Music
Taylor Swift got a major career opportunity to tour with Kenny Chesney early in her career. He later had to tell her she couldn’t join him.
In the early days of her career, Kenny Chesney hired Taylor Swift to open for him on tour. The opportunity was a thrill for her; she was still a teenager, and the job would expose her to a much larger audience. Unfortunately, she wasn’t able to tour with him in the end. Chesney spoke about why he had to replace Swift.
Kenny Chesney said he felt terrible about having to fire Taylor Swift
When Swift was 17, Chesney hired her to open for him on tour. She felt this was a life-changing opportunity, but it was taken away from her at the last moment. A beer company sponsored the tour and informed Chesney that he couldn’t bring a minor with him.
“They came to us right before the tour started and said, ‘We can’t have a minor on the tour,’” Chesney said, per Billboard. “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?”
The news came as a huge blow to Swift’s family.
“[My mom] was weeping,” Swift told Time. “Her head was in her hands as if there had been a family emergency.”
Kenny Chesney paid Taylor Swift to make up for her disappointment
Swift said she was “devastated” by the loss of the opportunity. Chesney tried to make it up to her, though.
“It was for more money than I’d ever seen in my life,” Swift said. “I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams.”
While Chesney didn’t share how much money he gave her, he confirmed that it was a lot.
“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 admitted that he later asked for his money back
Not long after this, Swift and Chesney were both nominated for Entertainer of the Year at the CMAs. Swift ended up taking home the award. Chesney congratulated her afterward. He jokingly asked for his money back.
“Well, she won,” Chesney said. “So, backstage, I went up to her and gave her a big hug. I said ‘Congratulations, but gimme my money back.’”
