Kenny Chesney knew Taylor Swift was talented ‘early on,’ but he didn’t know she ‘would help bring the world together’

Kenny Chesney and Taylor Swift perform onstage during Kenny Chesney's The Big Revival 2015 Tour kick-off for a 55 show run through August. Kenny Chesney and Taylor Swift in Nashville in March 2015. PHOTO: 

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It was simple for Kenny Chesney to see how talented Taylor Swift was, but he had no idea how much she would change music and the world.

In her most recent Time cover story, Swift wrote a sweet story about the country superstar, 55. In a new interview with USA Today, Chesney talked about how he first felt about the “Karma” artist, 34.

Swift, who was 17 at the time, was supposed to open for Chesney on his 2007 Flip-Flop Summer Tour, but she was later taken out of the shows because of her age after a beer company became the backer. “I was heartbroken,” she told Time.

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Kenny Chesney and Taylor Swift during 2007 CMT Music Awards - Backstage and Audience at The Curb Event Center at Belmont University in Nashville, Tennessee, United StatesKenny Chesney and Taylor Swift in Nashville in April 2007. 

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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.”

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

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Taylor Swift performs during "Taylor Swift | The Eras Tour" at the National Stadium on March 02, 2024 in Singapore. Taylor Swift performs in Singapore on March 2, 2024. 

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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.”

Chesney couldn’t see into the future, but he did see how talented Swift was when he almost brought her on tour. “I saw that early on, but I had no idea it would turn into this.” When she told me she couldn’t go on our tour but then showed up at a few shows and sang with me, I saw something in her eyes that you can’t teach, the singer said.

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Country artist Kenny Chesney attends day 3 of SiriusXM at Super Bowl LIV on January 31, 2020 Kenny Chesney in Miami in January 2020. 

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“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?”

Even though they haven’t worked together officially, they have performed together many times, including at many stops on Swift’s Speak Now Tour in 2011 and Chesney’s The Big Revival Tour in 2015.

Soon after Swift’s Time story came out in late 2023, Chesney said the same thing on Instagram. “When I saw you on stage for the first time with us, Taylor, I knew you had “it.” You had the hunger, that something special… “An ability to connect that not everyone has,” he wrote at the time. “I’m so proud of you and I love you.”