Kenny Chesney Once Told Taylor Swift to Give His Money Back After Their Joint Tour Was Canceled

Taylor Swift and Kenny Chesney's friendship did not start off on the best of terms and involved a loss of money on Chesney's side.

The country star appeared on The Tonight Show Starring Jimmy Fallon on Jan. 16 where he recalled he once had to cancel a joint tour with Swift after giving her a large sum of money.

Chesney's story began when he shared that Swift booked a tour with him when she was just 17, however, things became complicated when the tour was sponsored by a beer company.

"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?" he said.

Chesney felt bad for Swift losing money as a result of her cancelled slot on the tour and decided to give her a generous gift instead.

"I gave her a specific amount of money... it was quite a bit of money, because I wanted to make it up to her," he recalled.

Soon after, Swift rose to superstardom thanks to the success of her debut album as well as the follow-up, 2008's mega-selling Fearless. Both artists were nominated at the CMA Awards for Entertainer of the Year, a category that Swift would go on to win. This led to an awkward moment between her and Chesney.

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

Chesney, 56, who has since been on good terms with Swift, supported her being TIME's Person of the Year in 2023.

"Taylor, I knew looking in your eyes that first time on stage with us, you had 'it.' 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," he wrote on Instagram.

Chesney appeared on the talk show to promote his upcoming residency at the Sphere in Las Vegas, which is slated to begin in May and last for 12 shows.

"I'm always looking for ways to deepen the way No Shoes Nation experiences this music. Over the years, they have shown me through their own response to these songs how passionate they are about what they mean, how these songs are part of their lives. When people give you that much heart, I want to give them even more," the singer said in a statement to People.

"To me, this is going to be a whole new way of rocking the fans, and I can't wait," he continued.

Tickets for the event go on sale on Jan. 31 and can be found at KennyChesney.com.

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Taylor Swift, Kenny Chesney