Kenny Chesney is still waiting for Taylor Swift to settle her debt. During an appearance on The Tonight Show Starring Jimmy Fallon, the country star reflected on the time he had to remove Swift from his tour and praised how much she has developed as an artist.
When Swift, who was 17 at the time, was booked to join Chesney’s tour, the event was sponsored by a beer company. Since she was still a minor, the company insisted that she could not participate.
Chesney recalled, “I had to call Taylor personally and tell her she couldn’t go on tour with me, which now seems absurd, right?” He added that he felt terrible about telling Swift she couldn’t be part of the tour, especially since it meant she would miss out on some money.
To make up for the loss, Chesney gave her a “specific amount of money.” Later that year, both Chesney and Swift were nominated for the CMA Entertainer of the Year award, which Swift won. Chesney joked, “So backstage I went up to her and gave her a big hug. I said, ‘Congratulations, but give me my money back.’”
In the 2023 TIME Person of the Year cover story, Swift shared a memory of Chesney’s generosity. She recalled a note he sent, which left her mother in tears.

The note read, “I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you,” and it included a check.
Swift described the check as being for “more money than I’d ever seen in my life.” She went on to say that it allowed her to pay her band bonuses, cover tour bus expenses, and continue pursuing her dreams.
Chesney was “stunned” that Swift still remembered that gesture. He expressed his amazement at the artist Swift has become today, saying, “To see what she did with that and the person she is now and the artist she is now and the creator that she is now — it is unbelievable what she has become.”
When Chesney first met Swift, he knew she had a special drive. “I knew that she was very driven. I knew that she was a really good songwriter,” he said. “Nobody knows that a person has the ability to really touch the world like Taylor has.”
Swift completed her record-breaking Eras Tour in December 2023, while Chesney has announced a limited residency at the Sphere in Las Vegas, set to begin in May. He expressed his excitement for the upcoming shows, saying, “To me, this is going to be a whole new way of rocking the fans, and I can’t wait.”