Jannick Sinner Esquire
Photography: Philip Gay. Styling: Nik Piras
Jannick Sinner Esquire
Photography: Philip Gay. Styling: Nik Piras



GROWING UP, WE had a tennis club down the street. It started out as your typical neighbourhood club, with a few courts in need of repair and a clubhouse roof that would leak when it rained. Then, over the years, with an ambitious manager at the helm, it transformed into one of the biggest clubs in the country, complete with its own gym, spa and performance centre known for creating a Grand Slam champion or two. (Note to reader, I am not one of those said champions – that isn’t, alas, where this story is heading.)

Through its various rebuilds and refurbishments, the club’s lifeblood remained a small but devoted group of locals, who, like true Brits, would brave the weather all year round to get out on the court for a game. For a time, in my early teens, I was one of them. Every weekend, if I wasn’t at home, I was either on the court playing doubles with my friends or I was in the clubhouse digging spare change out of my bag to buy a can of Sprite and a packet of Fruit Pastilles. When things got more serious, I was spending my weekends on the road with my mum, entering tournaments up and down the country in the hope of winning precious ranking points. I was playing every day and loving every minute of it.

Then, somewhere along the way, I fell out of love. It was all getting a bit competitive and, besides, very few of my high school friends were playing tennis – they were all playing hockey – so I decided I wanted to be part of a team. The lessons stopped, the racquets didn’t get restrung, and we soon moved house. I was a tennis has-been by the age of 15.


Clockwise from top left: Christopher Riley, tasting success as a junior tennis prospect, in the colours of his local club; in the orbit of Lleyton Hewitt, at Queen’s Club, London; unleashing his forehand on the hardcourts of his youth.


As I was hanging up the racquet, a man by the name of Roger Federer was starting to make himself known. It seemed like all the energy I had channelled into playing got redirected into becoming a Federer fanboy. I had admired Sampras before him, and being a Brit, I will always have a soft spot for Tim Henman and Andy Murray, but for me, the Swiss master wasn’t just the best, he wasn’t just the coolest, it was as if he alone embodied the essence of how the sport was supposed to be played. Nadal and Djokovic might be more efficient – perhaps even more effective – but Federer was cut from a different cloth, an artist among athletes.

The next 20 or so years, with power shared among the Big Three, was the greatest era the sport has known. Now, tennis is in a very different place. On Federer’s retirement, the single- handed backhand moved a step closer to becoming a relic of a bygone era – its comparative lack of racquet control deemed unsuitable for the modern game. At the same time, tournaments became more open and competitive, as the next generation of stars vied to fill the vacuum left by Federer’s departure and Nadal’s slow decline.

First, it was Carlos Alcaraz who stepped up. A US Open winner at 19, the Spaniard plays with an almost childlike freedom that makes him both a joy to watch and a confounding opponent. But while Alcaraz’s potential is vast, he is not yet the finished product.

Treading a more measured path to greatness is Jannik Sinner. The Italian, a former skier, plays with a ruthless efficiency that contrasts with Alcaraz’s freewheeling creativity. I was in the stands when Sinner won his maiden Grand Slam title at the 2023 Australian Open. When he lost the opening two sets to Daniil Medvedev, it’s probably fair to say that everyone in Rod Laver Arena thought the contest was over. Except Sinner. It may have been his first major final, but the then-21-year-old was unfazed by the occasion. Slowly and methodically, he picked apart Medvedev’s game until there was nothing left of it. The Italian followed up his AO win with victory at Flushing Meadows, as well as at the recent ATP Finals in Turin, ending the year as the undisputed world No.1.

Jannick Sinner Esquire
Photography: Philip Gay. Styling: Nik Piras

Sinner and Alcaraz are not the Big Three. Nor are they trying to be. Each has a style all his own, and, more than that, the sport to which they belong is now a different beast.

While Federer was a master of style, on and off the court, I don’t recall the Swiss star ever walking onto Wimbledon’s centre court carrying a Gucci duffle bag, as Sinner did last year. Nor can I recall a zeitgeist-defining film about tennis during the era of the Big Three, as we saw with this year’s Challengers. This new generation is not just athletes who occupy the newspaper back pages four times a year when the Grand Slams come along. They’re cultural tastemakers, operating at the intersection of fashion, sport and popular culture. And, in the case of Sinner, they’re magazine cover stars.

Read our cover story starring Jannnik Sinner here.

The ‘Summer of Tennis’ issue of Esquire is on sale December 9. Find your nearest stockist.