NEW YORK — As he rode past Grand Central Station the other day, Roger Federer’s mind drifted back to 1998, and his first trip to the U.S. Open.

He was playing in the boys’ event. He stayed at the Grand Hyatt, right next to Grand Central. He shared a room with his doubles partner, Olivier Rochus of Belgium.

They had won the Wimbledon boys’ title together earlier in the summer; they figured they would try to double up, but instead lost in the first round. Federer had better luck in the singles, making it to the final, where he lost to David Nalbandian.

When they weren’t at the Billie Jean King National Tennis Center, he and his coaches wandered around Midtown. Federer’s eyes were wide open, just as they had been when he was 14 and traveling to the U.S. for first time.

“It gave me a similar vibe, that I need to come back,” Federer said during another New York car ride in late August, from Flushing Meadows back to Manhattan. “I fell in love with New York and the energy. Then I came back the following year, lost in the qualies (qualifying), second round against a good friend of mine, Swiss guy. And then after that, the main draws came.

“It was a great run.”

It was. Twenty Grand Slam titles, five in a row at the U.S. Open and six in all. Still the last man to defend the title here. And that’s just in New York.

This week, Federer’s mind is doing something it doesn’t often do. He’s letting it roll back through the years. On Monday, he walked onto Arthur Ashe Stadium for the first time since 2019, the last time he played in the tournament. On Saturday, he will be inducted into the International Tennis Hall of Fame in Newport, R.I., the first of a long line of generational talents from the 1990s and 2000s to receive the honor. Rafael Nadal, Serena and Venus Williams and Novak Djokovic will have a week like this in the coming years.

Five years after his last singles match, at Wimbledon in 2021, Federer is ready to remember.

It is proving therapeutic, even if it has all come on a bit too fast. The 45-year-old didn’t retire from tennis until 2022, at the Laver Cup in London that has gone down in tennis’ emotional folklore, all tears shed and hands held. But because his last official match was a year earlier, he met the five-years-removed criteria that the Hall of Fame imposes.

It’s an opportunity for perspective, something Federer said he needed. He’s adjusted. He’s found a way to rediscover some poetry in what he did on and off the court during his career, the poetry which came so naturally in the moment but has since been dormant.

“It’s nice for me to open the door quickly and peek inside of my past, of my tennis career, because I do very little of that nowadays,” he said, as the SUV rolled past LaGuardia Airport.

“I don’t do many interviews, I don’t think about it often. I don’t get asked that much, because I move in circles where I don’t get asked a million times about every single detail.”

This week though, is different, and he’s good with it. He is thinking about it. The memories are flowing in ways they never have, because it’s impossible to watch a movie and star in it at the same time. Even when Federer retired, the emotion of it all, the magnitude of a career that belonged to one of the most beloved players ever to swing a racket, got in the way of reflection.

“When you retire, you never truly close the book. Maybe you do it on the entirety of your career, but then … maybe New York was a part of that. Maybe your hometown tournament was a part of that. You had so many emotional spots or people that trigger you that you can never fully close it,” Federer said.

This, he thinks, will be different. The Hall of Fame is the ultimate valedictory. It enshrines a player’s individual contribution to the sport while reminding them that they are but a star in a galaxy. It even got Pete Sampras warm with nostalgia. Just wait, Federer said Sampras warned him years ago. It’s all going to hit you.

“I’m still young enough to let it come back to me. You know, I’m an emotional person, so I think the Hall of Fame allows me to really have a nice look back at everything I achieved, what I will represent. I guess the biggest thing is a giant thank you to everybody who has helped me reach today.”

Roger Federer played an exhibition at the Tennis Hall of Fame in Newport, R.I. ahead of his induction. (Joseph Prezioso / AFP via Getty Images)

New York was a good place to get the party started. He may have won his last title there nearly 20 years ago, in 2008, longer ago than his last Australian Open, French Open, or Wimbledon triumph. But his record of five consecutive U.S. Opens has a certain gravity.

Listening to him talk about New York, it’s obvious how Federer managed to stay in orbit.

He learned to feed off the energy of the city. He embraced its glitz and glamour. One year he stayed in Greenwich, Conn. Never again. Once on site, he found a little room where he could find his zone of quiet and focus on his business.

It got harder toward the end. His fame had made him as big a celebrity as the ones who gazed at him from their courtside seats. As he spent the better part of two days around the National Tennis Center, the week before the U.S. Open main draws get under way, he was still barely able to take a few steps without someone asking for a selfie or an autograph.

That even happened in the player areas. The people grinding their way through qualifying or practicing are mostly in their late teens and early 20s. They grew up worshipping Federer like any other tennis fan, but many of them, if not most of them, have never been at the same tournament site as him.

Still, that doesn’t happen in other sports. The new guy the New York Yankees just called up from the minor leagues isn’t asking for a selfie with a Hall of Famer like Derek Jeter when he walks into the clubhouse. That guy will try to play it cool, to show that he’s sort of in the same club. Figureheads are there to be emulated.

Not Federer. No one will ever be like him, the essence of drive and effort disguised by effortlessness on and off the tennis court. He handles it all in the usual way.

“People wanting to meet me, see me, take pictures and not only here, but then the city, and traffic and it’s just a lot. But I always embraced it.”

He embraced it so much that he came back just about as quickly as he could, following his retirement. Not for tennis. To host the Met Gala in 2023.

Roger Federer won five consecutive U.S. Open titles between 2004 and 2008. He remains the last man to defend a title in New York. (Don Emmert / AFP via Getty Images)

Federer was always different, in one way more remarkable than all the rest. The thing so many of the greatest of the greats crave in retirement is the thing they can’t replicate. That adrenaline rush that can only come from walking into the cauldron of high-stakes competition with tens of thousands of fans in the stands and millions watching at home, and then putting everything on the line. No business meeting or appearance will ever replace it.

Federer? He is OK with that. When he explains why, he gives something like a wince.

“I’m actually relieved I don’t have that any more. The pressure cooker and all that stuff is a lot to take,” he said. “It’s a relief not to go through those … Let’s say, knots in the tummy, time and time again. It made me … I don’t want to say tired, but — ”

He exhales. He is remembering.

Instead, he loves to watch other famous people and elite performers practice their craft. Concerts. Rugby union’s World Cup. Tennis at Wimbledon and the Laver Cup, the team competition he and longtime business partner Tony Godsick created. It’s fun to be the fan, wondering what a favorite singer or great athlete in another sport can do, or what they are thinking in the moment.

Saturday, he will get his turn. This is his first time in Newport, one of America’s storied playgrounds. Somehow, he had never made it to the Hall of Fame.

He is not exactly sure how that happened. He was one of those players who loves to geek out on tennis history. He named his team competition for Rod Laver to honor one of his heroes of the past. He’s into this stuff.

He scheduled time to look around and soak in the story of the sport and see how he fits into it. He had an idea, but it’s not something he dwells on regularly.

Then there is the small matter of his speech. He delivered the commencement address at Dartmouth’s graduation in 2024. He crushed it. It has become one of the most-quoted speeches of the genre, which usually involves famous people talking about their success and patting themselves on the back. Federer, who has had more success in his chosen endeavor than just about anyone else has had at theirs, spoke about failure.

He talked about losing nearly half the points he played. He spoke about his loss to Rafael Nadal in the 2008 Wimbledon final. He spoke about the most important thing for any tennis player, and maybe for any person — focusing on what happens next.

The Hall of Fame speech will be different.

“I’m not teaching class,” he said. “This is more of my personal perspective. It’s nice to go to these emotions.”

He’s doing what he did when he played. Visualizing. Imagining what it’s going to be like to drive to Newport, to receive the warmth and the gratitude, and to give it back. That’s important to him. It always has been.

Will he turn into a puddle once more?

Federer grew up at a time and in a place where men showing emotions, especially athletes, was not much of a thing. He can’t remember seeing a Swiss soccer or hockey player or skier, or really any sporting hero of his, cry. Maybe Michael Schumacher cried once, he thinks.

Tiger Woods cried a bit. So did Michael Jordan. He never figured he’d be like them. Then he and his Swiss teammates beat an American team that Patrick McEnroe led to the Davis Cup in his hometown of Basel. The Swiss had never beaten the Americans before. Lots of tears for that one. McEnroe is now the president of the International Tennis Hall of Fame; he will help manage the weekend’s ceremonies.

Roger Federer stepped on to Arthur Ashe Stadium for an event in his honor ahead of this year’s U.S. Open. (Garrett Ellwood / Getty Images)

A few months later, Federer beat Sampras at Wimbledon. A puddle once again. He couldn’t believe it.

“The more I tried to hold it in, the more sometimes it came out,” he said. That informs his expectations for Saturday.

“I’m not sure yet what it’s going to be like. I wish I knew, but at the same time, it’s good to be surprised. I might get through the whole speech completely at peace, or I’ll go through so many moments that I’m going to get hit by emotions.”

Earlier in the ride, somewhere just outside the Tennis Center, Federer was again trying to remember. He knew that in between retirement and this week, in those four years of letting everything he had achieved marinate, he had actually been to the U.S. Open. He couldn’t quite place it, the year and the reason. But something did stick in his head. He was in a suite in Arthur Ashe Stadium, hobnobbing the way legends of the game do. Watching the stars of today with some other players from his era.

At some point in the match, the tournament flashed Federer’s image on the big screen, his face and his suit jacket and his boldface name in lights. The 24,000-or-so fans inside cheered and whooped. Roger Federer, and all that he represented, in the same room as them.

“That wasn’t a farewell moment for me,” Federer said. “I haven’t really been here.”

He is here now. It was time.

We have an action-packed day’s racing on Saturday with flat action from Chepstow, Windsor and Saratoga, live on Sky Sports Racing…

6.30 Windsor – Ghostwriter, Tenability and Silawi headline

The feature event on a splendid card at Windsor sees Ghostwriter and Tenability headline nine runners for this Listed August Stakes.

Ghostwriter has attracted a lot of attention since Amo bought him for £2 million back in June 2025 and he has yet to reward his connections. A classy operator at his peak, he showed he might be building towards a big performance when fourth at Goodwood and this looks a good fit.

Silawi, winner of the Grade One Canadian International at Woodbine last year, ran a cracker when runner-up in the Jebel Hatta in January but has not hit those highs since. Well beaten in Germany last month, he will hope to bounce back at a track that suits.

Tenability shoulders a three-pound penalty for his Tapster Stakes success at Goodwood but usually runs his race, while Warrant Holder is another for each-way players to ponder.

4.30 Windsor – Debut winner Crown And Two bids to go 2-2

Debut winner Crown And Two bids to remain unbeaten in the opening Matchbook Betting Exchange Supporting UK Racing Novice Stakes at Windsor.

The Tom Clover-trained colt created a fine impression when landing a Newmarket novice 23 days ago and he rates the one to beat if handling these slower conditions.

George Boughey’s Arthur Carrot broke slowly when second to Mithaaly at this track earlier this month and he should be sharper on this occasion.

Others to note include William Haggas’ twice-race Bulletsnap while Blue Victory remains capable of better after his debut fifth.

4.40 Chepstow – Recent winners Minster Man and Roxa Love clash

Last-time winners Minster Man and Roxa Love clash in a cracking Sky Sports Racing Sky 415 Novice Stakes at Chepstow.

Minster Man chased home the useful Evenfall on debut before landing a Musselburgh novice with plenty to spare. A fine big type, he will be expected to improve again and could defy an opening mark of 85.

Roxa Love built on her debut when outpointing Henley On Thames at Brighton and with that rival winning at York last week, she must be of interest under Pat Cosgrave.

Eve Johnson Houghton’s Crazee In Havana rates best of the rest.

Best of the rest

5.00 Windsor – The in-form Under The Twilight features among nine runners for fair Class Four contest.

5.45 Chepstow – A fascinating contest with the beautifully-bred colts Flight Tracker, Mainshock and Saxon Lodge involved.

7.10 Caulfield – Group One Memsie Stakes – Jimmysstar and Cosmic Crusader headline.

10.40 Kentucky Downs – Grade One Kentucky Downs Ladies Turf Sprint Stakes – Sayidah Dariyan represents Richard Hughes. Ag Bullet bids to win this again.

8.19 Saratoga – Grade One H. Allen Jerkens Memorial Stakes – Englishman a warm order for Cherie DeVaux.

8.55 Saratoga – Grade One Personal Ensign Stakes – Fully Subscribed and Scottish Lassie feature.

9.33 Saratoga – Grade Two Lake Placid Stakes – Charlie Clover saddles Flowerhead.

10.11 Saratoga – Grade One Forego Stakes – Book’em Danno will be a short-price fav.

10.49 Saratoga – Grade One Resorts World Casino Ballerina Stakes – Ways And Means headlines.

11.35 Saratoga – Grade One DraftKings Travers Stakes Golden Tempo, Renegade and Sea Strike contest a red-hot heat.