Breaking News: Kenny Chesney says he always knew Taylor Swift would become a superstar: “She had the eye of the tiger”…see more

Kenny Chesney has witnessed plenty of country talents emerge over his three-decade career, but he says he knew Taylor Swift was different from the very beginning.

In his upcoming book Heart Life Music (out Nov. 4), the 57-year-old country legend reflects on their first planned collaboration back in 2007. Swift, then a 17-year-old rising star, had been selected to open for Chesney on his Flip-Flop Summer Tour – until a beer company signed on as a sponsor, forcing her removal due to being underage.

Chesney made sure the setback didn’t stall her dreams. He cut Swift a personal check, and sent a handwritten note that read, “I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you.”

That gesture helped Swift pay her band bonuses, cover tour buses and – as she later told Time – “fuel my dreams.” Chesney says he saw the fire in her long before she began selling out stadiums worldwide.

“She had the eye of the tiger even as a teenager,” Chesney told PEOPLE. “She was really talented and really wanted it. I knew something special was going to happen there.”