Kenny Chesney revealed a bold prediction he once made about Taylor Swift while discussing his new book, Heart Life Music.

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.

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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.

“With Taylor, I mean, she had the eye of the tiger even as a teenager. And I recognized that early on,” Chesney told People. “You can’t look into a crystal ball [to] predict and see what happened to her, but I could tell that she was really talented and really wanted it.”

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

Of course, Chesney’s prediction was correct; today, Swift, now 35, has won 14 Grammy Awards and broken records left and right–including with her 12th studio album, The Life of a Showgirl. He even had a tiny bit to do with that success, because when Swift wasn’t able to join Chesney’s 2007 tour, he felt bad and wrote her a check that made a huge impact on her career.

“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.”

She added, “I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams.”

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