Kenny Chesney Recalls Bait-and-Switch He Had to Pull on Taylor Swift Early in Her Career

Kenny Chesney is still holding out on Taylor Swift's IOU.

During an appearance on The Tonight Show Starring Jimmy Fallon, the country star recalled having to remove her from his tour and raved about how much she's grown as an artist.

When Swift, 35, was booked to go on tour with Chesney, 56, the tour was sponsored by a beer company when she was a minor. The company said she couldn't join him because she was only 17.

"I had to call Taylor personally and tell her she couldn’t go on tour with me, which now seems absurd, right?" he remembered on the show Thursday. However, Chesney felt awful about telling Swift she couldn't join him "because she was going to lose some money."

Related: Taylor Swift Gave a Whopping $197 Million in Bonuses to Eras Tour Performers, Crew on Top of Their Salaries (Exclusive)

To make up for the loss, the country singer gave her a "specific amount of money." Later that same year, Chesney and Swift were both nominated for CMA entertainer of the year. "Well, she won," Chesney continued.

"So backstage I went up to her and gave her a big hug. I said, 'Congratulations but give me my money back,'" he joked.

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In the 2023 TIME Person of the Year cover story, Swift alluded to Chesney's generosity. The 14-time Grammy winner recalled the note Chesney sent her with the news that left her mother "weeping."

"I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you," the note read, which included a check. With the note was a check. "It was for more money than I’d ever seen in my life," Swift said, as per TIME.

"I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams."

After the "You and Tequila" singer read it, he was "stunned" that Swift remembered what happened. "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," he told USA Today.

Chesney added that he knew Swift had "something" when he first met her. "I knew that she was very driven. I knew that she was a really good songwriter," he said while on Jimmy Fallon's show.

"Nobody knows that a person has the ability to really touch the world like Taylor has," he added.

Related: Travis Kelce Has the Most Supportive Response When Asked If Taylor Swift Is Getting Musical Inspiration From Him

Swift wrapped up her record-breaking, continent-spanning Eras Tour this past December.

Meanwhile, Chesney just announced a limited residency at the Sphere in Las Vegas, kicking off in May. "To me, this is going to be a whole new way of rocking the fans, and I can’t wait," he said of his upcoming performances.

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