is trading the baseball diamond for the ballroom. The Savannah Bananas second baseman and social media star has been officially cast on Dancing With the Stars Season 35, Disney announced Tuesday during its Upfront presentation — and honestly, fans had already figured it out.

Olson becomes the third celebrity confirmed for the upcoming season, joining The Traitors and Love Island breakout Maura Higgins and Summer House fan favorite Ciara Miller. The full cast of celebrities and their professional dance partners will be revealed on September 2, exclusively on Good Morning America.

The Clues Were There All Along

In the weeks before the announcement, eagle-eyed fans were already connecting the dots. Olson posted a TikTok of himself dancing on the baseball field, with text over the video reading, “Jackson when can you share the secret you’ve been keeping from us?” He captioned it simply: “You’ll find out soon! 😅 #secret #baseball.” Sharp-eyed viewers immediately spotted a disco ball tucked on the fence behind him. “Yall it’s a mirrorball!!” one commenter wrote. Another added, “Guess I’m going to watch DWTS now 😏.”

The speculation went even deeper than that. Back in March, DWTS judge Derek Hough performed alongside Olson at a Savannah Bananas game — and in a video of the performance shared to Instagram, Hough tossed Olson a mini Mirrorball. The comment section basically solved the mystery on the spot: “OMG…Jackson is about to be on DWTS.”

From the Diamondbacks to the Bananas to the Ballroom

Olson’s road to this moment has been anything but a straight line. He turned down an offer from the Arizona Diamondbacks to finish his college degree, then transferred from the University of Hartford to Stetson University after the MLB draft was shortened during the pandemic. When his college career ended, he thought that was it for baseball.

“I thought I was done with baseball after my career at Stetson University,” Olson told People in 2023. “Mentally, I kind of fell out of love with the game. And the Bananas brought that back.”

He rebuilt his relationship with the sport through content creation — sharing baseball insights alongside stories about food, family, and relationships — and built a following of more than 2 million on TikTok in the process. That online presence eventually caught the attention of Savannah Bananas owner Jesse Cole, and Olson earned a spot on the roster of the Georgia-based team known for turning every game into a full-on entertainment spectacle. Think choreographed dances to Taylor Swift and Mariah Carey, comedy sketches, and Broadway-level showmanship from first pitch to final out. His teammate Derek Klena, of Broadway fame, is right there alongside him.

In other words: this is not a man who has never danced in front of a crowd.

A Big Disney Moment — On and Off the Field

Olson’s DWTS casting is just one piece of a much bigger announcement. Disney revealed an expanded partnership with the Savannah Bananas at the same Upfront event, making Disney+ the exclusive U.S. home of the Banana Bowl — the league’s championship game — streaming live this October. ESPN, Disney+, and the Bananas have also launched a 25-game exclusive package, with every game streaming on the ESPN App and Disney+, and select matchups airing across ESPN networks and ABC.

For the show itself, the momentum couldn’t be better. Season 34 — hosted by Alfonso Ribeiro and Julianne Hough, with judges Carrie Ann Inaba, Bruno Tonioli, and Derek Hough — finished as the No. 1 entertainment series among adults 18-49 for the second year running. Ratings in the key broadcast demo grew nearly 80% year-over-year. The finale alone pulled in 72 million votes, with nearly half a billion cast across the entire season. Robert Irwin and Witney Carson took home the Mirrorball that year.

ABC SVP of content strategy Ari Goldman made clear the network plans to keep pushing on the social media front that helped drive that growth. “The team has innovated immensely in the social media space, both from a casting perspective and a lot of the social and marketing tactics involved with the show,” Goldman told TheWrap. “I think you’re going to see the same type of approach this season.”

Casting someone with 2 million TikTok followers who already dances at work every day? That tracks.

Life Off the Field Is Pretty Good Too

Olson has been making headlines beyond baseball lately, thanks to his relationship with Maggie Sajak — yes, daughter of Wheel of Fortune legend Pat Sajak. The two went public in April, and Olson has been refreshingly open about making it work across the miles.

“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 told Us Weekly earlier this month. “I feel like in any relationship, you’re trying to figure out how to see each other as frequently as possible, which is never something that I thought in my past I was going to want to do… but now I really do.”

The full Season 35 cast drops September 2 on Good Morning America. Until then, that mini Mirrorball Derek Hough tossed him back in March is looking more and more like a prophecy.

The post Savannah Bananas’ Jackson Olson Joins DWTS Season 35 appeared first on Cream.

• Maggie Sajak, 31, cheered on boyfriend Jackson Olson at the 2026 Banana Ball World Tour
• Olson kissed Sajak on the forehead in a sweet post-game photo the couple both shared to their Instagram Stories
• The two hard-launched their relationship at Disney World on April 21
• Olson opened up about the long-distance dynamic — he’s based in Georgia, she’s in Los Angeles
• Sajak works as Wheel of Fortune’s social correspondent; Olson plays for the Savannah Bananas

Maggie Sajak was front and center for one of Jackson Olson’s biggest moments yet — and the photos prove she’s exactly the kind of girlfriend who shows up.

The Wheel of Fortune social correspondent, 31, was spotted in the stands cheering on her Savannah Bananas boyfriend during the 2026 Banana Ball World Tour, and the couple made sure to document the moment. Olson leaned in and kissed Sajak on the forehead in a sweet post-game photo, while she beamed in a yellow top — yes, the team’s official color — and denim jeans. Whether that outfit was intentional or just a happy coincidence, fans are choosing to believe she planned it.

Both Olson and Sajak shared the photos to their Instagram Stories and set them to Taylor Swift’s “Opalite.” Because of course they did.

The comments were just as warm as the moment itself. Olson’s Bananas teammate Alex “Ziggy” Ziegler dropped an “Ily guys” in the comment section, and Schmigadoon! actor Derek Klena kept it simple with “QT’s.” Honestly, same.

From Disney World to the Banana Ball Tour

The couple only went public about a month ago. On April 21, Olson surprised fans when he hard-launched the relationship during a trip to Disney World in Florida. His caption said everything it needed to: “Applications closed✅” — a nod to the viral “boyfriend application” moment that had already made him something of a folk hero on social media.

Since then, the two have been navigating what any new couple would consider a logistical challenge. Olson is based in Georgia with the Bananas. Sajak lives in Los Angeles, where she works in her role with Wheel of Fortune. Two different coasts, two very different schedules.

But Olson, for one, isn’t complaining. “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 told Us Weekly exclusively on May 1. “I feel like in any relationship, you’re trying to figure out how to see each other as frequently as possible, which is never something that I thought in my past I was going to want to do… but now I really do.”

The Pressure of Playing in Front of Someone You Care About

Having your girlfriend in the stands is cute. Having your girlfriend in the stands when your job involves trick baseball and the entire crowd is watching? That’s a different kind of pressure.

Olson admitted he feels it. “I start sweating and I’m like, ‘I can’t strike out because then I have to hit a home run,'” he said, laughing. “Even though I do strike out a decent amount.”

But he’s found his footing. “I’ve gotten that out of the way of, like, the nerves there. Every person that I care about in my life has seen me play with the Bananas now, so it’s smooth sailing. If I play poorly, whatever, it’s life. We’re not playing for a World Series here.”

That’s the Savannah Bananas ethos in a nutshell — fans first, rules bent, fun mandatory. And it sounds like Sajak, daughter of the legendary Wheel of Fortune host Pat Sajak, fits right into that world. She showed up in team colors, cheered her guy on, and posted the Taylor Swift soundtrack to prove it.

The forehead kiss, though? That one’s going to live rent-free in fans’ heads for a while.

The post Maggie Sajak Cheers On Boyfriend Jackson Olson at Savannah Bananas Game appeared first on Cream.