Inside the special friendship of Taylor Swift and Kenny Chesney: 'It's been awesome watching you shine'

'I’m so proud of you and I love you'

Taylor Swift’s next-level success is a direct product of her own hard work, dedication, talent and a little help from some supporters along the way.

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In a recent interview with TIME surrounding her record-breaking year, Taylor highlighted a number of her biggest supporters that have had life-changing roles in her journey, one of them being Country mega-star, Kenny Chesney.

In 2007, Swift shared she was presented the biggest opportunity of her career when she was offered an opening spot on Kenny Chesney’s tour telling TIME, "This was going to change my career, I was so excited."

What was sure to be a big break quickly turned into big heartbreak when Taylor received the news she could not be a part of the tour as it was sponsored by a beer company and she was underage.

While a “devastated” Swift got back to work to find another big break, she stayed top of mind for Chesney who ultimately reached out with another career-changing offer.

On Swift’s 18th birthday, Chesney presented her 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." Enclosed in the card was a large amount of money that Swift says was enough to “fuel my dreams.”

"It was for more money than I'd ever seen in my life," Swift shared. "I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams."

Fast forward to 2023 and Taylor’s dreams have enough fuel to last an eternity. The 33-year-old was recently named TIME’s 2023 Person of the Year — an appropriate accolade as she set out for world domination with a record-breaking year including two re-release albums, her dazzling Eras Tour, a concert film, and so much more.

Now a longtime friend and forever Swiftie, Kenny Chesney took to X to praise Swift for her accomplishments and reflect on first meeting her.

“Taylor, I knew looking in your eyes that first time on stage with us, you had ‘it,’ Chesney wrote. “The hunger, that something special… A gift not everyone has to connect. It’s been awesome watching you shine! Congratulations’s Person of the Year. I’m glad TIME sees what I’ve always loved about your music, your art & you as a human being. I’m so proud of you & I love you.”

Way to go Tay Tay!

Featured Image Photo Credit: Rick Diamond/Getty Images