It was moving day in the California desert, and Roger Federer was up before dawn. We met on the tarmac in Thermal, a short drive from Indian Wells, where Federer had lost the day before in the final of the 2018 BNP Paribas Open to Juan Martín del Potro. Just the previous month, Federer had capped his remarkable late-career surge by reclaiming the No. 1 ranking for the first time in more than five years. At 36, he was the oldest player to hold the spot since the A.T.P. published its first rankings in 1973. But Indian Wells was a rather disappointing sequel. He served for the title against del Potro at 5-4 in the third set and failed to finish him off despite holding three match points.
It was the sort of reversal of fortune that happened rarely — but more often to Federer than to his rivals at the top of the game. He has lost more than 20 times after holding match point, while Rafael Nadal and Novak Djokovic have lost fewer than 10 such matches. “I know it’s bad to say this,” said Günter Bresnik, one of tennis’s top coaches, who has known and respected Federer since his teenage years, “but I sometimes call Federer an underachiever in tennis, considering all the matches in big tournaments he lost being already up. The guy should be at 30 Grand Slam tournaments if you’re talking about del Potro, Djokovic, Nadal and all these matches he lost where he was clearly ahead.”
And yet as we talked on the tarmac, Federer, with his long-horizon perspective and preternatural ability to compartmentalize, seemed well equipped to cope with the letdown. He was far from grumpy as he chatted and yawned in the cool of the early morning on too little sleep. “Five hours,” he said. “Not enough after a match like that.”
He was soon cleared to board the private jet that would take him to Chicago. I was along for the four-hour ride: a chance to get an extended look at a day in his business life as he toured the next venue for the nascent Laver Cup, a pet project of Federer and his longtime agent, Tony Godsick. Federer did not collaborate with me on the book from which this article is adapted, but I have followed him on six continents (the Antarctic tennis scene has yet to take off) and interviewed him more than 20 times over two decades for The New York Times and The International Herald Tribune. Our meetings have taken place everywhere from a back court at Wimbledon to the back seat of a chauffeured car in Buenos Aires; from Times Square to the shores of Lake Zurich. In Paris, I once enjoyed a ridiculously good view of the Place de la Concorde from Federer’s suite at the Hôtel de Crillon while his future wife, Mirka Vavrinec, tried on designer clothes. But traveling with him and his team on a plane was the highest level of access I’d been granted to date, and a sign of how eager Federer and Godsick were for their brainchild to succeed.
The Laver Cup, named in honor of the Australian great Rod Laver and inspired by golf’s Ryder Cup, seemed straightforward enough as a concept: three quick-hitting days of tennis each year that matched the best of Europe against the best from everywhere else, with Federer getting the unprecedented chance to play on the same team with Nadal or Djokovic. Despite the complications that inevitably accompanied attempts to do something new in tennis — reaching consensus among all the competing interests, finding room on the sport’s crowded schedule, getting the biggest stars to take part — the first Laver Cup in 2017 turned out to be a smash hit. Held in Prague, it attracted sellout crowds to watch Federer and Nadal join forces, victoriously, as doubles partners. But in the end, it lost significant money, because of the start‑up costs and generous participation payments.
It was important to Federer that the second year’s event would build on the positive first impression. This was why he was heading to Chicago while Mirka and their four children — who, to a degree that was unusual for professional tennis, traveled full time as a family on the tour with Federer — went to Florida separately to set up base camp for the Miami Open, which would start that week. “Laver Cup is something that is very dear to me, so clearly I always have extra energy for the Laver Cup,” Federer told me. “For my own career, I don’t play as much anymore, and when I am there, it’s all out and full speed, and then I need the time away again.”
Federer did not own a plane but was traveling on one provided by a company that sells fractional private-jet ownership. Federer used the service when he traveled within North America and often within Europe. It was all part of the plan to reduce the friction in his complicated global life: to make the transitions, the jet lag and the rest of his off-court existence as smooth as possible for him and his family. “I don’t need all this,” Federer said, gesturing at the plane. “It’s just an investment in yourself in terms of energy and management. Not having to beat so many checkpoints and lines and people and pictures, so I can get into the plane, and I can relax already now.”