In the pages of TIME’s 2023 Person of the Year feature on Taylor Swift, a touching tale was shared. During her chat with Sam Lansky, Swift reminisced about a pivotal moment in her career involving none other than Kenny Chesney.
At the tender age of 17, as she was just finding her footing in the music scene, Swift landed a golden opportunity—opening for the country legend Chesney. It was a dream gig, the kind that could shape a budding artist’s destiny. But alas, the excitement was cut short when a beer company swooped in to sponsor the tour, making her participation a no-go due to her underage status.
The news hit hard when her mom, Andrea, broke it to her. Fast forward to her 18th birthday bash, where a surprise awaited. Chesney’s promoter handed her a card from the man himself, expressing regret for the missed tour and a determination to make things right. Tucked with the note was a check, an amount that not only covered tour expenses but also fueled Swift’s dreams like never before.
Chesney, in a later revelation, shared the reasoning behind his gesture. He saw Swift not just as a musician but as a genuine “writer who had something to say.” To him, authenticity was key—living and expressing real experiences, steering clear of mere clichés.
Taking to Instagram after Swift’s interview, Chesney shared throwback photos and a personal caption. He reminisced about seeing that unmistakable spark in her eyes the first time she took the stage with them. He praised her journey, expressing delight at her Person of the Year recognition. The post concluded with a warm declaration of pride and love.
So, while 17-year-old Taylor Swift may have missed out on a big opportunity, Kenny Chesney never missed the magic in her. And now, she stands tall—happy, successful, and thriving.