Kenny Chesney recognized Taylor Swift’s talent early on when she was just a teenager slated to open for him on his 2007 Flip-Flop Summer Tour. Swift ultimately had to be removed from the lineup due to an alcohol sponsorship that prevented the underage artist from joining the tour, leading Chesney to compensate her with a check and a heartfelt note to make up for missing the shows. In his upcoming book, Heart Life Music (out Tuesday, Nov. 4), Chesney reflects on Swift’s creative drive and songwriting skills. “With Taylor, I mean, she had the eye of the tiger even as a teenager. And I recognized that early on,” Chesney recalls. “I could tell that she was really talented and really wanted it. And even at a young age, she was a really good songwriter. So I knew something special was going to happen there.” Chesney launched his 10-stop book tour on November 1 in Johnson City, Tennessee. (People)
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Kenny Chesney Recalls That He “Could Tell” Former Opener Taylor Swift Was “Special,” Even As A Teenager
By Erik Thompson
Nov 2, 2025 | 6:01 PM
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