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By Michelle McGahan
Contributing Entertainment Writer
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Kenny Chesney is looking back on his failed tour with Taylor Swift — and recalling the moment he made a bold demand of the pop superstar.
The country icon appeared on the Thursday, January 16, episode of The Tonight Show Starring Jimmy Fallon, where he spoke about the money he gifted Swift after the tour promoter canceled her opening slot on his early 2000s tour — a life-changing moment for the "Maroon" singer, who mentioned the milestone in her 2023 Time profile.
What exactly went down? As Chesney, now 56, explained it, Swift was 17 when she was booked to go on tour with the "She Thinks My Tractor's Sexy" artist, but the run "was sponsored by a beer company [that] ... came to us right before the tour started and said, 'We can't have a minor on the tour.'"
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While Chesney acknowledged that the decision "made sense," he had to be the one to "call Taylor personally and tell Taylor she can't come on tour with me, which now seems absurd, right?" the singer-songwriter quipped, referring to Swift's incredible success over the past two decades. (The Eras Tour broke multiple records and is now the highest-grossing tour of all-time.)
Revealing he felt "terrible" and noting that Swift was "going to lose some money," Chesney "gave her a specific amount of money."
While he didn't name the amount he gifted the 14-time Grammy winner, he acknowledged "It was quite a bit of money. Because I wanted to make it up to her."
Later on, however — after Swift toppled Chesney's reign as Entertainer of the Year at the CMA Awards — Chesney jokingly changed his mind.
Greeting her backstage, the "American Kids" singer "gave her a big hug and said, 'Give me my money back.'"
"That's a true story," he joked.
While Swift didn't mention that part of the story in Time, she remembered his monetary gift to her — which his tour promoter delivered to her at her 18th birthday celebration in 2007.
"It was for more money than I'd ever seen in my life," Swift recalled. "I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams."
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