2023PERSON OF THE YEAR Taylor Swift 35 MINUTE READ

Taylor Swift is telling me a story, and when Taylor Swift tells you a story, you listen, because you know it’s going to be good—not only because she’s had an extraordinary life, but because she’s an extraordinary storyteller. This one is about a time she got her heart broken, although not in the way you might expect.

She was 17, she says, and she had booked the biggest opportunity of her life so far—a highly coveted slot opening for country superstar Kenny Chesney on tour. “This was going to change my career,” she remembers. “I was so excited.” But a couple weeks later, Swift arrived home to find her mother Andrea sitting on the front steps of their house. “She was weeping,” Swift says. “Her head was in her hands as if there had been a family emergency.” Through sobs, Andrea told her daughter that Chesney’s tour had been sponsored by a beer company. Taylor was too young to join. “I was devastated,” Swift says.

But some months later, at Swift’s 18th birthday party, she saw Chesney’s promoter. He handed her a card from Chesney that read, as Swift recalls, “I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you.” With the note was a check. “It was for more money than I’d ever seen in my life,” Swift says. “I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams.”

2023PERSON OF THE YEAR Taylor Swift 35 MINUTE READ