Maggie Sajak is cheering on boyfriend Jackson Olson after his casting on season 35 of Dancing With the Stars, according to E! News. The daughter of former Wheel of Fortune host Pat Sajak said she is proud of what Olson is taking on next.
Speaking to USA Sports’ Renee Montgomery at the ESPYS 2026 in New York on July 15, Maggie said Olson “crushes everything he sets his mind to” and said she expects him to do the same in the ballroom. The couple publicly confirmed their relationship on Instagram in April.
Maggie also said she plans to support Olson throughout the competition. Olson, a player for the Savannah Bananas, will compete on the show alongside Ciara Miller, Maura Higgins, Guillermo Rodriguez and other celebrities yet to be announced.
Olson told the outlet his schedule will be demanding because he will be dancing on DWTS while still traveling for baseball games around the country. He said he and his pro partner will be making frequent red-eye flights between Los Angeles, New York and other stops on the Bananas’ tour for about five weeks.
Even with the packed schedule, Olson said his baseball experience may help him remember routines, though he expects the dancing itself to take some getting used to. He said he hopes to settle in once he gets guidance from his partner in the ballroom.
