Kenny Chesney recounted when he had to first book Taylor Swift for one of his tours, and later cancel her because the popstar was a minor at that time.
During his appearance on The Tonight Show Starring Jimmy Fallon, Chesney, 56, reminisced about having to remove Swift from his tour and praised how much she has grown as an artist after that.
When Swift, now 35, was set to tour with Chesney, the tour’s beer company sponsor objected 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?” Chesney recalled on the show Thursday.
Feeling terrible about the situation, Chesney gave her a “specific amount of money” to compensate for the lost opportunity.
Later that year, both Chesney and Swift were nominated for CMA Entertainer of the Year, and Swift took home the award.
“Backstage I went up to her and gave her a big hug. I said, ‘Congratulations but give me my money back,’” Chesney joked.
Swift touched on Chesney’s generosity in her 2023 TIME Person of the Year cover story.
She remembered the note Chesney sent with the news that had left her mother “weeping.”
The note read, “I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you,” and included a check. Swift said the check “was for more money than I’d ever seen in my life.”
With that support, Swift was able to pay her band bonuses, finance tour buses, and fuel her dreams. Chesney’s act of kindness clearly made a lasting impact on Swift’s career and journey to success.
