How Kenny Chesney Made it Up to Taylor Swift After She Was Booted From His Tour

Kenny Chesney and Taylor Swift during 2007 CMT Music Awards - Backstage and Audience at The Curb Event Center at Belmont University in Nashville, Tennessee, United States. ***Exclusive*** (Photo by Rick Diamond/WireImage)

As she opens up about moments of heartbreak throughout her career in her Person of the Year interview, Taylor Swift is reflecting on what may have been the first big blow.

At just 17 years old, the now-superstar booked the gig of a lifetime (so far)—opening for Kenny Chesney. “This was going to change my career,” she recalled thinking at the time as she spoke to TIME's Sam Lansky. "I was so excited.”

But just a couple of weeks later, Swift returned home and found her mother sitting on their home's front stairs crying. “She was weeping," Swift remembered. “Her head was in her hands as if there had been a family emergency.” Andrea Swift was devastated for her daughter, because Chesney's tour had been sponsored by a beer company. As a result of the partnership, Swift was too young at the time to join them on the road.

The "Big Star" singer was determined to make it up to her, though, sending his promoter to her 18th birthday party a few months later. He handed her a card from Chesney, in which he'd written, to the best of Swift's recollection, “I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you.” Within the card was a check for an undisclosed sum that was "more money than [Swift had] ever seen in [her] life.” It allowed her not only to "fuel [her] dreams," but to pay bonuses to her band.

Even then, with just her debut album under her belt, Chesney saw where she was headed and was more than happy to support it. "She was a writer who had something to say,” he told Lansky. “That isn’t something you can fake by writing clichés. You can only live it, then write it as real as possible.”

And that, of course, is why we love her!

Next: Taylor Swift Offers Rare Insight Into Aftermath of Kim Kardashian’s ‘Fully Manufactured Frame Job’