Jannik Sinner's Grass Roots
As Jannik Sinner achieves Wimbledon immortality, a look back at his legendary first steps onto these grass courts.
WIMBLEDON, England — I remember the first two times I saw Jannik Sinner vividly.
The first was in Rome in 2019. As soon as his face popped onto my monitor in the Foro Italico press room, I snapped several photos with my phone, eager to show others how a wee ginger child had somehow been given a wildcard into this tournament.
Sinner was 17 but looked at least five years younger; like a young Jodie Foster, I couldn’t help but think.
But then when Sinner rose from his chair and began hitting the ball, I was even more floored by what I saw.
I soon left my desk to go into Campo Centrale to witness him for myself: this wisp of a boy was pounding the ball like few others I had seen. Sinner was ranked 263rd but was finding his range and solving 59th-ranked American veteran Steve Johnson, turning around the match for a 1-6, 6-1, 7-5 victory.
The Italian crowd, who hadn’t had a men’s tennis champion of their own in decades, seemed both delighted and distinctly amused to see this improbable character score an unexpected win with an Italian flag beside his name.
Fellow Substacker Andrea Petkovic also saw Sinner for the first time that year in Rome—a few days earlier in a prequalifying event, no less, in typical Petko hipster fashion—as she wrote about earlier this year:
…A scrawny little fella, pale and freckled, red hair poking out underneath his hat. I was quite far away and while his body seemed that of a boy from where I sat, his groundstrokes were so powerful and his demeanor so adult-like that I figured it must be some 28-year-old veteran who happened to have the appearance of a youngster…Exactly a week later, I walked into the players’ lounge looking for my coach who I found in a large group of people gathered around a TV where - my coach told me - a 17-year-old was about to beat Stevie Johnson. I pushed and I shoved like I would at a good concert to catch a glimpse of the lead singer to gauge whether he’s worth fawning over for the next few weeks and I can still hear the gasp that came out of my mouth when I learned that the red-haired “veteran” was actually 17 and on the verge of becoming one of the biggest stars of the sport. The roots of his game were already there: the stoicism, the maturity, the groundstrokes.
Sinner’s ranking didn’t get him into French Open qualifying this year, but it was ticking up quickly. He had won 16 matches in a row earlier that season, I learned, a streak broken by an even younger player I hadn’t seen yet: a 15-year-old named Carlos Alcaraz Garfia.
Close-Up Magic
The second time I saw Sinner, though, was what really left an impression. Sinner, already gaining some traction in tennis nerd circles, was one of the names who popped out at me when I was looking at the order of play for the first day of Wimbledon qualifying in Roehampton.
209th-ranked Sinner was playing against 141st-ranked Alex Bolt, an Australian journeyman.
“Sinner-Bolt is a really intriguing first rounder,” Mike Cation, a commentator who clearly knows ball, tweeted when the draw came out.
Sinner and Bolt were the final match of the day on what was then called Court 2, a small court with a narrow aisle of standing room for spectators on each side. The margins of those courts in Roehampton are minimal; you really feel like you’re standing on the court right next to the players; if there are matches going on both of the courts you’re standing between, it almost feels rude to have your back turned to the other match.
Practically standing on court with Sinner, I was struck even more by his power, and the way his gangly limbs flung about gawkily but somehow effectively.
Sinner was in his first Grand Slam match of any kind—he had skipped junior Slams entirely—but he was playing like he belonged, ripping the ball and going toe-to-toe with the far more experienced grass courter. Italians were historically woeful on grass, but Sinner looked ready to break that mold.
“I’m on it—but I’m nowhere near it,” Bolt marveled as a Sinner ace flew past him on set point in the second set.
As other courts wrapped up, Sinner and Bolt continued battling. There were probably only about two dozen people there, but I was joined by a cadre of tennis writers—Reem Abulleil, Tumaini Carayol, Matt Trollope, Ricky Dimon— who clearly knew their stuff, too. We were mesmerized by the match unfolding close enough to reach out and touch. Sinner was preposterously good, but Bolt was hanging right there with him, serving lights out and using his old-school lefty serve-and-volley tactics in a way that would’ve made his Australian forebears proud.
The match was played over a now-defunct but utterly perfect format: best-of-three with no immediate tiebreak in the third set. Wimbledon was going to have a tiebreak at 12-12 in the final sets for the first time in 2019, but after hours of high-caliber battling, Alex Bolt prevailed just before what could’ve been the 12-12 tiebreak’s first implementation: 2-6, 7-5, 12-10.1
“Really got a get-out-of-jail free card there,” Bolt told reporters afterward. “I really don’t know how I won that. I really don’t know how I got through that. He played some quality tennis and I somehow just weathered the storm and I still really don’t know how I won that match.”
The Bolt-Sinner match, not taped or broadcast in any fashion as was the norm for Wimbledon qualifying in those years, gained legendary status amongst those in attendance—the ultimate underground sensation. I began referring to Bolt-Sinner as the best men’s tennis match of the 2010s: no one who was in attendance to watch it disagreed; no one skeptical of that high praise could ever prove it wasn’t the best tennis ever played. A cult following emerged: a group chat dedicated to Sinner updates and tidbits, “The Sin Bin,” was started.
The epilogue to the legend came in Lexington, Kentucky, where Sinner and Bolt met in the final of a Challenger about a month later. Because of the ceaseless ravings of those who had been in attendance at Roehampton, Bolt-Sinner II got as much hype as any Challenger final probably ever had.
The sequel—which was available to watch on a stream, unlike the original— didn’t quite live up to the legendary lore of their first meeting, but it had its moments.
Sinner won the rematch, and continued his strong play with a successful run through qualifying of the U.S. Open.
Many of the same reporters who had watched him in Roehampton gathered around a roundtable in New York to talk to him with measurably endless fascination: the interview clocked in at just over 19 minutes, probably about triple the length you might expect for an interview with a teenaged qualifier. I found the audio from that day, and hope some of you might enjoy it all as a time capsule.
One of the questions, of course, was about his instant classic against Bolt.
“I lost a very tough one against him; it was not easy in that moment, honestly,” Sinner said. “But fortunately I played against him in Lexington in the final, so it was a kind of revenge for me. I was playing better in Wimbledon, so it means that in this sport it’s very important, how you are mentally. And I think this is what I'm doing, especially this season, very good. Even if sometimes I'm a little bit nervous, but I think it's normal for a young kid.”
Sinner became a bona fide next big thing to the wider world a few months later when he won the 2019 ATP NextGen event in Milan, sending Italian fans into a lather that has never since dissipated.
As Sinner achieved more milestones—a French Open quarterfinal in 2020, a two-set lead over Novak Djokovic in a Wimbledon quarterfinal in 2022, a top- 10 ranking, a major win—those of us who had seen him first take flight on grass flashed back to that day in Roehampton again and again, not without some hipster smugness, like someone who had seen Bruce Springsteen play The Stone Pony.
When I went back to Roehampton for Wimbledon qualifying again this year, Sinner was long gone from the place, direct into the main draw as the top seed for a second year in a row.
But Alex Bolt was still there—playing his final round qualifying match on a court next-door to the court he’d beaten Sinner on six years earlier, and I was curious what he remembered about playing on a nearby court. Bolt knew immediately what I was hinting at.
“Sinner,” he said with a smile. “That was a high quality match as well. Little did we know that Jannik was gonna turn into what he's turned into. So yeah, I guess I can kind of have that little scalp on him.”
“It was just a battle from both of us,” Bolt continued. “And I mean I don't know if [the difference] was my maturity; I think he was only like 16 or 17 at the time. I’d played more on grass; maybe that was the reason I won that. But yeah, it was a massive battle.”
Did Bolt have any clue, I wondered, what Sinner was going to turn into?
“I mean, I knew he was gonna be good,” Bolt said. “I didn't know how good. But yeah, you could tell he was going to be a very special player.”
Bolt said he had practiced with Sinner in Melbourne this year, and teased him about having gotten the better of him back at Roehampton.
“We were joking about it, but then Jannik swiftly reminded me that he beat me a couple of months later in Lexington,” Bolt said. “So we shut that one down pretty quick.”
As we chatted in Roehampton, the Wimbledon main draw for this year was going to come out a day later; did Bolt relish the chance for a rematch with Sinner on grass, I wondered?
“I'll take him on a Roehampton court,” Bolt said, grinning. “But Centre Court at Wimby, I don’t know.”
As it happened, Bolt drew another tough test in the first round: eventual quarterfinalist Ben Shelton, whom he pushed to two tiebreaks in a straight-set defeat.
Sinner, avoiding Bolt striking twice at Wimbledon, went on to the final, setting up a rematch of his French Open epic with with Carlos Alcaraz.
When Sinner first found Grand Slam glory, it was on hard courts, racking up three titles in Melbourne and New York. The natural surfaces, prevailing logic seemed to suggest, would stay as Alcaraz’s domain.
But on the grass on Sunday, Sinner finished what he had started on Court 2 at Roehampton six years ago, winning his first Wimbledon title with a 4-6, 6-4, 6-4, 6-4 victory over Alcaraz, avenging his loss in Paris by holding onto his fourth set advantage this time, and becoming the first Italian singles champion in Wimbledon history.
Sinner, who will get the reigning champion’s customary honor of playing the opening match on Centre Court next year, will never need to play Wimbledon qualifying at Roehampton again. But the memory of what he showed there will live on, and it was front of mind again for me as he closed in on the trophy on Sunday.
I unexpectedly got the opening question in Sinner’s champion’s press conference on Sunday. Knowing I wouldn’t get another chance on this day, I wanted to ask him about where it all began now that he’d gone all the way.
Ben Rothenberg, Bounces: I can remember your first match at Roehampton you played here years ago against Alex Bolt. It was this crazy match, and you looked okay on the grass already. But did you think that this surface would be doable for you, from when you first experienced it and were learning about the grass, that you could someday be a champion on it?
Jannik Sinner: It finished 10-8 or something like this. 11?
Ben Rothenberg, Bounces: 12-10.
Jannik Sinner: Yeah, 12-10. No, this is a question I really don't know. I think when I was younger, you try to get as many matches as possible [on grass], trying to understand how it play on this court.
Back then if you would have asked me, I would say: ‘No chance.’ But I always felt better and better every year I played here. This year was much different than last year because I arrived here—last year I won Halle and then coming here feeling great, playing still good tennis, but lost in quarters. And this year, for sure, I felt great on court. I think we saw this also today, how I started to move better every match I played. So yeah, I'm very, very happy.
Thank you for reading Bounces, and thank you to everyone who has subscribed during Wimbledon! Bounces is back at its all-time peak of #2 on the daily Substack Sports leaderboard; if there’s ever a time to get a tennis-centric Substack to #1, a Wimbledon finals sure would seem like a good chance. So if you’ve enjoyed what you’ve read here during the tournament and would like to read even more of what was happening here behind the paywalls, I hope you can take the leap and subscribe to keep Bounces going strong and able to come back to Wimbledon next year! -Ben
Thank you, also, to everyone who joined the Bounces live chats during the Wimbledon finals, they were a lot of fun!
Programming notes: A Wimbledon notebook column will be coming later this week, and then coverage from my hometown tournament in Washington soon after that. -Ben
As it happened, the first 12-12 final set tiebreak came in the 2019 men’s final between Djokovic and Federer, a match I wrote about a few days ago here at Bounces.
Thanks Ben, I so enjoyed this particular piece. What a wonderful way to celebrate Sinner’s first Wimbledon win.
I bet your fellow tennis journalists who weren't there for the titanic Rohampton match really have retrospective FOMO.