Taylor Swift Shares Her Kenny Chesney Heartbreak And How He Helped Launch Her Career (2024)

Taylor Swift was 17 years old when she came home to find her mother sobbing on the front steps of their home. She was crying so hard that Swift thought a family emergency had occurred.

There hadn’t - just something that could have negatively impacted Swift’s career. Swift told TIME she had been booked in the opening slot of Kenny Chester’s summer tour - the most significant opportunity of her life at that time.

“This was going to change my career,” she said. “I was so excited.”

Her mother had just found out that Chesney’s tour was going to be sponsored by a beer company, which meant that Swift could no longer be on the bill due to her age.

“I was devastated,” Swift said.

Swift turned 18 a few months later in December, and Chesney sent an unexpected gift to her party. The singer saw Chesney’s promoter among her partygoers, and he handed her a card.

Swift remembers the card said: “I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you.”

He sent a Happy Birthday check with the note.

“It was for more money than I’d ever seen in my life,” Swift said. “I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams.”

Swift was just named TIME magazine’s 2023 Person of the Year. The magazine reports that she has built a business worth an estimated over $1 billion.

Taylor Swift Shares Her Kenny Chesney Heartbreak And How He Helped Launch Her Career (2024)
Top Articles
Latest Posts
Article information

Author: Corie Satterfield

Last Updated:

Views: 5876

Rating: 4.1 / 5 (62 voted)

Reviews: 93% of readers found this page helpful

Author information

Name: Corie Satterfield

Birthday: 1992-08-19

Address: 850 Benjamin Bridge, Dickinsonchester, CO 68572-0542

Phone: +26813599986666

Job: Sales Manager

Hobby: Table tennis, Soapmaking, Flower arranging, amateur radio, Rock climbing, scrapbook, Horseback riding

Introduction: My name is Corie Satterfield, I am a fancy, perfect, spotless, quaint, fantastic, funny, lucky person who loves writing and wants to share my knowledge and understanding with you.