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…