In an interview with People published on Saturday, Nov. 1, the country legend, 57, spoke about his impression of Swift when she was a teenager before making it big.
In 2007, Chesney invited Swift to open for him on his Flip-Flop Summer Tour. Unfortunately, Swift, 18, was unable to join him because she was still underage and the tour had a beer company sponsor.
He added, "And even at a young age, she was a really good songwriter. So I knew something special was going to happen there."
Taylor Swift and Kenny Chesney; Rick Diamond/Getty Images for Kenny Chesney"I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you," a note from Chesney read," Swift recounted during her 2023 Time Person of the Year cover story. "With the note was a check. It was for more money than I’d ever seen in my life."
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