The “When the Sun Goes Down” artist shared a sweet message for Swift after she gave him a shout-out in her interview for the annual honor.
“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,” wrote on Instagram Wednesday, alongside photos of him and a young Swift.
“It’s been awesome watching you shine!” he added. “Congratulations on being @TIME’s Person of the Year. 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.”
In her Person of the Year interview, the “All Too Well” singer shared a story about scoring a gig as Chesney’s opening act when she was 17.
“This was going to change my career,” she said. However, the young singer-songwriter was ultimately unable to join the tour because it had been sponsored by a beer company and she was too young.
At her 18th birthday party, the “Cruel Summer” artist, who has since crossed over from country music to pop superstardom, was approached by Chesney’s promoter who handed her a card from the “You and Tequila” singer.
“I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you,” the card read, as Swift recalled.
Inside the card was a check, she said, “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,” she added.
The “She Thinks My Tractor’s Sexy” singer told Time that he gave Swift the card and check because he believed in her gift of storytelling and felt she had a real future in the industry.
“She was a writer who had something to say,” he said. “That isn’t something you can fake by writing clichés. You can only live it, then write it as real as possible.”
After notching the Person of the Year honorific, Swift became the first woman to appear twice on the magazine’s annual cover since the series began in 1927.
The “Karma” singer, 33, made her Person of the Year cover debut in 2017 among the “Silence Breakers,” a group of women who helped spark a cultural reckoning around sexual harassment and assault. She appeared alongside California lobbyist Adama Iwu, actor Ashley Judd, a strawberry picker identified as Isabel Pascual and software engineer Susan Fowler.
“This is the proudest and happiest I’ve ever felt, and the most creatively fulfilled and free I’ve ever been,” Swift said in Wednesday’s cover story.