Scoring a VIP pass to a Taylor Swift concert is akin to catching a falling star since it requires celestial alignment. In fact, balling on Swift, given her stratospheric superstardom, is as good as a fool’s errand. Yet, Kenny Chesney recently spilled the beans on a shocking reason that led him to pull the plug on a commitment to the Eras Tour songstress. 

As countries clamor to land Swift’s tour, hoping to experience an economic boom like the ones she sparked throughout her Eras Tour, Chesney’s cancelation has left many curious—what secrets lie behind his decision to leave Swift hanging?

During a recent appearance on The Tonight Show starring Jimmy Fallon, Kenny Chesney reflected on when he had to drop Taylor Swift from his tour early on. The 56-year-old booked the ‘Karma’ singer for one of his tour shows and later revoked the invitation because the pop sensation was a minor back in the day. The tour she was set to do with Chesney in 2007 had a beer company sponsor, and they reportedly objected because Swift was only 17.

“I had to call Taylor personally and tell her she couldn’t go on tour with me,” Chesney recalled, pointing out that it may seem a little “absurd” now. Although Chesney monetarily compensated for the missed chance, he still felt awful. Later that year, Swift and Chesney were nominated for CMA Entertainer of the Year, and the 35-year-old bagged it home. Chesney may have quipped about a refund, but in reality, all he had to offer was a hearty dose of hospitality—a warm hug and a side of pride.

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Taylor Swift, herself, recounted this incident after being declared the Time’s Person of the Year in 2023 while giving a shout-out to Kenny Chesney for his generosity.

In the 2023 Time Person of the Year cover story, Taylor Swift wore her heart on her sleeves for Kenny Chesney, reminiscing about the 2007 canceled tour. She recalled a note Chesney sent with the cancelation news that left her mother “weeping.” “I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you,” the note read, including a check, which Swift added was way more money than she had ever seen in her life before.

Talking to the USA Today in March last year, Chesney revealed having left her a “thank you” note for the shout-out. Swift revealed in 2023 that she could pay for the tour buses, and her team with the money, and Chesney was swelling with pride in learning “what she did with that and the person she is now.” In the end, the tour’s cancelation was less a heartbreaker and more a career-maker that set the stage for her meteoric rise to fame.

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