Taylor Swift Revealed That Kenny Chesney’s Early Support Fueled Her Dreams

TIME’s 2023 Person of the Year, Taylor Swift, shared a special anecdote with Sam Lansky for her cover story in the magazine featuring Kenny Chesney. 

She was 17, freshly starting her music career, when she booked a career-changing slot opening for country superstar Kenny Chesney. That kind of big opportunity – arguably the biggest at that time for a budding musician like her – was hard to come by, and she was so excited that she got it. Unfortunately, she couldn’t ultimately participate in it because a beer company sponsored the tour. She was too young. 

View this post on Instagram

A post shared by Taylor Swift (@taylorswift)

RELATED: Uncover 10 Lesser-Known Facts About Kenny Chesney

She was devastated, to say the least, when her mother, Andrea, gave her the news. 

Then, at her 18th birthday party, Chesney’s promoter visited her and handed her a card from Chesney. Swift recalled it said how sorry he was she couldn’t come on the tour and wanted to make it up to her. 

Attached to the note was a check for more money than she had ever seen in her life. That money didn’t only pay her tour buses and band bonuses but also fueled her dreams. 

According to Chesney, he gave Swift that gift because she was what he called “a writer who had something to say.” It was something you couldn’t fake by writing clichés – you had to live it and write it as real as possible. 

View this post on Instagram

A post shared by Kenny Chesney (@kennychesney)

RELATED: A Look Back at Taylor Swift’s First Grand Ole Opry Performance

Following Swift’s interview, Chesney took to Instagram to congratulate the singer. He posted a throwback photo of Swift early in her career and another one with him. In the caption, he wrote a personal message to her. 

He penned, “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 continued, saying that it was awesome watching her shine. 

View this post on Instagram

A post shared by Entertainment Tonight (@entertainmenttonight)

He then went on to congratulate her for being named Person of the Year, and he was glad that the magazine finally saw what he had always loved about her, her music, and her art. He then signed off by saying he was proud of her and loved her. 

Seventeen-year-old Taylor Swift may have missed out on a big opportunity, but Kenny Chesney didn’t miss out on the talent in her. And look where she is right now: happy, successful, and thriving.