Kenny Chesney reveals why he asked Taylor Swift to give back his money after cutting her from tour

Kenny Chesney reveals why he asked Taylor Swift to give back his money after cutting her from tour
Taylor Swift was supposed to be an opening act on Kenny Chesney's 2007 Flip Flop Summer Tour (Getty Images)

NEW YORK CITY, NEW YORK: Kenny Chesney recently opened up about an early decision he made in his career to cut Taylor Swift from his 2007 Flip Flop Summer Tour.

During an appearance on 'The Tonight Show with Jimmy Fallon', the 'American Kids' hitmaker shared details about how the young singer was originally slated to join him on tour but ultimately wasn’t included in the lineup.

Also Read: Furious Swifties roast Justin Baldoni for mentioning Taylor Swift in $400M lawsuit against Blake Lively



 

Kenny Chesney explains why he had to cut Taylor Swift from his 2007 Flip Flop Summer Tour

Taylor Swift, then only 17 years old, was set to open for Kenny Chesney during the summer tour. However, due to the sponsorship deal with a beer company, Chesney had to make the tough decision to remove her from the bill.

Despite the setback for Swift, Chesney made sure to compensate her for the lost opportunity, as per the Daily Mail.

Also Read: Taylor Swift’s response to Justin Baldoni’s accusation Blake Lively used her to 'pressure' him revealed

"I felt terrible because she was gonna lose some money. I wanted to make it up to her," Chesney explained. 

He went on to share how he gave Swift "a specific amount of money," adding, "'It was quite a bit of money.... because I wanted to make it up to her, right."

Also Read: Justin Baldoni claims Blake Lively used Taylor Swift and Ryan Reynolds to push him into changing script

ARLINGTON, VA - JUNE 06:  Kenny Chesney performs
Kenny Chesney performs 'This Land is Your Land' during a Remembrance and Celebration of the Life & Enduring Legacy of Robert F Kennedy at Arlington National Cemetery on June 6, 2018, in Arlington, Virginia (Leigh Vogel/Getty Images)

This gesture of generosity was something that Swift later recalled in her 2023 Time Person of the Year interview. Chesney’s decision to compensate the young artist was a testament to his early recognition of Swift's potential, even before her career skyrocketed.

Years later, the two musicians shared a moment of humor during the 2009 Country Music Association (CMA) Awards when they were both nominated for Entertainer of the Year. Chesney jokingly asked Swift for a refund after she won the award.

"I went up to her and gave her a big hug. I said, 'Congratulations, but give me my money back,'" Chesney recalled with a laugh. 

Kenny Chesney reflects on Taylor Swift's drive as he announces first-ever Las Vegas residency

Although Kenny Chesney wasn’t taking Taylor Swift on tour that year, he expressed his admiration for her work ethic and songwriting abilities. He knew then that she was destined for greatness, though no one could have predicted how global her success would become.

"I knew that she was very driven. I knew that she was a really good songwriter," the 'Summertime' singer shared, adding that no one was aware at the time "that a person really has the ability to touch the world like Taylor has."

NEW YORK, NY - NOVEMBER 08: Taylor Swift is seen on November 8, 2024 in New York City. (Photo by XNY/Star Max/GC Images)
Taylor Swift is seen on November 8, 2024, in New York City (XNY/Star Max/GC Images)

Chesney recently announced a residency at the Sphere in Las Vegas starting in May, a move that will mark his first residency in the city.

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

He explained that the venue will allow for a "shared moment" between him and his audience, although he admitted that he has not yet seen a show at the venue.

"We're already in rehearsals. We're going to be rehearsing. It's a lot to put together," the 56-year-old revealed. 

Tickets for the residency will go on sale next week, with the first shows kicking off over Memorial Day weekend.

More from MEAWW

Taylor Swift donates undisclosed amount for 'heartbreaking' Los Angeles wildfires: 'So much suffering'

Swifties praise Travis Kelce as he reveals how GF Taylor Swift comforts him greatly off the field

Share this article:  Kenny Chesney reveals why he asked Taylor Swift to give back his money after cutting her from tour