How Maggie Sajak Feels About Boyfriend Jackson Olson's DWTS Casting

At the ESPY Awards 2026, Pat Sajak's daughter Maggie Sajak exclusively shared with E! News her reaction to boyfriend Jackson Olson joining Dancing With the Stars season 35.

How Maggie Sajak Feels About Boyfriend Jackson Olson's 'DWTS' Casting (Exclusive)

Dancing With the Stars really did spin and win by casting Jackson Olson.

At least, according to his girlfriend Maggie Sajak—daughter of former Wheel of Fortune host Pat Sajak—who couldn't be more proud of Jackson's decision to hit the ballroom this fall on season 35 of DWTS.

"He crushes everything he sets his mind to," she exclusively told USA Sports' Renee Montgomery at ESPYS 2026 in New York on July 15. "I'm excited to see him crush it in the ballroom."

And Maggie—who hard launched their romance on Instagram in April—is planning to be by his side for the whole experience as the Savannah Bananas baseball player competes alongside Ciara Miller, Maura Higgins, Guillermo Rodriguez and more celebrities who've yet to be announced.

"I'm just so excited to support him through this whole journey," Maggie added. "It's going to be amazing."

And the journey will be a bit bananas for Jackson, who explained that he will be performing on DWTS while also playing regular baseball games across the country.

"Whoever my [pro dancing] partner is will come with me on our Bananas tour, and we'll take red-eye flights for five weeks back and forth, L.A., New York, L.A., and wherever we're playing to," he noted at the ESPYS. "So, it's going to be crazy."

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Although his career as an athlete makes his schedule a bit slippery, Jackson is hoping the dance moves he's learned with the Savannah Bananas translate to DWTS—and perhaps earn him the Mirrorball Trophy.

"It's definitely going to help a little bit with memorizing moves, but doing the actual moves? Well, that's going to be a little tough and a little getting used to," Jackson continued. "I feel like I don't have any dance moves mastered. But once I get in the ballroom and get a little bit of my partner giving me some advice, I'll be good."

To see who else got in the groove at the ESPY Awards 2026, read on.

(E! and USA Sports are both part of the Versant Media family.)