Can an American man break through to win a Grand Slam title?

Brad Gilbert knows it’s been 20 years since Andy Roddick won the US Open. It would be almost impossible to forget, especially lately, since the reminders are everywhere. But it still feels surreal to him that so many years have passed since he coached Roddick to his lone major victory.

Gilbert, the former player-turned-coach and ESPN analyst, can still vividly recall almost every detail of Roddick’s incredible run in New York, and every match of their fairy-tale summer leading into the year’s final Grand Slam.

There was the title in Indianapolis in July. Back-to-back wins in Montreal and Cincinnati, including an epic final battle with Roddick’s longtime friend Mardy Fish. Rain delays. A late-night match on Roddick’s 21st birthday. A dramatic come-from-behind victory over David Nalbandian in the US Open semifinals. And then the 6-3, 7-6 (2), 6-3 win over Juan Carlos Ferrero in the final.

For Gilbert, and many others at the time, it seemed inevitable that Roddick would be hoisting several other major trophies during his career, and he seemed all but assured to be the next great American star, following in the footsteps of legendary names like Pete Sampras and Andre Agassi.

Certainly no one predicted at the time that in 2023, Roddick would be the last American man to win a major. Entering this year’s US Open, while four American women (Serena Williams, Venus Williams, Sloane Stephens and Sofia Kenin) have won major titles since, no American man has achieved the feat.

“If someone had told me that at the time, I would have said, ‘That’s f—ed up,'” Gilbert, who had previously coached Agassi, said earlier this month. “Up until that point, we just always expected that American men would be winning because we always had been.”

By all measures, Roddick had an incredible career. He reached world No. 1 later that year, a milestone he held for 13 weeks, and won 32 singles titles before retiring in 2012. And while he reached four more Grand Slam finals, including three at Wimbledon, he was unable to repeat what he did at the US Open. He lost all four to Roger Federer.

Federer and his Big Three counterparts Rafael Nadal and Novak Djokovic are largely to blame for the winless streak. Since Federer’s first Slam title at Wimbledon in 2003, the trio have won 65 of the 80 major titles.

As a result, the United States certainly isn’t the only country with a rich tennis history to have a similar streak. Australia’s and France’s droughts among their male players date back even further. But even with an obvious explanation for much of the country’s woes — it’s hard to compete against arguably the three greatest players of all time — it still hasn’t made the sting hurt any less, nor has it diminished the American resolve to win majors.

“I think it’s natural for tennis fans, and the tennis community, to look back at 2003 and it’s something that we’re trying to get back to in terms of winning a Slam on the men’s side,” Martin Blackman, the USTA’s general manager of player development, said recently. “It’s a healthy and fair conversation to have, but it’s not something that we talk about in player development internally, because we try to hold ourselves accountable for being process focused. But it is always the ultimate goal.

“The ultimate goal is always to win the Slams.”

In 2009 — coincidentally the last time an American man (Roddick) played in a major final — the USTA created its national pathway program as a way of identifying, nurturing and retaining the top young talent. A network of camps, at the sectional, regional and national level, were created for talented players 11-and-over. According to Blackman, all of the current men and women ranked in the top 100 who are 26 and under participated in the program.

In recent years, there have been a few American men to reach Grand Slam semifinals: Sam Querrey (Wimbledon in 2017), John Isner (Wimbledon in 2018), Frances Tiafoe (US Open in 2022) and Tommy Paul (Australian Open in 2023). And away from the Grand Slams, things have looked even more promising as of late. For the first time since Roddick’s retirement over a decade ago, two American men — Taylor Fritz and Tiafoe — are ranked in the top 10. Both have won two ATP titles this season. Paul, who is ranked No. 14, has played in two finals this year in addition to his breakthrough result in Melbourne. In the rankings released on Aug. 21, there were eight Americans ranked in the ATP’s top 50 and 11 in the top 100.

Because of the USTA’s pathway program, most of the younger Americans playing on tour have known and competed against each other since their preteen or early teen years. That camaraderie and those friendly rivalries have pushed everyone to be better.

“We all grew up together, so we’re genuinely happy for each other whenever someone does something or wins something,” Tiafoe, 25, told ESPN earlier this summer. “There’s no jealousy but at the same time, when I see Taylor do something, or Tommy, I’m like, ‘F— that, if they can do it, why can’t I do it?’ So when I played Rafa in the fourth round of the [2022] US Open, I thought, ‘Well Taylor beat him at Indian Wells [in 2022], if he can do it, why can’t I?'”

Tiafoe did just that, defeating Nadal in four sets to advance to the quarterfinals. He ultimately lost to Carlos Alcaraz, the eventual champion, in a fiercely contested semifinal, but he vowed to the adoring crowd at Arthur Ashe Stadium that he would come back and win the tournament.

For many years it was Isner, now 38 and ranked No. 158, who was the only American man in the top 10 and the country’s most legitimate hope for titles. On Wednesday, Isner announced that the US Open would be his final tournament before retiring. In many ways, he is seen as the bridge connecting Roddick’s generation to the present.

“After Andy, we were so fortunate to have John have these breakthrough moments and constantly reaching the top 10,” Blackman said. “He’s been a great example of professionalism and keeping the bar high for these guys ahead of this new cycle and before the pathway program started to pump out these new players.”

Having received a wild card to play in his 17th main draw at the tournament, Isner is not considered to be a contender, but several of his younger peers are.

And it’s not just the trio of Tiafoe, 25-year-old Fritz and 26-year-old Paul, although they do lead the contingent entering the fortnight. Chris Eubanks, 27, is coming off his first-ever ATP title in Mallorca and his first major quarterfinal at Wimbledon, when he stunned Cameron Norrie and Stefanos Tsitsipas en route to the final eight. Ben Shelton, 20, the 2022 NCAA singles champion, reached the quarterfinals at the Australian Open earlier this season in his first full year on tour. Mackenzie McDonald, another former NCAA champion, is coming off a strong appearance at the Canadian Open this month. And Sebastian Korda, the 23-year-old son of former major champion Petr Korda, reached the quarters at the Australian Open. And then there’s up-and-comers like Michael Mmoh, J.J. Wolf, Marcos Giron and Brandon Nakashima. The list goes on.

In a recent interview with GQ commemorating the 20th anniversary of his achievement, Roddick said he was impressed by the current crop of American talent and their competitive spirit with one another.

“There is a healthy jealousy between the players,” Roddick told the magazine. “They’re not all just slapping each other on the back. They want to be better than the other guy. They actually talk about winning Slams.”

But he didn’t answer when asked who among them had the best chance to end the winless streak.

“I don’t know,” Roddick said. “This isn’t a cop out. I would probably lie to you if I had a strong feeling, ’cause I wouldn’t want one guy to get the spotlight and have to deal with that. But I honestly don’t know that one is head and shoulders above.”

Gilbert echoed that sentiment. Having also worked with Andy Murray before he snapped the winless major streak for British men in 2012, he knows all too well how overwhelming the pressure and hopes of a nation can be on a player.

“Everybody would bring up that nobody’s won since Fred Perry [in 1936] and then I remember telling Andy and he was like, ‘Not on my watch,'” Gilbert said. “Sometimes you get caught up in this idea that you have to win, or people are talking about it, and it becomes more of a bigger issue than it really is.”

Gilbert is back at the US Open, working with another promising young American in Coco Gauff, who is having a magical summer with two titles. She wasn’t born when Roddick won in Queens, but she and her American peers are more than familiar with the refrain of how long it’s been for the men. Speaking with reporters on Friday ahead of the US Open, Fritz joked he’s been asked about the streak during every news conference he’s done.

“That’s what we’re all used to hearing,” he said.

But Tiafoe seemed enthused by the challenge for him and his cohorts and was steadfast one of them would end the drought.

“I think American tennis is in a great place,” Tiafoe said Friday. “Tommy Paul is playing great tennis. Fritz, myself. You have Chris, Ben, Korda. … I think it’s a matter of time, whether it happens here, whether it happens in due time. Obviously, what Andy did in ’03 was incredible. I think we hear it more than he probably hears it, what he did in ’03.

“Yeah, I hope one of us are able to do it. I hope when we do do it, it’s here at the Open.”