I meet Jannik Sinner at a hotel in Monte Carlo. The day is gloomy, windy. Sinner shows up in tennis kit, a little intimidated perhaps, but with a ready wit. I tell him he seems taller than the last time we met. “Or maybe you, as you became older, got smaller,” he says.

On his wrist, he has his Rolex GMT-Master II, with a black-and-brown bezel. He takes it off so I can see the inscription on the back, celebrating his first Grand Slam victory, at the Australian Open in January 2024. That was when he beat Daniil Medvedev in the final. “That is how the most incredible year of my life began,” Sinner says.

Sinner is 23 years old. Since 10 June, he has been the world’s number one in the ATP tennis ranking: the first Italian ever to take the position. He is also the first Italian to win two Grand Slams in the same season; having won the US Open in September.

He is still young but it has been a long climb to the top. Sinner grew up in Sesto Pusteria, a village on the border between Italy and Austria. At home, his mother, Siglinde, and father, Hanspeter, speak German. When Sinner left his family at 14 to attend a tennis academy in Bordighera, near the French border—over 644 kilometres from his home—he spoke almost no Italian.

Now, he is a sensation in Italy—where tennis-school enrolments are skyrocketing, and beyond. His distinctive red hair and his rangy frame; his focus on mental health over the idea of “winning at all costs”; and his fans—the Carrot Boys—frequently sighted courtside, all make Sinner one of the most exciting personalities out of tennis. It’s easy to see why Rolex would want him as an ambassador.

“That’s a great source of pride,” Sinner says. “It’s important for me to work with [dignified] people who uphold a high standard of behaviour.”

The results speak for themselves. In addition to the Australian Open and the US Open, Sinner also triumphed in Rotterdam, Miami, Halle and Cincinnati this year, earning over EUR11m (about SGD15.6m) in prizes.

And yet, this has also been a year of huge disappointments. In May, a hip injury forced Sinner to retire from the Madrid Open. He missed the tournament in Rome. He suffered defeat by Carlos Alcaraz in the semi-finals at Roland Garros, and in the quarter-finals at Wimbledon by Daniil Medvedev. He missed the Paris Olympics due to tonsillitis.

But most of all, he had to deal with the suspicion of doping. On 10 March, at the Indian Wells tournament in California, and again on 18 March, he tested positive for less than a billionth of a gram of the banned anabolic steroid Clostebol.

He was suspended from tennis, initially for two days—4 and 5 April—before his suspension was overturned on appeal. Then he was suspended again, from 17 to 20 April. His defence was straightforward: the Clostebol, his team had discovered, had been contained in an over-the-counter spray that Sinner’s physio, Giacomo Nardi, had used to treat a cut on his own finger. When Nardi massaged Sinner, traces of the banned substance were inadvertently and unknowingly transferred to him. The ITIA (International Tennis Integrity Agency) accepted this explanation and cleared Sinner of any wrongdoing.

“It was a tough time,” Sinner tells me. “I couldn’t talk to anyone about it. I couldn’t vent or get help. All the people who knew me and watched me play understood that there was something wrong with me. I spent sleepless nights because even if you are certain of your innocence, you know that these things are complex. Everyone immediately told the truth and that allowed me to play. But at Wimbledon, on the court, I was white. And even afterwards, my feeling with people was fearful. I went into training in the Cincinnati clubhouse and thought: How are they looking at me? What do they really think of me? I realised who my real friends are.”

While it seemed that the affair was closed, in September, WADA, the World Anti-Doping Agency, announced it was appealing Sinner’s case, asking for a disqualification on the grounds of fault or negligence. This, again, throws Sinner into uncertainty, for between three and six months. Yet the spirit is firm, and the game is unaffected. In October, he reached the final of the China Open in Beijing; in November, Sinner clinched victory over Taylor Fritz in the ATP Finals in Turin.

“I have grown so much this year,” he says, “Both mentally and physically.”

ESQUIRE: How do you explain your ascent to the top?

JANNICK SINNER: The results you see now are not sudden. They are the fruits of the hard work we have done over the past two years. I am the son of a chef, and I know that you don’t start cooking a good dish in a few minutes. You study, understand, try and try again—then the final dish will be good.

ESQ: What was the biggest thing you learnt on the court?

JS: Tactics. It is important because it can allow you to adjust a game that is not going well. When [former Italian tennis pro] Simone Vagnozzi came to my team, he gave me seven to eight pieces of information per game. I honestly didn’t understand anything. He told me: “Every now and then, you [need to] make a slice.” But I didn’t know how to do it, so we made a lot of changes. It’s a shot [that] I don’t even do technically correct because I hold the racket with two hands.

Still, I [now] feel more confident with it. Simone is good because we [have a lot of discussions] and he doesn’t impose rules on me. He asks me to be more fluid [in my serves like] touching the ball in the right way, which also means spending less energy.

ESQ: How do you think you can improve?

JS: In the US Open final, I didn’t serve well. That can happen. But that is a shot for which there is great room for growth. I’m convinced that, no matter how much you practise, you always have to deal with a bad day. But it’s important to be able to vary your shots, to feel more confident when going down to the net, to work on your bunt, to have a different feel for the ball.

ESQ: Can you describe your style to someone who knows nothing about tennis?

JS: It’s a mix between solid and aggressive. I struggle more defensively. In fact, I try not to go into defence. My tennis is versatile, but, for example, I still don’t know how to play the net game well. A player who has made me grow a lot is [Daniil] Medvedev. I had never serve-and-volley [but] he forced me to practise that to [to gain an advantage in beating] him. Against some players, I have to do more of a long backhand. In tennis, you learn from your relationship with your opponent. The real question for the tennis player is: how do I get into the opponent’s head? If you guess the answer, things in the match change.

ESQ: Amid all this chaos, how do you maintain your composure?

JS: Accepting myself. I have matured; I understand myself more. It may sound silly but getting to know yourself is fundamental. I worked on it a lot with [sports psychologist] Riccardo Ceccarelli. During the game, it’s easier for me—I forget the mistake easily. During training, on the other hand, I quickly look for improvement. That is wrong. When I started to admit [my flaws], I made small steps moving forward.

ESQ: Does having a winning mentality change you as a person?

JS: No. We always talk about results. For me, they are the consequence of what you express on the court. When you are at a high level and the body holds up, you don’t have to question yourself because the results will certainly come. My family understands me and my team understands me, maybe even better than my parents. I find my peace of mind with them. We live in hotels, planes; we travel all the time. They allow me to be the [man that] I am and understand what I need.

ESQ: For example?

JS: Simple things, such as indulging some of my passions. I love driving. It makes me feel great. Alone, isolated; I put the music on and every now and then, I’d [turn off the music to] hear the engine and I get charged up.

ESQ: Your girlfriend is fellow tennis player, Anna Kalinskaya; what has she added to your life?

JS: I don’t think anything has changed. Having a girlfriend is something that either makes you feel good or makes you feel bad. I want it to be something that feels very natural, [something that] comes into my life normally. I can’t afford to change as a player or as a person. That hasn’t happened so that’s why it works.

ESQ: Does nothing affect you?

JS: It’s not easy to play when there’s a personal tragedy. Knowing that my aunt Margith, who did so much for me as a child, was dying, certainly affected me.

ESQ: Do you ever reflect on the fact that you are the most successful Italian tennis player ever?

JS: You won’t believe it but it has never been a goal of mine to be the most successful in anything. For me, I place more value on what kind of person I am; what kind of people I surround myself with; what degree of trust I can have in them. I don’t believe that if you win, then you are good, and if you lose, then you are not good at all. Each of us has our own talents. The luck lies in finding a way to express them.

ESQ: Yes but being the champion changes things, doesn’t it?

JS: You face a lot more pressure. But I really believe that there is no money that can replace being healthy and living your life surrounded by people you love.

ESQ: The great football player Alessandro Del Piero once told me: “Losing makes me sick.”

JS: I am more of the belief that you are either winning or learning. For me, losing often to Novak Djokovic taught me a lot. It’s good for you; it wakes you up. In football, you might play against Ronaldo and realise you need to prepare better next time. But when is the next time? In tennis, we have more opportunities to make up for it.

ESQ: What did you get wrong this year?

JS: Tennis is important, but I didn’t spend enough time with the people I love. I have to find time for that because some things pass and never come back.

Photography: Philip Gay
Styling: Nik Piras
Grooming: Gianluca Grechi using DEPOT – THE MALE TOOLS & CO.
Lighting Assistants: Carlo Carbonetti and Leonardo Galeotti
Styling Assistant: Marco Visconti
Production: Sabrina Bearzotti