Kenny Chesney Had To Boot A 17-Year Old Taylor Swift From His Tour Before It Even Started — But He Still Paid Her BIG TIME

Taylor Swift country music
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A very classy move from Kenny Chesney.

Taylor Swift was named TIME Magazine’s Person of the Year, and in a lengthy feature out today, she recalled a story from her very early days in country music.

When she was 17-years old, she had booked a huge gig opened for Kenny on tour. At the time, it was easily her most notable slot to date, and she knew it had potential to change her career:

“This was going to change my career. I was so excited.”

A couple weeks later, she remembers coming home and seeing her mom, Andrea, sitting on the front steps of their house crying with her hands over her face, clearly devastated.

Taylor says it was so shocking that she thought there had been a “family emergency,” but the reality was that Andrea had received word that a beer company was sponsoring Kenny’s tour, and because she was under 18, Taylor could no longer be an opener:

“She was weeping. Her head was in her hands as if there had been a family emergency. I was devastated.”

A few months later, Taylor turned 18, and at her birthday party, Kenny’s promoter was in attendance.

She says he handed her a card from Kenny with a hand-written apology for her not being able to go out on tour with him, in addition to a check that Taylor says was worth “more money than I’d ever seen in my life.”

With that, she was able to give her band bonuses, pay for their tour buses (which are a massive expense for touring artists), and ultimately, the money helped “fuel her dreams”:

“[It said] ‘I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you.’ It was 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. I was able to fuel my dreams.”

Not only is that an incredibly kind and generous move on Chesney’s behalf, he certainly has bragging rights now as he helped jump-start her career and give her the resources needed to make it big in country music.

Obviously, Taylor’s currently the biggest superstar on the planet, so it was a worthy investment and kind move that changed everything for a very young Taylor Swift.

And I’m not saying that money is the only reason she’s gotten where she is today by any means, but those kinds of things really can change everything for a smaller, up-and-coming artist, so hats off to Kenny for such a badass gesture.

The pair are still friends to this day, and Taylor even had Kenny as a surprise guest at her Nashville show on her Speak Now tour back in 2011:

Later, she surprised him to duet “Big Star” for the kickoff of his Big Revival tour in 2015:

A beer bottle on a dock



A beer bottle on a dock