Taylor Swift performs onstage during "Taylor Swift | The Eras Tour" at Allianz Parque on November 24, 2023 in Sao Paulo, Brazil./ Kenny Chesney performs at the 53rd Anniversary Nashville Songwriters Hall Of Fame Gala at Music City Center on October 11, 2023 in Nashville, Tennessee.
Buda Mendes/TAS23/Getty Images for TAS Rights Management/ Jason Kempin/Getty Images

How a Shocking Gift From Kenny Chesney Helped Taylor Swift 'Fuel Her Dreams'

Chesney's unexpected surprise came after Swift was rejected from joining him on tour.

In a new interview for her TIME Person of the Year cover story, Taylor Swift reveals that an early career surprise from country star Kenny Chesney gave her a life-changing opportunity. When she was 17, Swift was invited to open for one of Chesney's shows.

"This was going to change my career," the "Cruel Summer" singer shared. "I was so excited."

However, a couple weeks later Swift revealed that she came home to find her mother Andrea "weeping." She had to tell her daughter that because Chesney's tour was sponsored by a beer company, Swift was too young to join as the opening act. Though she was "devastated," a gift from Chesney on her 18th birthday more than made up for the missed opportunity.

At Swift's birthday party, Chesney's promoter handed her a note from the country star, reading "I'm sorry that you couldn't come on the tour, so I wanted to make it up to you."

Inside the note, Swift says there was a check for "more money than I'd ever seen in my life."

"I was able to pay my band bonuses. I was able to pay for my tour buses," she explained. "I was able to fuel my dreams."

Chesney's support highlights the importance of mentorship and generosity in the music industry, demonstrating how established artists can profoundly impact the careers of emerging talents. Meanwhile, Swift's recounting of this experience—which took place over a decade ago—underlines the significance of community and support in her journey to stardom.

Swift's history-making TIME cover is the latest in a long line of successes for the music icon. She's the first woman to appear twice on a Person of the Year cover since the franchise began in 1927. Among Swift's other 2023 wins is the massively successful "Taylor Swift: The Eras Tour" film, which helped make her a billionaire. She also continued re-recording her back catalog, releasing Speak Now (Taylor's Version) and 1989 (Taylor's Version), and celebrates several 2024 Grammy nominations, including one for Album of the Year for Midnights.

Taylor Swift's journey from a young talent to a global superstar shows just how far determination and skill can take you. Her story is a reminder to all that with hard work and a bit of luck, your "wildest dreams" really can come true.

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