This year’s Us Open marks the 20th anniversary of Andy Roddick’s only major/Slam title. In 2003, Roddick won the US Open as a 21-year-old. He was the last American man to win a major title, although obviously, plenty of American women have picked up Slam titles since then (Serena, Venus, Sloane Stephens, Sonya Kenin, hell, even Lindsay Davenport returned and made some Slam finals post-maternity leave). But it’s a blight on American tennis that Roddick is the last American man to lift a big trophy in 20 years. It speaks volumes about the ostrich syndrome of the USTA and how the American tennis intelligentsia is far behind their European counterparts when it comes to training boys/men for the modern sport.

Still, Roddick is a mensch and he’s enjoyed his life after his 2012 retirement. He and his wife Brooklyn Decker have two children, multiple animals, multiple homes and multiple lucrative businesses. A-Rod appears on Tennis Channel and does recaps and commentary, and he’s insightful and funny and he still follows the men’s and women’s game closely. GQ decided to give Roddick a lengthy profile about his life and career and this was an excellent read, although it’s very long-winded. Some highlights:

He downplays the significance of his US Open title: He’s citing how many American women have won majors over the last two decades. “No one’s benefited more from one win,” he says. “Ever. Had an American man won the next year, you wouldn’t be here.”

His coach Brad Gilbert advised him to ditch his visor: He takes off his baseball hat to show his bald head. “If I would’ve known it would’ve ended like this,” he says, “I would’ve worn the visor a lot longer. I texted Brad and was like, ‘F–k you, man. You took away my best hair years.’”

His life changed after he won the US Open: “You’re 21 and you’re like, ‘This is awesome. I’m super famous.’ There’s a certain amount of like, ‘Oh, I hate being famous…’ But then you go to the restaurant where everyone is. Like, Shut up. You don’t actually hate it….[Lacoste] was the big pay day. I barely did anything that wasn’t required contractually ever again.”

His idols: “These guys—Connors, McEnroe, Chang, Courier, Andre, Pete. They were everything to me. And so it’s like, ‘It’s on you. Don’t f–k up what they built.’ If I couldn’t replace their tennis, I could somehow keep people in the building.”

He never wavered from the work: “The work was non-negotiable. I never viewed myself on the same level ability-wise as a Roger, so I always had this insecurity where if it got away from me…”

On Roger Federer: “I love Roger. 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, ‘F-ck Roger! To me it was like the sky. You’re not always looking at it, but you know it’s there.” For a diehard competitor like Roddick, what bigger challenge was there than trying to beat Federer and Nadal and Djokovic? Though as Roddick admits, “Maybe it went from a challenge to obsession at some point.”

How he hooked Brooklyn Decker: He had his attorney call her agent, which she thought was shady. “The only thing I will say in my defense,” Roddick says, “is I didn’t do it all the time. The shooting of the shot was a one-time thing.”

The heartbreaking loss to Federer in the 2009 Wimbledon final, 16-14 in the fifth, after which he made a charming speech on Centre Court: “It’s not about me in that moment. Pete doesn’t go anywhere. He doesn’t leave his living room. And he made the trip. You gotta have a little respect for history.” Still, he was distraught. “I was sad for me,. But I was sad for them [my team]. I was the only chance that Stephen Little had of winning Wimbledon. And I know he hurt, and the people there hurt, as much as I did in that moment. I remember this part f–ked me up during my Hall of Fame speech. I didn’t have kids while I was playing. And then I did by the time the Hall of Fame comes around. And I’m like, these grown-ass men gave up how many parts of their lives and children’s lives to try and win a tennis tournament? I knew the sacrifice that was being made, but you can know something and you can also not understand it fully until later.”

People started coming up to him after the 2009 Wimbledon: “Every person in the store was like, ‘Andy, man, tough one.’ As if we knew each other. And it was awesome. I’m like, Oh my god, this has been the water cooler conversation for like three days.”

Whether he would have traded his “everyman tennis player” vibe for the Wimbly title: “Probably. Because I would like to think that I could get over myself enough to build that bridge with the fans anyway. Had I won Wimbledon, I don’t think I would have one single regret. I’m not disappointed I didn’t win ten slams. I’m disappointed I didn’t win Wimbledon. You can have seven of ’em. I just wanted one.”

He likes the young crop of American men: “There is a healthy jealousy between the players. 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.” And who would he pick as the one to do it—the one to break American men’s 20-year curse? “I don’t know. 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.”

If he could change anything about his career, he wouldn’t have worked so hard. “I always operated out of, ‘If I’m not as talented as these guys, there’s no chance they can win the day as far as training or effort.’ If I could go back and change one thing in my career it would be to do less of that sh-t. I remember my last year on tour. I see this guy floating around and he’s like #25 in the world. He’s the happiest guy I’ve ever seen. And I’m just like…I just want one more look at the basket. I’ll do anything. And then there’s relief when you win, not out and out joy.”

The moniker “One Slam Wonder.” “I’m like, ‘F–ck, I won 32 times.’ I won two out of my last four or five tournaments. What would be a defining moment in someone’s career, it doesn’t matter if I win ten more of ’em. If it’s not a major, it would affect people’s perception zero.”

[From GQ]

There’s also some heartbreaking stuff about the death of his agent Ken Meyerson and his father. Basically, Roddick burned himself out with his intensity and grief, but his marriage, charity work and fatherhood brought him back to the land of the living. As for what he says about the new crop of young American guys – he’s not being diplomatic about it, he really doesn’t know. A lot of hopes are pinned to Taylor Fritz (a white guy, handsome, with an influencer girlfriend) meanwhile Frances Tiafoe and Tommy Paul both made Slam semifinals in the past year, and Paul seems to have #1 Carlos Alcaraz’s number. I hope Andy doesn’t dwell on the losses, but yeah… you can tell that the Wimbledon losses still hurt, especially 2009.

Photos courtesy of Cover Images, GQ.