Long before fame, Taylor Swift sought the opportunity to perform for an audience whenever it presented itself. She entered karaoke competitions, became involved with musical theater, and sang the national anthem at sporting events. By the age of 12, she had the opportunity to sing the anthem at the US Open. A producer didn’t think she’d be a good fit, though. Years later, he still views this as the biggest mistake of his career.

Taylor Swift lost her chance to perform the national anthem at the US Open

Swift has known she wanted to be a singer since an early age and did all she could to get in front of a live audience.

“When I was 11 years old, it occurred to me that the national anthem was the best way to get in front of a large group of people if you don’t have a record deal,” Swift said, per WHYY. “So I started singing the national anthem anywhere I possibly could.”

Taylor Swift | Jason Squires/WireImage

When she was 12, she had the opportunity to sing the national anthem at the US Open. Ultimately, she didn’t perform that year because a producer thought she wouldn’t be the right fit. She was a young country artist, and she would have been performing in New York. Upon reflection, however, this was one of the producer’s biggest regrets.

“Her father asked us if we’d put her on Arthur Ashe Kids’ Day, and we said: ‘She’s just taking off, she’s really country, we don’t think that would play in New York,’” producer Michael Fiur said on the Served podcast (via Express). “I do not share this publicly very often. Worst decision I ever made.”

Taylor Swift said she tried to perform at every opportunity

While Swift had some massive opportunities as a young singer, she said she was happy singing karaoke at that age.

“Singing country music on that karaoke machine was my favorite thing in the world,” she told Rolling Stone in 2009.

She entered competitions and continued joining them until she won.

“I sang every single week for a year and a half until I won,” she said.

She revealed another early career disappointment

Not long after her thwarted attempt at the national anthem, Swift booked a job opening for Kenny Chesney on tour.

“This was going to change my career,” she told Time in 2023. “I was so excited.”

It was a major opportunity, but it soon fell apart because of her age. A beer company sponsored the tour, and they could have an underage Swift performing.

Kenny Chesney and Taylor Swift | Rick Diamond/WireImage

“[My mom] was weeping,” Swift said. “Her head was in her hands as if there had been a family emergency.”

It was one of her biggest career disappointments at that point in her life.

“I was devastated,” she said.

Chesney felt so bad that he paid her for the tour even though she couldn’t perform.