It was easy for Kenny Chesney to recognize Taylor Swift’s talent — but not the impact she would have on  music and the world at large.

After Swift told a sweet story about the country superstar, 55, in her recent Time cover story, Chesney opened up about his first impressions of the “Karma” singer, 34, in a new interview with USA Today.
Chesney’s 2007 Flip-Flop Summer Tour was originally meant to feature a then-17-year-old Swift as an opening act, but she was later removed from the concerts due to her age after a beer company became the sponsor. “I was devastated,” she recalled to Time.Determined to remedy the situation, the “Out Last Night” singer gifted Swift a note that read, “I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you,” she told the outlet, along with a check “for more money than I’d ever seen in my life.”

“I was able to pay my band bonuses. I was able to pay for my tour buses,” said Swift in the interview. “I was able to fuel my dreams.”

After reading the Time story, Chesney spoke to the “Lavender Haze” musician about the moment. “I texted her and told her thank you for the love, and I was stunned she remembered it,” he told USA Today.

Looking back, he certainly doesn’t regret giving her the money. “To see what she did with that and the person she is now and the artist she is now and the creator that she is now — it is unbelievable what she has become,” said Chesney.

“I love Taylor,” he continued. “She has such a creative soul and that’s where all of this started. Everything you see, the stadium shows and big performances, are great. But she is still, I believe, at heart, a songwriter. That is something no one can deny.”

While Chesney couldn’t predict the future, he recognized how talented Swift was upon nearly bringing her on tour. “I saw that early, but I didn’t know it would turn into this. When she couldn’t do our tour and then she surprised me at a couple of shows and came onstage to sing with me, I saw that look in her eyes that you can’t teach,” added the performer.

 “I told my promoter, ‘This child is going to be something one day,’” detailed Chesney. “But who can look into a crystal ball and know she would help bring the world together?”

While the pair hasn’t linked up for an official collaboration, they’ve joined one another on stage for numerous performances — including the Nashville stops of Swift’s 2011 Speak Now Tour and Chesney’s The Big Revival 2015 Tour.

Shortly after Swift’s Time story came out in late 2023, Chesney expressed a similar sentiment on Instagram. “Taylor, I knew looking in your eyes that first time on stage with us, you had ‘it.’ The hunger, that something special… A gift not everyone has to connect,” he wrote at the time. “I’m so proud of you and I love you.”