Watch: Why Kenny Chesney Gave 'Quite A Bit Of Money' To Taylor Swift

Kenny Chesney remembered the time he had to tell Taylor Swift she couldn’t join him on tour.

Chesney appeared on The Tonight Show Starring Jimmy Fallon on Thursday evening (January 16), hours after announcing his 12-show headlining run at Sphere Las Vegas. Jimmy Fallon brought up Swift’s “sweet story” about Chesney when she was revealed as TIME’s Person Of The Year. Swift credited Chesney with “fuel[ing] my dreams,” because of the way he responded when a “devastated” Swift, then 17, had to miss the tour.

“She was a kid,” Chesney said.” Taylor was — we booked Taylor to go out on the road with us. This was several years ago, obviously. But that summer, my tour was sponsored by a beer company, and they came to us right before the tour started and said, ‘we can’t have a minor on the tour,’ which made sense.

“But I had to call Taylor personally and tell her she couldn’t go on tour with me, which now seems absurd, right? So, I called her (and) told her she couldn’t go on the road. But I said, ‘look, I feel terrible,’ because she was gonna lose some money, and I gave her a specific amount of money. It was quite a bit of money because I wanted to make it up to her, right?” Chesney recalled. “And that year, later that year, we were both nominated for CMA Entertainer of the Year. That’s how hot she was. Well, she won. So, backstage, I went up to her and gave her a big hug. I said ‘congratulations, but give me my money back.’”

Swift’s victory at the CMA Awards — she won that category in 2009 and again in 2011 — marked the final time a female artist would score the coveted honor in more than a decade. Twelve years later, Bell Bottom Country trailblazer Lainey Wilson won Entertainer of the Year. Chesney said he always knew Swift had the qualities that make up a superstar artist.

“I knew she had something,” Chesney told Fallon. “I knew that she was very driven. I knew that she was a really good songwriter. ...Nobody knows, you know, really that a person has the ability to really touch the world like Taylor has, and brought a lot of people together and has given the world — you know, sports and music bring people together more than anything we have. I truly believe that.”

When Swift, now a global powerhouse, was named TIME’s Person Of The Year, she wrote that she received the check from Chesney on her 18th birthday. She said the check was “for more money than I’d ever seen in my life,” Swift recalled. “I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams.”

“Taylor, I knew looking in your eyes that first time on stage with us, you had ‘it,’” Chesney wrote in a tribute to Swift in December 2023. “The hunger, that something special… A gift not everyone has to connect. It’s been awesome watching you shine! Congratulations on being [TIME]’s Person of the Year. I’m glad TIME sees what I’ve always loved about your music, your art and you as a human being. I’m so proud of you and I love you.”