One morning a few days ago, I received an odd email from someone I’d been writing back and forth with about the US Open: “Could we speak on your cell at 4pm? Something amazing may be possible.” That something, as it turned out, was a chance to hit—one on one—for 30 minutes with two-time US Open champion (and eight-time Grand Slam champion, Olympic gold medalist, Hall of Fame member, and all-around living legend) Andre Agassi the following morning at 7, in Arthur Ashe Stadium, at the USTA Billie Jean King National Tennis Center, a.k.a. the biggest prime-time stage at the Open—followed by breakfast and a chat in the Emirates Suite in Ashe.
Even thinking about it felt ridiculous: Though I’ve been playing tennis for decades, I’m also decades removed from my brief stint competing on the midwestern boys’ junior circuit. These days, I’m a supremely average once-a-week player perpetually on the verge of, you know, getting myself back in fighting form. I absolutely love to find the groove on a big-swing, big-finish crosscourt topspin forehand, I like playing a few sets against friends, but I loathe the notion of putting myself out there for even a local club tournament. Purely going on natural instinct, every fiber of my body told me to say no to this (admittedly mind-boggling) opportunity.
Emotionally, I realized I was going through some kind of inverse of the seven stages of grief, stuck on an odd kind of anger at this once-in-a-lifetime thing landing on my lap. Not one of the many actors I’ve interviewed ever asked me to step in front of the camera and read lines, or leap through a window as part of a big chase scene; zero of the musicians I’ve talked with over the years have asked me to stand in with them at Madison Square Garden and trade guitar solos or take over lead-vocal duties at their sound check—so why this?
Yet here was the offer: Play tennis, with one of the greatest to ever do so, in the largest tennis stadium in the world. I had 90 minutes to make up my mind.
The first thing I did was reach for a box filled with old photographs on a bookshelf in my living room, where I dug up a picture of Andre and me—in 1994—at a pre-Open Nike party at a restaurant near Gramercy Park. I have no idea what we talked about, and in any case I didn’t want to bother him or take up too much of his time, as he was there with Brooke Shields (they’d then been dating for about a year and would be married a few years later), and it seemed obvious that they adored each other’s company. No—I was just over the moon to even be there: a lifelong tennis nerd now, for the first time, around real tennis legends. (Aside from Andre I also met John McEnroe, who had arrived late, wearing a rumpled jean jacket and a scowl on his face, carrying an armful of vinyl records—a.k.a. exactly the Johnny Mac out of central casting that I wanted to see.)
It was only after brooding on this photo for a rather long time that it hit me: About two weeks after the picture was taken, Andre won the US Open for the first time—and the date proposed for my hitting session with him was exactly 30 years later.
The whole thing spooked me, so much so that I felt the only appropriate thing to do—particularly as my 90-minute window was swiftly closing—was to simply say yes to the whole damn thing. What was I going to tell my tennis-playing friends—that I’d been given a chance to play with Andre Agassi in Ashe Stadium… and said no?!
I arrived at the Open early and paced the utterly deserted grounds for a bit before heading up to meet Andre—100% ready to play in a head-to-toe purple-maroon ombré Nike kit topped off by a ski beanie—in the Emirates Suite. (Emirates Airline has been a major sponsor of the Open since 2012 and operates a massive quadruple suite—one of only two at the Open—on the mezzanine level, where they indulge their guests during the tournament with rare champagnes and caviar, a legendary sushi offering, and the sort of service you’ll recognize if you fly Emirates because the same cabin crew that works their A380s also work their suite. Suffice to say, then, that yeah: They can handle breakfast and coffee.)
As Andre and I sat down to chat, I asked him—he having done, no doubt, his fair share of these kind of hit-around-with-a-hack-player things over the years, mainly to benefit his Andre Agassi Foundation for Education, which focuses on underserved children in public schools—if anyone’s he’s hit with ever, you know, just kind of freaked out: overcome by emotion, a fainting spell, panic attack, that kind of thing. Andre simply laughed and told the story of an older man a few years ago, at a benefit in Lake Tahoe, who—perhaps not in peak form—lunged for an early ball and took a tumble, breaking his wrist on his non-hitting arm, but who insisted on playing through, as it were. A few balls later, another lunge, another tumble, this time accompanied by a loud cracking sound. The main clutched his calf and said that he’d snapped his Achilles tendon. “Are you sure?” Andre asked. “Yes,” replied the man. “I’m an orthopedic surgeon.” Rather than head to the emergency room that he so urgently needed, the man insisted on sitting down and watching Andre hit tennis balls.
As we chatted, it turned out that I didn’t know that much about Andre—even during his peak, when I saw him play again and again. Or if I did, the years between then and now had revised that history. For starters: He doesn’t really know his way around the Billie Jean King Center.
“My experience of the Open was mostly my car straight to the entrance, me going straight to the locker room, straight to the practice courts, straight to the match court—in 1986, my first year here, I played way out by some hamburger stand because I remember that smell. I lost to Jeremy Bates in four sets, first round—then straight back to the locker room, straight to the press room, straight to transportation, and back to the hotel,” he said. “So it’s been really cool to be back here and actually walk the grounds and get a feel for the place.”
The other thing I’d forgotten: Andre wasn’t always the hero here. His neon outfits and denim shorts and crazy hair—along with his outspokenness—weren’t nearly as welcome, at least within the relatively staid tennis community, then as they would be now, at a time when rebellion has long been packaged and marketed and sold.
“Oh my God,” Andre says when I bring this up. “In 1988 I was called a punk—I was destroying the game of tennis. I mean, what they call destroying it I called broadening the tent—but whatever. I just was being me, and I was always honest about how I felt about the game.”
And with that, it was time to head down to the court. As much as I’d tried to picture myself hitting inside that enormous building, though, there was one thing I hadn’t counted on to intimidate me and send a shiver up my spine: the walk through the hallway and the doors, and that final left-hand turn out into the stadium. Here’s where the roar of the crowds reverberates through the rafters as the players are introduced—and here’s where utter silence welcomed Andre and me to the court.
So…how’d it all go then?
Reader: It went about as well as you might expect. After a horrible start in which I was completely overawed by the occasion, I settled into something of a decent rhythm, and at least didn’t continually bring shame upon my family name. Andre seemed to know exactly what to do: When I started netting a few too many backhands, he delivered ready-made balls directly to the sweet spot for my topspin forehand. And just when I started to get a bit complacent or too accustomed to his beneficence, he thrilled me by ripping one of his world-famous two-handed backhands down the line at a speed I could only laugh at. He gave me invaluable advice about truly settling into my forehand with steady footwork instead of leaping for the ball. (I couldn’t help but confess that, in my real life, I didn’t jump when I hit forehands—it’s something I only do when playing with living legends.)
Most embarrassing (for me) and most impressive (for Andre), though, weren’t those trademarked two-handed backhands, nor his blistering forehands, but something else entirely—a wolf in sheep’s clothing, as it were. I could see them coming from across the court. Like anyone who’s played the game for a while, I can read—with my eyes, and my ears, and especially by noting what kind of path the ball is taking over the net toward me—what kind of shot my opponent is hitting. The most obvious options are a flat ball that bounces more or less where it should, a heavy topspin shot that’s going to nosedive on my side of the net and then kick up high and mighty, or a slice cut with underspin that skids and drastically slows down upon impact. So I saw Andre’s right hand go high behind him before chopping down low, sending the ball floating my way, slow and low, giving me plenty of time to get into place to dig it out with a wicked topspin cross-court backhand. Advantage, theoretically, me, right?
Here’s the thing: That ball never came anywhere near my racquet. I was swinging—through thin air—at the ball I was expecting, the ball virtually anyone I’ve ever played with delivered to me when swinging their racquet like this. What I actually got was magic—a ball that essentially died upon impact with the ground, a grass-court bounce on a hard court. I should have dropped my racquet and broken into applause, truly; instead, I burst out laughing again.
“What?!” Andre yelled from across the net. “It’s just a drop shot. Do you want me to hit it harder?”
After a half hour or so of this—the good, the bad, and the ugly of it all, the ecstacy (his shots) and the agony (my shots), I waved the white flag, and Andre and I walked to the side of the court, where two of the Emirates cabin crew were waiting for us with cold towels for our faces and ice water in crystal glasses perched on a tray.
After Andre dispensed some more advice (it seems that what I need to do in tennis more than anything, really, is to quiet down my body), I had one last question for him. It was about what he’d said up in the suite, about always being honest about how he felt about the game. It’s something Andre has a lot to say about in his autobiography, Open—truly not only one of the greatest books about tennis ever written, but one of the best, most open and honest memoirs I’ve ever read.
The central tension running throughout the book, starting on page one: For much of his career, Andre didn’t really want to play tennis. It was his dad’s dream for him, not his own, and that struggle caused all sorts of problems. Given all that, I asked Andre if the fact that he’s still playing tennis now—he mostly gave it up for a handful of years until a year or so ago—has any sort of special meaning. I wanted to know if the Andre of 1994 was the same guy as the Andre of now, or if he’s found a new way to be himself. Somehow, I expected an answer more glib, more assured, more of a sound bite than what I got. Clearly, I didn’t know the man.
Agassi, playing in a pickleball tournament in August 2024.
Photo: Getty Images
“I consider myself a searcher—you know what I mean?” Andre began. “Like an explorer, or somebody that just wants to understand, wants to learn. The greatest distance on Earth is the distance between a person’s mind and their heart. And we spend our life trying to bring them together. So I just see it as… not versions of myself… I see it as… No, I see me. I see me. And I’m searching, I’m exploring, I’m trying to understand, and I’m trying to, at the same time, be kind. But I didn’t always pull that off so well.
“It wasn’t until I got to number one in the world—which was my father’s foremost dream for me, or expectation of me—that I thought somehow things would make sense. Well, when they didn’t, I really spiraled. And after I spiraled, I recognized that choice is an illusion: We all think we choose, but we don’t choose where we’re born, what our strengths and weaknesses are, how they’re nurtured, how they’re not. But just because you don’t choose your life doesn’t mean that you can’t take ownership of it—doesn’t mean you can’t find your reason.
“I found my reason by helping children through education—children that really don’t have choice in their life and don’t have the luxury of bitching about being number one in the world. And once I got there, I took out a $40 million mortgage to build my own school. Now I had to play. I mean, we all care about a more comfortable life, but I was willing to put it on the line. But once I had my reason, this all looked different to me. This looked like the place I needed to be—the place that could give me what I really wanted. Not a trophy, but a platform—and an opportunity.”
