Jason Kelce Was Offered $100 to Say These 2 Words to Taylor Swift

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Jason Kelce is gearing up for the epic showdown at the 2025 Super Bowl, but not without a bit of humor along the way.

On Thursday, January 30, during the 94WIP Morning Show, Jason was offered a daring proposal from co-host Joe DeCamara: a chance to make $100 if he hugged his brother's girlfriend, Taylor Swift, and said "Go birds!" after an Eagles touchdown. The offer –– which was met with laughter from Jason –– comes just ahead of the Super Bowl match-up between Jason's former team, the Philadelphia Eagles, and his brother Travis's Kansas City Chiefs.

ESPN analyst Jason Kelce on set prior to the AFC Divisional playoff game between the Kansas City Chiefs and the Houston Texans at GEHA Field at Arrowhead Stadium on January 18, 2025 in Kansas City,... Aaron M. Sprecher/David Eulitt/Getty Images

"$100 to you. Saquon Barkley scores a touchdown. You hug Taylor Swift and say, 'Go birds!'" DeCamara jested. His remark followed up his explanation about how Swift's booth always goes crazy during the touchdowns: "The hugs are going all over the place. Goes viral."

While the offer was light-hearted, the tension and excitement of the big game are anything but. Jason, 37, laughed off the suggestion with Swift, 35, but acknowledged the connection the pop star has to Philadelphia, as she grew up a fan of the Eagles before her relationship with Travis, also 35.

"She grew up here," Jason acknowledged. "She knows that everybody's cheering for this weekend. She's obviously on the other side of it, but, yeah, no. It's going to be fun.

Taylor Swift celebrates with Travis Kelce #87 of the Kansas City Chiefs after defeating the Buffalo Bills 32-29 in the AFC Championship Game at GEHA Field at Arrowhead Stadium on January 26, 2025 in Kansas... Jamie Squire/Getty Images

Jason, who played for the Eagles from 2011 until his retirement in 2024, has made it clear that while he will root for both teams, the rivalry will remain friendly. On an episode of his and Travis' New Heights podcast on Wednesday, January 28, he said, "I'll always root for my brother. That's the reality of it ... I'm always going to root for Travis."

Jason's wife Kylie Kelce also seems to be in a tricky situation with their three daughters ahead of the big game, as she shared on the Thursday episode of her podcast, Not Gonna Lie. To avoid team-related tension for Wyatt, 5, Elliotte, 3, and Bennett, 1, Kylie –– who is also pregnant with her and Jason's fourth daughter –– decided to dress them in "Go Uncle Trav" shirts to support Travis, while acknowledging their love for the Eagles. "They love their uncle, and of course, they love cheering him on. To be fair, they love cheering on the Birds too. But he is our family," she shared. Kylie also explained that while she's always supported both teams, her connection to the Eagles runs deep as a Philadelphia native, saying she was "raised to bleed green."