Kenny Chesney has been a supporter of Taylor Swift since her early days in the music business. 

In 2007, Swift, 35, who is reportedly in talks with officials in Shanghai over potential new performances, was supposed to an opening act on his Flip Flop Summer Tour, but when a beer company signed up to sponsor it, the She Thinks My Tractor’s Sєxy singer, 56, had to cut the Our Song artist from the bill. 

Chesney gave the then 17-year-old artist a generous severance to make up for the disappointment.

‘I felt terrible because she was gonna lose some money,’ he told Jimmy Fallon Thursday night on The Tonight Show. ‘I wanted to make it up to her.’

The Cruel Summer singer had referred that particular act of generosity in her Time 2023 Person of the Year interview.

‘I had to call Taylor and tell her she couldn’t go out on tour with me,’ the crooner explained, adding, ‘which now seems absurd, right?’ he said making a veiled reference to Swift’s multiple platinum records and recent $2 billion Eras tour payday. 

Kenny Chesney has been a supporter of Taylor Swift since her early days in the music business. In 2007, the country crooner had to cut the budding singer from his tour, due to a beer company sponsorship, but he gave her a generous severance

‘I said, “look, I feel terrible.” because she was going to lose some money, and I gave her a specific amount of money,’ he said. 

‘It was quite a bit of money…. because I wanted to make it up to her, right.’

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In  2009, ‘we were both nominated for CMA Entertainer of the Year,’ he explained, ‘that’s how H๏τ she was,’ he said, adding, ‘Well, she won.’

The Summertime singer said it was when the two met up backstage that he jokingly asked for a refund. 

‘I went up to her and gave her a big hug. I said, “Congratulations, but give me my money back.”‘

‘I knew she had something,’ Chesney said when Fallon asked him if he realized back then that Swift was destined for greatness. 

‘I knew that she was very driven. I knew that she was a really good songwriter,’ explaining that no one knew at the time ‘that a person really has the ability to touch the world like Taylor has.’

Chesney has signed on to begin a residency at the Sphere in Las Vegas beginning in May. 

Swift, now 35, had hinted at the story in her Time 2023  Person of the Year interview

Chesney elaborated on the story during an appearance on The Tonight Show Starring Jimmy Kimmel Thursday night. ‘I said, “look, I feel terrible,” because she was going to lose some money, and… It was quite a bit of money…. because I wanted to make it up to her, right’

In 2009, Swift won CMA Entertainer of the Year, breaking Chesney’s three year streak  (Pictured in Nashville in November 2009)

Chesney joked that when he met Swift backstage, ‘I went up to her and gave her a big hug. I said, ‘Congratulations, but give me my money back’   (Pictured in Nashville in March 2015)

Chesney said he Swift had ‘something. I knew that she was very driven. I knew that she was a really good songwriter,’ explaining that no one knew at the time ‘that a person really has the ability to touch the world like Taylor has’   (Pictured in London in August 2024)

Chesney revealed he was currently in rehearsals for his residency at the Sphere in Las Vegas beginning Memorial Day weekend.  Tickets were set to go on sale January 21

‘I’ve never done a residency in Vegas,’ the hitmaker said. ‘But this is such a unique different thing for me.’ 

The Billboard Music Award winner said he felt the venue would offer a ‘shared moment’ for him and the audience, although he has not yet seen a show there. 

‘We’re already in rehearsals. We’re going to be rehearsing. It’s a lot to put together.’

According to Cheney’s social media, tickets go on sale next week and the first shows begin over the Memorial Day weekend.