The Last to Do It. Andy Roddick has carried that moniker since he won the 2003 U.S. Open at just 21 years old. In the last 20 years, no other American man has won any of the four major tournaments in tennis. Roddick was the face of U.S. tennis for a decade, but his career ran up against the sport’s Big Three, a trio of all-time greats: Roger Federer, Rafael Nadal, and Novak Djokovic collectively won all but a handful of major tournaments in the 2000s and 2010s.

Reporting for GQ, Sean Manning reveals that the long-retired tennis player—to quote a close friend of his—wouldn’t have had it any other way. In his first piece for the magazine, Manning tracks Roddick’s evolution from teenage prodigy to “Early Aughts Bro” to frustrated one-hit wonder, and finally to seemingly content husband and dad. Add this to the list of great tennis profiles.

“I love Roger,” Roddick says. “I do. I love him as a human being.” But after so many losses to Federer—21 in 24 matches—Roddick admits that he developed an insecurity. “I didn’t show up at the track every morning like, ‘Fuck Roger!’” he says. “To me it was like the sky. You’re not always looking at it, but you know it’s there.”

I had long seen this as the central drama of Roddick’s story—the torment of being so thwarted by timing and circumstance. You’re Christopher Marlowe, you’re feeling pretty good, and then here comes this Shakespeare guy. “Surely he would have had at least five majors if he played a few years earlier,” says Jim Courier.

But Roddick’s friend Jeff Lau sees it differently: “It’s sad that people view him as being at the wrong time in the tennis cycle. He wouldn’t have had it any other way.”