Taylor Swift and Kenny Chesney go way back.
As the pop star discussed in her interview for Time Person of the Year, Chesney supported her at the very beginning of her career. Now, after she’s come so far, he’s taking the opportunity to support her again.
“Taylor, I knew looking in your eyes that first time on stage with us, you had ‘it,’” he wrote on Instagram. “The hunger, that something special… A gift not everyone has to connect. It’s been awesome watching you shine! Congratulations on being @TIME’s Person of the Year.”
He added, “I’m glad TIME sees what I’ve always loved about your music, your art and you as a human being. I’m so proud of you and I love you.”
The story that Swift told Time was that when she was 17, Chesney offered her a spot opening for him on a tour.
“This was going to change my career,” she said. “I was so excited.”
She then said that a couple of weeks later, she found her mother “weeping” like “there had been a family emergency.” Her mother explained to her that she wasn’t able to go on the tour because it was sponsored by a beer company, and she was too young to participate. She was “devastated,” she said.
Later, she ran into Chesney’s promoter at her 18th birthday party, and he had something to give her: a note from Chesney. As she remembered, he’d written, “I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you.” Along with the card, he’d given her a check.
“It was for more money than I’d ever seen in my life,” she explained. “I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams.”
The “She’s Got It All” singer also spoke to Time, saying that he had sent that check because “She was a writer who had something to say. That isn’t something you can fake by writing clichés. You can only live it, then write it as real as possible.”
Despite the fact that Chesney had to rescind his offer for Swift to join him on tour back then, they maintained their friendship.
In 2011, Swift told Taste of Country, “He is one of the coolest, most affectionate, gracious people that I’ve met in the music industry, and he’s always reaching out to me to say ‘hey’ and check up on me and see how I’m doing. It seems like he has this weird intuition to know when I need someone to stop in and say, ‘How are you.'”
Weeks after that, Chesney told the same outlet, “Taylor and I are very good friends, and I’ve known her for a while, and I know the ups and downs that an artist goes through.”
He also mentioned the gifted money in the 2011 interview.
“So, I’m backstage and I come up behind her and gave her a hug and said, ‘I want my money back,'” he said. “I haven’t gotten it back yet, but maybe I will one day, who knows.”