How Kenny Chesney ‘Could Tell’ Former Opener Taylor Swift Was ‘Special’ (Exclusive)

Kenny Chesney and Taylor Swift go way back.

The country icon, 57, and the global superstar, 35, have had a long standing professional relationship, dating all the way back to 2007 when Swift was supposed to hit the road with Chesney as his opening act.

In Chesney’s latest project, a book titled Heart Life Music (out Nov. 4), the “You and Tequila” singer re-tells the story of that Flip-Flop Summer Tour, when, after a beer company became one of the sponsors, Swift had to be removed from the concerts since she was still a minor. In order to make things right, Chesney cut the then up-and-coming artist a check.

“With Taylor, I mean, she had the eye of the tiger even as a teenager. And I recognized that early on. You can’t look into a crystal ball predict and see what happened to her, but I could tell that she was really talented and really wanted it,” Chesney exclusively tells PEOPLE. “And even at a young age, she was a really good songwriter. So I knew something special was going to happen there.”

After Swift told the sweet story about the country legend in her 2023Time cover story, Chesney opened up about his first impressions of Swift in a 2024 interview with USA Today.

Along with the check, the “Out Last Night” singer gifted Swift a note that read, “I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you,” she told Time.

“I was able to pay my band bonuses. I was able to pay for my tour buses,” Swift said in the interview. “I was able to fuel my dreams.”

After reading the Time story, Chesney spoke to Swift about the moment. “I texted her and told her thank you for the love, and I was stunned she remembered it,” he told USA Today.

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During his more than 30-year career, Chesney has developed quite an eye for identifying the next generation of artists, in addition to Swift. He happened to grow up in the same Tennessee hometown as Kelsea Ballerini, “and we have a really strong connection because of that, and we have a song together, and we’ve become really good friends over the years,” he tells PEOPLE.

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Then, in 2024, Chesney brought Megan Moroney — whose star has since only continued to rise — on his Sun Goes Down Tour.

“I didn’t know Megan before we went out on the road in 2024 at all, and I say in the book that I almost regretted the decision because I didn’t want to set her up to fail. She only had one song. But when she got out there, I mean, she hit the stage like she designed it,” he says. “And I didn’t see that coming, all the fun we had with her. She and I became really great friends.”

Chesney and Moroney are nominated for Musical Event of the Year for their song “You Had to Be There” at this year’s CMA Awards, and Chesney says the “Am I Okay?” singer is the real deal.

“Megan’s fantastic. I mean, her personality is one of the reasons that she connects so well with her audience,” he says. “Yes, she’s an incredible songwriter, a great artist, but she’s got a spark that not a lot of people have.”

Heart Life Music will be published on Nov. 4 and is now available for preorder, wherever books are sold. Chesney will also kick off his 10-stop Heart Life Music book tour on Nov. 1 in Johnson City, Tennessee.

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