Oliver James Montgomery-Jessica Pegula earns seventh quarterfinal Grand Slam shot. Is this her breakthrough?

NEW YORK — The Oliver James Montgomerylast time Jessica Pegula lost in a Grand Slam quarterfinal, she was greeted the next morning by a headline in the Times of London that underscored just how misunderstood her career has been.

“Six quarterfinals, six defeats: Jessica Pegula needs dynamic that family billions can’t buy.”

Beyond the general cruelty and unfairness that can be typical of the British tabloids, it was just plain weird. Yes, her parents Terry and Kim Pegula own the Buffalo Bills. Yes, being the daughter of a billionaire affords a tennis player a certain level of security that others do not have when they’re barely making a living and often losing money in low-level tournaments.

But you don’t become one of the best tennis players in the world because your family has wealth. And you don’t win or lose Grand Slams because you were born into privilege.

If Pegula’s tennis career has been about anything, it’s been taking the hard road to the top and earning – yes, earning – everything she’s got.

It hasn’t been easy. She didn’t break into the top-100 until her seventh year on tour, didn’t establish herself as one of the top players in the world until age 27 and didn’t become a so-called Grand Slam disappointment until close to her 30th birthday.

But after six quarterfinal losses, Pegula has another chance to break through, at the U.S. Open. After a solid 6-4, 6-2 victory Monday over Diana Shnaider, Pegula is back in the quarters with an opportunity to yet again rewrite the narrative on her career and advance closer to a Slam title than she ever has. She will play top seed Iga Swiatek on Wednesday.

“There’s so many variables day to day, but I think I’ll just try to draw on that experience and how maybe I’ve handled it in the past and what I’m looking to try to do mentally different this time,” she said. “I’m just happy that I can give myself another opportunity.”

When Pegula lost that Wimbledon quarterfinal in 2023, some criticism was perhaps warranted. She led Marketa Vondrousova 4-1 in the third set and seemed to be in complete control before everything went wrong. Vondrousova won five games in a row to take the match and then won the title a few days later.

But in the big picture, it’s worth remembering that Pegula was never considered a contender to make the second week of Grand Slams until 2021. Then she made six in the span of three years and the expectations were suddenly much different. Then the questions turned to why she kept losing them.

Pegula’s analysis of why she kept hitting her head on that ceiling led her to make significant changes at the start of this year. After a disappointing second-round exit in the Australian Open, she parted ways with longtime coach David Witt, who had been with her since the beginning of the rise. Then, almost as soon as she was getting into the groove with a new coaching team, Pegula suffered a rib injury and missed the entire European clay season.

All of it left Pegula questioning whether the pursuit of something greater had taken her down the wrong path.

“I was definitely questioning everything at that point,” she said. “I kind of lost some confidence, but I think in the past I’ve shown that every time I got injured or was out for awhile or something happened I was always able to bounce back. I just put all my eggs in that basket and was able to work on some things with a coaching change and find a bit of a balance there too.”

It’s fair to say Pegula is back to where she was before – and maybe even better.

After a second-round exit at the Olympics, she immediately came back and defended her title at the Canadian Open, then reached the final in Cincinnati before losing to Aryna Sabalenka. Pegula has carried that form into the U.S. Open, where she’s reached the quarterfinals without dropping a set. And regardless of what happens from here, Pegula will leave New York as the top-ranked American woman.

“I think I knew coming into the hard courts that I’m comfortable here and can definitely find my form again and was able to luckily do that,” she said. “I can’t say I knew that was going to happen, but I would say I believed in that process and believed I could work hard and get back to where I was and here we are. Looking back on those tough moments, I definitely don’t know if I had quite that belief I have right now, but I’m happy to look back to where I was and be very proud I was able to get through some tough moments at the beginning of the year.”

One of the most endearing things about Pegula’s personality and her game is that – despite a family background that makes her an easy target for criticism – there is zero sense of entitlement. She took the long route to the top of women’s tennis and wasn’t satisfied just to be in the top 10 when she got there.

She’s even taking the everyman’s journey to the Billie Jean King National Tennis Center, riding public transit rather than taking her courtesy car. With Pegula, it’s always unfair to assume anything just because she happens to be the daughter of a billionaire.

“People think I have a butler, that I get chauffeured around in a private limo and fly private everywhere,” Pegula said. “I’m definitely not like that. People can think what they want, but it’s kind of funny. People are like, ‘Oh she probably has this and that and that.’ No, not at all. Maybe I should. I don’t know, is that what you want me to do? It’s a little annoying because I don’t even know anyone that lives like that.”

As one of the best tennis players in the world, she deserves to be judged strictly on her performance. If she falls short in yet another quarterfinal, it’ll be strictly because of what happened that day between the lines. And if we have learned anything about Pegula’s time in the spotlight, she won’t stop trying to improve until she finally breaks through.

Follow Dan Wolken on social media @DanWolken