A few years ago, Andy Roddick threw away nearly all of his trophies. “I thought, I don’t really need these,” he tells me. “Anyone who’s in our house kind of knows what I did.” We’re sitting on the screened-in porch of his lodge-like getaway in Cashiers, North Carolina, a remote village in the Blue Ridge Mountains. It’s a house that feels lived-in. Shoes can stay on. Coasters are never mentioned. One of the few prizes he’s kept, his runner-up platter from the 2006 US Open, lies on the living room coffee table, repurposed as a drink caddy, its surface stained with cocktail glass rings.
Roddick, soon to turn 41, is a big dude, six-two, bordering on burly. Dad-bod has been mostly kept at bay by daily workouts—usually Peloton. He’s wearing a T-shirt and shorts and a baseball hat from Sweetens Cove, the Tennessee golf course and whiskey brand he co-owns with a group that includes Peyton Manning. His wife, the model and actress Brooklyn Decker, is on her way, making the three-hour drive west from Charlotte, their primary home. Their kids, seven-year-old son Hank and five-year-old daughter Stevie, are at day camp. It’s just me and Roddick and the cat and Bob Costas the bulldog, who sniffs at our feet and waddles into the kitchen.
The trophy he won at the 2003 US Open is displayed even more inconspicuously than his runner-up platter: tucked into a corner of his Charlotte home office. As if to say, “That was just one phase of my life, and that phase is over.” And, yes, since 2012, when he abruptly announced his retirement on his 30th birthday, there have been other phases, other passions and pursuits. Fatherhood being the most obvious and important. His business ventures and philanthropy. His foray into TV commentating, at Fox Sports for a time and currently with the Tennis Channel. But that first phase can never truly end until another American man wins the US Open—or any other major. Until then, he exists to most people as “Andy Roddick: The Last to Do It.”
He downplays the significance of this status, citing how many American women have won majors over the past 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.”
Yet what’s always made Roddick so compelling isn’t the lone major he won but the others he did not—the cruel timing of his career. Shortly after winning the Open, Roddick reached number one in the world. He stayed there for 13 weeks. Then they came, one after another—Federer, Nadal, Djokovic. He would never reclaim the number one ranking or win another major, losing four finals to Federer, three at Wimbledon.
Roddick has rarely spoken in depth about how those defeats affected him, or what inspired his decision to retire so young, or the brutal toll the game can take on players’ mental health—a conversation other stars like Naomi Osaka and his friend Mardy Fish have begun to normalize. Even at his 2017 Hall of Fame induction ceremony, he spent most of his speech not self-reflecting but praising others who helped him along the way.
In fact, Roddick has stayed so quiet for so long that last spring, as the 20th anniversary of his famous win neared and I approached him with an interview request, Decker felt compelled to offer him some gentle advice: “It’s not the worst thing to remind people you’re alive.”
Stephen Little remembers where he was that September Sunday in 2003 when Andy Roddick’s life changed forever. How could he forget? It changed his life too. It was early evening when the veteran London cabbie returned to his suburban home in Muswell Hill and turned on the television. “You know that kid I picked up?” he told his wife. “He’s made it to the US Open final.”
Three months earlier, Little had been in the middle of his shift when he was hailed by a man he recognized: Brad Gilbert, Andre Agassi’s former coach and one of tennis’s great gurus. Little didn’t recognize his companion.
From his spot in the jump seat, Gilbert noticed the horse racing papers that Little kept in the car. “Oh, you like a bet?” Gilbert said. “You’ll want to have a bet on this young man here. ’Cause he’s gonna win Queens and Wimbledon.”
Gilbert first saw Andy Roddick play at the Los Angeles Forum in 2000, when he was a practice partner for the US Davis Cup team starring Agassi. “I couldn’t believe how big he was serving for 17,” Gilbert says of Roddick. “Even Andre was like, ‘Who is this kid just crushing the serve?’” Soon the media began to predict that Roddick would be the one to carry on the tradition of American men dominating grand slam tennis. “We heard it every press conference,” says James Blake, Roddick’s friend and Davis Cup teammate. “‘Are you the next Sampras? Is he the next Agassi? How are you guys going to fill those shoes?’ I took a chunk of it, but Andy took the real heat.” Even Sampras himself had anointed him, telling W in April 2003, “Andy is the future.”
A couple months later, having yet to make a major final and eager for progress, Roddick rang up Gilbert, who’d split with Agassi the year before. “Andy couldn’t have been any more different from Andre,” Gilbert says. “I could talk with Andre sometimes about strategy for three hours. Andy was about ten to twenty seconds and then it’s like Mission: Impossible. ‘This message will explode.’ He had so much testosterone.”
A few hours after Roddick’s call, Gilbert was on a plane to London, where Roddick was tuning up for the grass-court season. His first mandate concerned Roddick’s less-than-intimidating attire. “He was wearing this ridiculous orange visor,” Gilbert says. “I said, ‘Get a frickin’ proper hat, a trucker hat, anything. But you will never wear a visor in my presence.’”
As I recount this to Roddick, 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, ‘Fuck you, man. You took away my best hair years.’”
Despite their fashion differences, the two men quickly gelled. “Brad was a coach who’d seen everything I was about to experience,” says Roddick. “He had seen Agassi, the hype machine, the complicated personality. And the confidence with which he spoke about what was going to happen—I don’t know if he believed it, but it felt real.”
An emboldened Roddick won the Queen’s Club tournament and made the semis at Wimbledon, losing to Federer, who was en route to his first grand slam title. But Roddick would barely lose another match all summer, winning four hardcourt events prior to the US Open. Before that, though, he had to make it home.
As he was packing up at his hotel, he started to panic. He couldn’t find his passport. He wasn’t sure what to do. He didn’t know anyone in London who could help. Then he remembered Stephen Little. The cabbie had shared his number, in case they needed another ride. Roddick called Little—who had indeed thrown a fiver on Roddick to win Queen’s and Wimbledon—and explained his dilemma. It was the weekend of July 4th, and the embassy wouldn’t be open until Monday. Worried about Roddick spending a few days alone in London, Gilbert asked Little to look after him. And so the 20-year-old American and the 60-something Londoner ate meals together, went to museums, listened to music. “We made quite an odd couple walking around the streets,” Little recalls. At the airport, new passport secured, Roddick suggested the possibility of hiring him again next year.
At the US Open, Roddick continued to roll, dropping only one set before the semis. His opponent was Argentina’s David Nalbandian, who Roddick had dominated earlier that summer. This time wasn’t so easy. Roddick lost the first two sets, then saved a third-set match point. “Crowd gets really loud,” he recalls. “We were able to turn it.”
Crucially, he doesn’t say, “I was able to turn it.” He says, “We were able to turn it.” Tennis was never an individual sport for Roddick. He always saw himself as part of a team, almost like an F1 driver. “It kind of is the same,” he says. “It just doesn’t get treated the same. You see a pit crew. You don’t see the stuff we’re doing behind the scenes.”
That includes the work ATP trainer Doug Spreen did on him later that night. A series of blisters had formed on the ball of Roddick’s right foot. For an hour in Roddick’s Times Square hotel room, Spreen worked with a scalpel while Gilbert talked strategy for the final. Both Spreen’s treatment and Gilbert’s tactics were sound. Only once during his straight set rout of Spain’s Juan Carlos Ferrero was Roddick nervous: “I’m one point away from serving for it. He had a second serve. And I was thinking to myself, Just double-fault. And he double-faulted. I couldn’t breathe on the next switchover. I’m like, This is it. It’s yours now. I think I fired three or four aces. Just unconscious.”
After that final ace, as he joyously fell to one knee, he thought of his mom, Blanche. She and Roddick’s dad, Jerry, were there in the stadium, but he didn’t know where. His parents never sat in his box. Roddick recalls, “I was like, My mom’s somewhere and she’s thinking, All of those rides to practice…That has to be worth it to her now, if it wasn’t before.”
Pete Sampras had announced his retirement at that year’s Open, and Roddick had won it—as storybook as the torch-passing could be. Afterward he celebrated at a Manhattan restaurant with his family, friends, and longtime agent Ken Meyerson. “It was just this room full of appreciation,” says Roddick, “and we’re all just gonna get hammered cause God knows if this ever happens again.”
“I mean, we got hammered,” Gilbert says with a laugh. After dinner, some of the group headed to a club. “We took the trophy and were drinking out of it,” says Roddick. Then his eyes widen with a memory. “And [Jennifer] Capriati showed up out of nowhere! I was like”—he mimes handing the trophy to the three-time grand slam winner—“‘You know what to do with this. I haven’t done this before.’”
The party went into the early hours Monday, until Gilbert reminded Roddick he had to make the rounds on the morning shows. “He almost forgot about that,” says Gilbert.
Back in Muswell Hill, Stephen Little watched the entire match. “I said to my wife, ‘That’s the last I ever hear from him. He’s not gonna ring a London taxi driver now. He’s a US Open winner.’”
The first thing Roddick did after he finished his press the next morning was fly to Austin and buy a house. He’d lived there as a child, before the family relocated to Florida for its superior tennis training facilities, and always wanted to get back. A month or two after he moved in, his father came to visit. “He went nuts because my room was a mess,” Roddick recalls. “I go, ‘What is wrong? Can you just be okay with things?’”
Jerry Roddick had labored from a young age on the family’s Wisconsin dairy farm, served in the Army, and made a career as a Jiffy Lube franchisee. He instilled in Andy a devout work ethic, disdain for excuses, and intolerance for self-pity. But his temperament wasn’t always easy to deal with.
Such encounters would’ve been more frequent if not for Ken Meyerson, who signed Roddick when he was 17 and became a kind of buffer between the player and his father. “Ken ran a lot of interference that I didn’t even know about,” says Roddick. “My dad’s pissed about something? I never hear about it. Ken took a lot of bullets.”
Meyerson was an unusual agent for a sport so heavy on decorum. “South Beach mixed with sports agent,” says Roddick. “Slicked-back hair, perma-tan, sockless loafer—a disgusting lack of sock at any moment. He’s the prototypical agent who walks in: ‘Yo baby, what’s up?!’ But underneath the schtick, that fucking guy would’ve begged, borrowed, and stolen. He would be emotional about matches I lost that I was not emotional about.”
Meyerson didn’t have to do much begging after Roddick won the Open. The opportunities seemed endless. “You’re 21 and you’re like, ‘This is awesome. I’m super famous,’” Roddick says. “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.”
Here’s how famous Andy Roddick was at that time: He was in a “Got Milk?” ad. People posted fan fiction about him online. And he became (and remains) only the second tennis player (after Chris Evert) to host SNL. He was the paragon of an Early Aughts Bro: His favorite movie was American Pie, he loved Dave Matthews Band, and he shopped at Abercrombie & Fitch. He also looked like an Abercrombie model, and the typical magazine photo shoot featured him shirtless with a suggestive headline. (“Hot Roddick,” in the case of the April 2003 W feature.) Even SNL couldn’t resist such objectification, having him play a bare-chested gynecologist in one sketch.
“That was the culture then,” says Brooklyn Decker. “It was so wildly inappropriate, and we just accepted it. If you wanted to work and get to a place where you could call your shots you had to do things that were uncomfortable.”
Roddick hated photo shoots, but—with Meyerson’s tutelage—he understood they could help land big brand deals that would set him up for the rest of his career. Upon first turning pro, he had signed with Reebok, a company that had serious cachet. “It was Iverson and Jay-Z,” Roddick says. When his contract came up for renewal, in 2005, Roddick says he and Meyerson had “a handshake deal” with Reebok CEO Paul Fireman, with terms agreed upon. But the deadline for a signed contract kept getting extended. Roddick eventually found out that Reebok was in the process of being sold to Adidas; he surmises that the parent company didn’t want to sign any big new contracts. (At the time, Reebok’s chief marketing officer stated, “As our contract came to a close, and after carefully considering what is in the best interest of our business, Reebok has elected not to continue this partnership.”) Within a couple of weeks, Meyerson negotiated a new deal with Lacoste. “That was the big pay day,” Roddick says. “I barely did anything that wasn’t required contractually ever again.”
Lacoste’s tennis-specific heritage was especially appealing to Roddick, who considered it his mission to make the game more mainstream in the US, just as his idols once had. “These guys—Connors, McEnroe, Chang, Courier, Andre, Pete. They were everything to me. And so it’s like, ‘It’s on you. Don’t fuck up what they built.’ If I couldn’t replace their tennis, I could somehow keep people in the building.”
Roddick’s celebrity was turbocharged when he started dating singer and actress Mandy Moore, their nearly two-year relationship unfolding amid the early aughts gossip-site boom. In a 2004 story in Teen Vogue, Moore described how she and Roddick were often treated by the paparazzi: “He was in town and we were having dinner with friends, and some guy chased us clear out of the restaurant. We sat home for the rest of his stay.”
Jeff Lau, who met Roddick when they were kids in Austin and remains a close friend, recalls the frenzy of that time: “Entourage is fun to watch because I’ve been in the black car when girls were trying to pry their way in. There were some of the most beautiful girls I had ever seen who were throwing themselves at him. And he was unaffected.”
One difference between Roddick’s life and Entourage: His Turtle was a mid-60s London cabbie. Not only did Roddick continue to hire Stephen Little during grass court season; he rented a bigger house at Wimbledon so that Little could have a bedroom, got him a Wimbledon grounds pass, and hired his son, Paul, to work for him and Decker in America.
Such a down-to-earth mentality ensured Roddick was never at risk of losing himself to celebrity and all its temptations—that and the work ethic he inherited from his father. “The work was non-negotiable,” he says. “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…”
Roger. Sooner or later, our conversation always circles back to Roger.
“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.”
Lau is referring to Roddick’s infamous competitiveness. Everyone who knows Roddick has a story. Dean Goldfine, who succeeded Gilbert as Roddick’s coach in 2005, remembers their cutthroat Scrabble games. “He memorized, like, every three-letter word that had z in it,” Goldfine says. “It got to the point where you basically couldn’t beat him.” (Roddick clarifies: “Every two-letter word with potential for high point value: za, xi.”) Lance Hooton, Roddick’s former conditioning coach, remembers how they’d argue over picking All-NBA teams. “Four days later, we’d be in a taxi in Rome or somewhere,” says Hooton, “and he goes, ‘I can’t fucking believe you chose Tony Parker over Steve Nash.’” His friend Jen Hodge recalls a pickleball game on a trip to the Bahamas to celebrate Roddick’s 40th birthday. “Three hours later, I’ve got sweat pouring off me and blisters," she says. “I thought we’d go to a resort and have cocktails. Why did I think that?”
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.”
That point can be traced to when he sought out Hooton, who’d worked with Heisman winner Ricky Williams at the University of Texas. In Austin, during Roddick’s brief off-season, they’d hit it six days a week: track work, court drills, practice sets, weight room. Some days they’d even put on cleats and do football drills.
But one thing he did not mess with was his serve. Not since he first messed with it himself, back when he was 16, the day he got so pissed in practice that he reared back in this funky half-motion just trying to hit the ball as hard as he could and it went in. From then on, Roddick told every coach he worked with: the serve is off-limits.
“Even when I was playing,” says Sam Querrey, a Roddick contemporary who reached #11 in the world, “I’d peek my head out of the tunnel and watch him serve a handful of games. Maybe he’s going to hit 140 today. Every serve you’d look at the radar gun.” Hooton describes it as like a cannon being fired. Whenever he got lost on a huge complex of practice courts, Hooton could always tell where Roddick was playing by the sound of the boom.
But Roddick knew his serve alone was no longer enough. He saw the game changing. Court surfaces were slowing down. New racquet strings made it easier for players to generate more spin and hit passing shots. “I wanted it to be a Tyson fight,” Roddick says. “Basically walk up and punch you in the face. Now everyone was Holyfield. Everyone was moving. I didn’t need to be a mathematician to realize I was #1 then I was #2 then I was #3. I’m like, ‘That’s not the right trajectory. Can we reverse engineer me?’ And we tried hard.”
In 2006, he made yet another unconventional move, hiring a coach who had never coached before: his idol Jimmy Connors. “He had been gone 15 years,” Roddick says of the eight-time grand slam winner, who had all but disappeared from the tennis world in the mid-’90s. “He’s like a recluse, right? He didn’t know the players. But he knew technique, knew footwork. Jimmy, for that moment in time, was huge.”
When Roddick began working with Connors, his world ranking was #10. In the year and a half they were together, it got as high as #3. But a second slam remained elusive. Connors could not be reached for comment, but his investment in Roddick’s success is clear from a story Stephen Little tells. After Roddick lost in the 2007 Wimbledon quarterfinals, Little came across Connors near the locker rooms. “Jimmy was just sitting there and he was crying his eyes out. He was convinced he could make Andy win Wimbledon. He believed in him.”
About an hour into our conversation, Decker finally pulls into the driveway and enters the house. She has recently cut her hair into a bob, which makes her warm smile even more prominent as she shakes my hand. Roddick first fell for that smile in late 2006 when seeing Decker, a newly minted Sports Illustrated swimsuit model, host a football show on the magazine’s website. 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.”
Several months passed. Decker’s modeling career was taking off, but she was lonely living in New York with few friends. She Googled Roddick and watched his acerbic press conference from the recent 2007 Australian Open. She liked his humor. They talked on the phone for weeks before he came to New York for their first date. “We had breakfast the next morning,” she recalls. “We did not spend the night together.”
Soon she was taking a train to DC to watch him play. “I was nervous for everything but the playing,” Roddick says of that day. It wasn’t only the first time Decker saw him play, it was the first time she’d ever seen live tennis. “Tennis to me felt like such an off-limits, rich person sport. And so to see him breaking racquets, foul-mouthed, this renegade approach he would take sometimes—I always found it really funny, cause it seemed to shake up the rigid world that tennis was. I thought he was very sexy when I saw him play.”
“She used to like it when I yelled at umpires,” Roddick says.
Less than a year after they met, while Roddick was playing at Indian Wells, he proposed in their hotel room, struggling on his tendonitis-riddled knee, holding the ring in one hand and in the other a sprig of holly he’d snapped off a bush. Roddick was 25, Decker 20. As he recalls, “I went from, ‘I don’t think I’m gonna get in a serious relationship forever,’ and then we were engaged in, like, six months. And then we really got to know each other.”
They were married in April 2009. Both so focused on their careers and traveling constantly, they’d sometimes go two months without seeing each other. “If we hadn’t actually made that commitment,” Roddick reflects, “I don’t know that we get through that. I don’t know if she’d tell you the full truth cause she knows I don’t talk about stuff, but…”
But Decker does tell me. She too isn’t sure their relationship would’ve lasted without the conclusiveness of marriage—that and her husband’s ego. “It can get in the way of emotional evolution,” she says, “especially in men, but ego can also be a wonderful thing. With our relationship, I think that ego and insecurity about failing—and failing publicly—was very much a motivation to put our heads together and figure this out.”
Roddick admits he could be terrible to be around during tournaments, hyper-focused as he was. “And Wimbledon was when Andy’s nerves and the general tension was at its highest,” says Decker, “because that was that one that he really wanted.” But 2009 felt different. The mood was more relaxed. Roddick had hired John McEnroe’s former coach, Larry Stefanki, who helped him drop weight and improve his footwork. “I remember Brook and Larry just laughing every night over a glass of wine,” says Roddick. “It was a great vibe.”
The night before the final against Federer, Stefanki gave Roddick a pep talk in the backyard of their rental house. “You’ve got to allow yourself to free up and play. It’s not time to play careful. I know you’ve had your challenges. You don’t have to be better than him every day. You’re playing well enough to beat him.” As Roddick listened, he thought, He’s not giving the Gipper speech. He actually believes what he’s saying.
“It was so thrilling,” Decker says of her husband’s performance that day. “Because he was playing so beautifully.” Beautiful is a word more often associated with Federer’s game than Roddick’s, but he indeed played with a surpassing grace, holding serve the entire match, right up until the very last game. Federer once again prevailed, winning the fifth set 16-14 and thereby breaking Pete Sampras’s record of 14 grand slam titles. As the two men sat waiting for the trophy ceremony to start, the crowd chanted “Roger! Roger! Roger!” Once that died down, they did something unexpected, especially for the typically restrained Brits. “Roddick! Roddick! Roddick!”
Hat turned backward, the anguish plainly visible on his face, he stood up and raised his hand.
In his on-court interview, Roddick congratulated Federer; joked to Sampras, who was sitting in the Royal Box, about failing to “hold him off”; saluted the other former champions in attendance; and expressed his hope that one day his name would join theirs as a Wimbledon champion. He was, in that instant, a model of sportsmanship, the gesture among the most impressive things Roddick has ever done on a tennis court.
When I tell him this, he quickly dismisses the compliment: “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 don’t think that people got the true sense of how much his heart was ripped out that day,” says trainer Doug Spreen, who’d joined Roddick’s team full-time after the 2003 US Open. “He was back in the shower for twenty minutes, just sitting there with water running down him.” Spreen was sitting in the locker room when Federer took a seat next to him. “He said, ‘I feel really bad for you guys, and I feel really bad for Andy. I hope he gets this one time.’ I think Roger realized on that day that it wasn’t right to have a big celebration, and his words when he sat down next to me were…” Spreen pauses, crying. “He didn’t need to do that, and it was heartfelt.”
By the time Roddick emerged from the locker room, the All-England Club was nearly empty. Decker was in tears waiting for her husband. “He said, ‘Let’s go home,’” she recalls. ‘“We’ll talk about it when we get home.’ He was the one who was calming me down.”
Stephen Little picked up pizzas and beers and was back at the house with the rest of the team—including his son Paul, Spreen, and Stefanki—when Roddick and Decker arrived. “He looked exhausted,” says Paul Little. “But the first thing he said to us was sorry.” He then went to Stephen Little, who was crying, and gave him a big hug. Little cries again as he recalls the embrace. “It’s not a thing that grown men do,” he says.
“I was sad for me,” Roddick says. “But I was sad for them. 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.”
Roddick pauses. “I remember this part fucked 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.”
Before returning to Austin, he and Decker stopped for a few days in New York. Roddick popped into the Apple Store in SoHo and was surprised by how many people approached him. “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.”
Roddick had achieved what he’d long sought to do: he’d expanded the game’s audience. And in the effort and grace he displayed, he’d also changed his public image. “He said that he felt like he was sort of this brash, sharp-tongued tennis player,” says Decker, “and then overnight he turned into the everyman’s tennis player.”
But would he have traded that for the title?
“Probably,” Roddick says. “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.”
Roddick apologizes. He has to pause our conversation for a few minutes so he can Zoom into the Tennis Channel to provide some commentary. He leads me into the living room, where the network is playing on the TV above the fireplace. Just a few days ago Frances Tiafoe joined Taylor Fritz in the Top 10—the first time two Americans have been in that group in more than a decade. Roddick likes the chances of this new US generation.
“There is a healthy jealousy between the players,” he says. “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,” he says. “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.”
And what if one of them asked him to coach—to do what Connors did for him?
“The kids would have to be grown up to where if I left for two weeks they wouldn’t really notice I was gone,” he says. “So that’s ten years away. If there are still no winners, and there’s a guy you can help and maybe you break your own curse? That’d be interesting. I want someone to do it.”
It’s not like he doesn’t have enough to do without coaching. He recently cofounded yet another business, a virtual healthcare company called ViewFi. And of course there’s the Andy Roddick Foundation, which he started at 17, inspired by Agassi’s nonprofit. Since its inception, it’s helped thousands of lower-income Austin kids and their families, in recent years through after-school and summer programs. In the beginning the foundation merely funneled cash to organizations that do the on-the-ground work. But Roddick wanted to become more than a middleman. So he asked his friend Jeff Lau to move back to Austin and get involved.
After graduating from West Point and serving in Iraq—he learned of Roddick’s US Open win from a government-issued laptop at Camp Muleskinner in East Baghdad—Lau got a job on Wall Street and an MBA from Harvard Business School. “I warned Andy, ‘If I do this for you, I’m not fucking around. There are real opportunity costs for me to do this. You’re rich, you’re famous, you’ve got an amazing wife. You don’t have to do this. Are you sure?’”
Roddick was sure. So they reinvented it—right down to the office space, bypassing the fancy areas of Downtown Austin for a large plot on the east side of town where most of their work would be directed. “It sent a message that we were for real,” Lau says.
The headquarters remain there today, and Roddick is just as involved as ever. Lau’s question all those years ago seems just as pertinent now. He doesn’t have to do all this. He doesn’t have to be this busy. So why? When will it be enough?
“I drive a Chrysler Pacifica,” Roddick responds. “Enough happened a long time ago. I’m certainly not gonna sit around for the next twenty years. I need something to tick.”
That old obsessiveness. It remained even in the last few years of his career. Lance Hooton remembers a group workout that ended with 4x100-meter relay races: “Andy is one of the anchors. On the backstretch, the other anchor’s got a little bit of a lead. Andy’s closing. Five meters from the finish line he fucking dives. He hits and rolls. He’s missing probably half the skin on one of his legs and on his arms.”
Roddick admits his intensity could be a detriment. “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 shit.”
Even at the time, he wished he could feel less tortured. “I remember my last year on tour,” Roddick says. “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 prospect of joy was also diminished by loss. In October 2011, Ken Meyerson died of a heart attack in his sleep at the age of 48. Two weeks later Roddick found himself in the locker room at a tournament in Switzerland having the biggest emotional breakdown of his career. “He would’ve been here at this shitty-ass tournament at the end of the year when no other agents come,” Roddick remembers. “He would’ve been here doing something ridiculous. And I just lost it. I was physically incapable of keeping my body still.”
Was that why he retired the following year?
“I don’t know,” Roddick says. “He probably took some of my love of the game with him.”
He also felt a certain futility, a needling awareness of the cruel moniker “One Slam Wonder.” “I’m like, ‘Fuck, I won 32 times,’” Roddick says. “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.”
Decker recalls that the last two years of Roddick’s career were different. “He was not as happy playing,” she says. “He became significantly less patient with his injuries. He was irritable. And I naively thought, I married this man and now he’s changing. What’s going on here?” He was still young, but often he was acting like an old man. What happened to the guy who’d snapped off that sprig of holly? Where was that Andy?
“And when he retired,” Decker says, with a snap of her fingers, “it was like a light switched on in him. And he became the person who I knew and fell in love with. And after some time I realized, Oh, this is a man who was suffering and really grappling with the end of his career. And the end of that identity.”
By the time Roddick finishes his Tennis Channel duties, Decker has left to pick up the kids. We head back to the porch, a light rain pattering the trees.
He hadn’t planned it, that morning of his 30th birthday in August 2012, heading into the second round of the US Open. Decker had left their Manhattan hotel for work. Roddick texted her to come back. He told her he was going to retire and announce it that day. “Are you sure this is what you want to do?” asked Decker, though she knew he was sure as soon as he said it. “I went to bed an active tennis player,” Roddick says, “and when I woke up I was gonna retire.”
Even for Roddick’s last match, in the fourth round, his parents didn’t sit in his box. But for the first time at any US Open, he knew where they were. So he was able to look at them during his post-match speech, his voice breaking as he thanked them for giving him every opportunity.
“One final thought,” said Roddick. “I’d like to say thank you to someone who’s not with us anymore.” He tilted his head back and looked out of Arthur Ashe Stadium. “To Ken Meyerson, thank you for everything. I love you.”
Two years later Jerry Roddick died of a heart attack, just a couple weeks before Andy turned 32.
“Andy’s endured, for someone his age, a pretty significant level of loss and death,” says Decker. “These big losses he’s had—mentor, father—that’s very much a part of who he is."
When I ask him about these losses, Roddick deflects with a quip. “I guess if there was a joke to be made,” he says, “it’s after 13 years of their relationship my dad and Ken both had heart attacks.” But then he grows somber. “I hope Ken knows that I was loyal to him as he was to me,” he says. “I hope he knows that I wouldn’t have left no matter what. I don’t know if I expressed that. The part that bothers me the most is not knowing how our relationship would’ve manifested. That’s the part I hate.”
He has a better sense for how his relationship with his dad would’ve turned out. “I think I would’ve been an easier adult to deal with than a young adult to deal with,” Roddick says. “And I think he would’ve been a better grandfather to deal with than father.” He pauses. “Maybe I just want it to be that way. I don’t know…I regret not being able to have conversations with my father after I was a father.”
Now that he has kids, Roddick has a better appreciation of his dad’s parenting style. “It wasn’t a control thing,” he says, “it was a worry thing. He was just so protective. I don’t agree with his methods, but I now understand them.”
Yet no matter how much we might try to differentiate ourselves from our parents, we are always, inescapably, their children. I remember a story his friend Jen Hodge told me about Roddick’s son learning to ride a bike: “Hank said to him, ‘Dad, I just need to work harder and I’ll be better.’ Andy was like, ‘Oh my god, no one has ever spoken words that relate to me more.’”
I’m tempted to ask Roddick about this anecdote but refrain. The children are home and eager to see their father. On my way out, they politely shake my hand. Hank tells me his favorite basketball team is the Hornets. Stevie shows off her Croc charms. Decker hugs me goodbye.
Andy Roddick leaves his family standing in the soft glow of the doorway and walks me to my car in the drizzling rain. “Thanks for coming,” he says as dusk creeps across the sky. “I know it’s not an easy place to get to.”
Sean Manning is a vice president and executive editor at Simon & Schuster. This is his first story for GQ.