Kenny Chesney recalls cutting Taylor Swift from his tour and jokingly asking for his money back

Kenny Chesney has long supported rising talent, and one of his most notable gestures involved Taylor Swift. However, an act of generosity during her early career turned into a lighthearted joke years later when Chesney asked Swift to return the severance he paid her after removing her from his 2007 Flip Flop Summer Tour.

During an interview on The Tonight Show Starring Jimmy Fallon, Chesney revealed that Swift was originally scheduled to open for his tour. Unfortunately, a sponsorship deal with a beer company conflicted with Swift's young audience, forcing him to cut her from the lineup.

Why Kenny Chesney removed Taylor Swift from his tour

"I felt terrible because she was gonna lose some money," Chesney admitted. To make up for it, he gave the aspiring artist a generous severance package. "It was quite a bit of money... because I wanted to make it up to her."

Chesney jokingly asked for a refund

Fast forward to 2009, Swift had become a superstar, even beating Chesney for CMA Entertainer of the Year. When they met backstage at the event, Chesney congratulated her with a hug and joked, "Congratulations, but give me my money back."

Reflecting on Swift's success, Chesney told Fallon, "I knew she was driven. I knew she was a really good songwriter. But nobody could've known she'd touch the world like she has."

Chesney prepares for a Las Vegas residency

Chesney, now a country legend himself, is set to begin a residency at the Sphere in Las Vegas starting in May. "I've never done a residency in Vegas, but this is such a unique, different thing for me," he said.

The residency will kick off over Memorial Day weekend, with tickets going on sale next week. Chesney promised fans an immersive experience, describing the Sphere as a venue that fosters "shared moments" between artist and audience.