Andy Roddick on Winning the U.S. Open, Losing to Federer, and Why He Threw Away

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 U.S. 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 tee 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 U.S. 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 U.S. 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 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.”

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…