The year: 2001. The location: US Open. The artist: Taylor Swift.

Before Taylor Swift became Taylor Swift, billionaire singer songwriter and businesswoman, she was pre-teen country artist Taylor Swift, singing the national anthem at the US Open. The following year, she was brought back again, this time to sing “America the Beautiful” at just 13 years old.

But looking back on what would have been her third straight year performing in Flushing, US Open veteran entertainment producer Michael Fiur revealed a hard truth on this week's episode of Served with Andy Roddick. Fiur’s resume as an executive producer includes 29 Super Bowls, five Super Bowl halftime shows and 28—and counting—consecutive US Opens. But he revealed a professional decision to Roddick that’s difficult to comprehend in hindsight.

“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,' and I do not share this publicly very often,” Fiur said. “Worst decision I ever made.”

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Although having Swift at AAKD would have been legendary for Flushing Meadows, Roddick and Fiur agree that the Opening Night guest list speaks for itself over the years: Aretha Franklin, Kelly Clarkson, Gloria Estefan, Whitney Houston, Rob Thomas and other Grammy-winning stars.

“How the hell do you book Whitney Houston night one of Arthur Ashe Stadium?” Roddick said before fan-girling over previous US Open performer Phil Collins.

Fiur also confirmed rumors that Justin Bieber’s first TV appearance in 2009 was at the US Open—where, at 14 years old, he was interviewing Will Ferrell in the player’s lounge.

“It is pure gold,” Fiur said on Bieber. “Justin had not been back until last year for the first time, and he was like, ‘Wow, this all looks so different, bigger actually.’”

Taylor Swift returned to the US Open this year as a fan, not a performer.

Taylor Swift returned to the US Open this year as a fan, not a performer. 

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The two discuss how much the US Open experience has evolved over the last several years, especially since the first ever Pride Night in 2019.

“For a long time, the US Open didn’t have a platform for diversity inclusion beyond Arthur Ashe Kids Day and Arthur’s name, but was really proud in 2019 to have created the first Open Pride event, which was a conversation held during the first fan week,” Fiur said. “As the diversity, equity and inclusion department has grown over the last several years, it’s grown to put the Open Pride event in the main draw of the Open to create an HBCU event, also Latin, also AAPI.

"To see this now become part of the fabric of the Open, for me personally, to have seen this growth and this change and the organization get behind it, makes me very proud to be associated with an organization that has these beliefs and shares my beliefs.”

Unlike Taylor Swift, Justin Bieber performed on Arthur Ashe Kids Day (2009).

Unlike Taylor Swift, Justin Bieber performed on Arthur Ashe Kids Day (2009).

Roddick adds, from a player’s point of view, that recognizing groups of people and their cultures came naturally, and that it’s about time there’s effort to showcase it during an event as massive as the US Open.

“The gift of my lifetime is traveling at such a young age, in the tennis world, where you are traveling to different cultures, you’re around a million different people,” he said. “Someone being gay or Black or anything else was just so normal in tennis, and I’m glad it’s being represented by the US Open. What better place in the shadow of the celebration of sport to really celebrate these things?”

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The balancing act of diversity and inclusion, entertainment, and memorability all came back to one commonality: tennis.

“For years, I had the mentality that entertainment was everything and entertainment was paramount,” Fiur said. “Over time, tournament directors tried to drum into me that tennis does come first, so I really integrated that into my thinking over the years and allowed room for tennis amongst the entertainment.”

This year’s US Open was no different. On Opening Night, Alicia Keys performed her signature song from her Broadway Musical Hell’s Kitchen, “Kaleidoscope,” which followed a record-breaking Opening Day attendance record—and ultimately contributed to the US Open welcoming one million fans for the first time.

“I think the growth coming out of Covid has been exponential,” Fiur said. “I think people desire to experience live events, be around people again, so the last couple of years have been off the charts.”