Taylor Swift never forgot the way Kenny Chesney supported her after she had an early blow to her career.
At 17, Taylor Swift was just beginning her climb to music stardom. With singles like Tim McGraw and Teardrops on My Guitar doing well on the airwaves, she had forged a spot in the industry, and she was looking for ways to hold that spot.
Then a big break came in 2009. Taylor was offered the opportunity to open for Kenny’s summer tour, which “was going to change” her career, she told Time Magazine in December 2024. But when a beer company joined the tour as a sponsor, she could no longer be on the bill because of her age.
“I was devastated,” she admitted.
Despite Kenny Chesney being a much larger star at the time, he didn’t forget Taylor’s bad luck. So for her 18th birthday, he had his promoter show up to her party with a card that read, “I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you.”
Inside the card was a massive check.
“It was for more money than I’d ever seen in my life,” she said. “I was able to pay my band bonuses; I was able to pay for my tour buses. I was able to fuel my dreams.”
Kenny Chesney Believes Taylor Swift Helped “Bring the World Together”
In a March 20 interview with USA Today, Kenny Chesney said he was shocked to see that she’d mentioned him in the interview and admitted that he had even more respect for her after learning how she spent 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,” he told the publication.
“I love Taylor,” he added. “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.”
Kenny Chesney knew she would be a star back when she was supposed to open for him, but he could never have known just how big of a star she’d be.
“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,” he said.
“I told my promoter, ‘This child is going to be something one day,'” he added. “But who can look into a crystal ball and know she would help bring the world together?”
This story’s featured image is by Rick Diamond/Getty Images for Kenny Chesney.
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