ESPYS 2026: Maggie Sajak Reacts to Boyfriend Jackson Olson on DWTS

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.