<p id=”par-1_61″>In the early days of her career, Kenny Chesney hired <a href=”https://www.cheatsheet.com/tag/taylor-swift/?swcfpc=1″>Taylor Swift</a> to open for him on <a href=”https://www.cheatsheet.com/music/”>tour</a>. The opportunity was a thrill for her; she was still a teenager, and the job would expose her to a much larger audience. Unfortunately, she wasn’t able to tour with him in the end. Chesney spoke about why he had to replace Swift.</p>
<h2 class=”wp-block-heading” id=”h-kenny-chesney-said-he-felt-terrible-about-having-to-fire-taylor-swift”>Kenny Chesney said he felt terrible about having to fire Taylor Swift</h2>
<p id=”par-2_48″>When Swift was 17, Chesney hired her to <a href=”https://www.cheatsheet.com/entertainment/taylor-swift-opens-up-about-leaving-country-music-behind.html/”>open for him on tour</a>. She felt this was a life-changing opportunity, but it was taken away from her at the last moment. A beer company sponsored the tour and informed Chesney that he couldn’t bring a minor with him.</p>
<p id=”par-3_48″>“They came to us right before the tour started and said, ‘We can’t have a minor on the tour,’” Chesney said, per <a href=”https://www.billboard.com/music/country/kenny-chesney-paid-taylor-swift-tour-money-buffett-sphere-residency-tonight-show-1235877982/” target=”_blank” rel=”noreferrer noopener”>Billboard</a>. “Which made sense. But I had to call Taylor personally and tell her she couldn’t go on tour with me, which now seems absurd, right?”</p>
<figure class=”wp-block-image size-full” id=”emb-1″><img decoding=”async” src=”https://www.cheatsheet.com/wp-content/uploads/2025/03/Taylor-Swift-Kenny-Chesney-1.webp?strip=all&quality=80″ alt=”Taylor Swift wears a blue dress and stands with her arm on Kenny Chesney’s shoulder. He plays guitar and sings into a microphone.” class=”wp-image-3784485″><figcaption class=”wp-element-caption”>Taylor Swift and Kenny Chesney | Frederick Breedon IV/WireImage</figcaption></figure>
<p id=”par-4_10″>The news came as a huge blow to Swift’s family.</p>
<p id=”par-5_21″>“[My mom] was weeping,” Swift told <a href=”https://time.com/6342806/person-of-the-year-2023-taylor-swift/” target=”_blank” rel=”noreferrer noopener”>Time</a>. “Her head was in her hands as if there had been a family emergency.” </p>
<h2 class=”wp-block-heading” id=”h-kenny-chesney-paid-taylor-swift-to-make-up-for-her-disappointment-nbsp”>Kenny Chesney paid Taylor Swift to make up for her disappointment </h2>
<p id=”par-6_20″>Swift said she was “devastated” by the loss of the opportunity. Chesney tried to make it up to her, though.</p>
<p id=”par-7_38″>“It was for more money than I’d ever seen in my life,” Swift said. “I was able to <a href=”https://www.cheatsheet.com/entertainment/taylor-swift-fed-eras-tour-team-worlds-most-prized-ham-outrageously-priced-dishes.html/”>pay my band bonuses</a>. I was able to pay for my tour buses. I was able to fuel my dreams.”</p>
<p id=”par-8_17″>While Chesney didn’t share how much money he gave her, he confirmed that it was a lot.</p>
<p id=”par-9_24″>“I gave her a specific amount of money… it was quite a bit of money, because I wanted to make it up to her.”</p>
<h2 class=”wp-block-heading” id=”h-he-admitted-that-he-later-asked-for-his-money-back”>He admitted that he later asked for his money back</h2>
<p id=”par-10_36″>Not long after this, Swift and Chesney were both nominated for Entertainer of the Year <a href=”https://www.cheatsheet.com/entertainment/taylor-swift-didnt-worry-losing-fans-swapped-country-pop.html/”>at the CMAs</a>. Swift ended up taking home the award. Chesney congratulated her afterward. He jokingly asked for his money back.</p>
<figure class=”wp-block-image size-full” id=”emb-2″><img decoding=”async” src=”https://www.cheatsheet.com/wp-content/uploads/2025/03/Swift-Chesney-1.webp?strip=all&quality=80″ alt=”Kenny Chesney wears a tank top and cowboy hat. He is on stage with Taylor Swift, who wears a gray shirt and skirt. She lifts one arm in the air.” class=”wp-image-3784489″><figcaption class=”wp-element-caption”>Kenny Chesney and Taylor Swift | Rick Diamond/Getty Images for Kenny Chesney</figcaption></figure>
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<p id=”par-11_26″>“Well, she won,” Chesney said. “So, backstage, I went up to her and gave her a big hug. I said ‘Congratulations, but gimme my money back.’”</p>