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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.”‘The thing I’m most jealous of is not the skill and not the titles,’ Andy Roddick said. ‘It’s the ease of operation with which Roger exists.’Federer had the means at this stage in his career to reduce a great deal of friction. He was on his way to becoming one of the few athletes in history to earn $1 billion during his playing career, a milestone he reportedly surpassed this year, joining Tiger Woods, Floyd Mayweather, LeBron James, Cristiano Ronaldo and Lionel Messi. Federer’s two decades of on-court achievements only begin to account for that stunning total: About $130 million of Federer’s earnings has come from official prize money, a figure that puts him second on the all-time list in tennis to Djokovic’s $152 million. The rest has come through sponsorships, endorsements, appearance fees at tournaments and lucrative exhibition events around the world. Federer’s performance in this domain has been every bit as impressive as his performance on court — perhaps even more so when you consider the disadvantage he started with. Sponsorships and endorsements tend to be easier to acquire if a tennis player comes from a major market like the United States, Britain or France. But because Federer hails from Switzerland — a wealthy place, to be sure, but also one with a population of only about 8.6 million — his appeal to potential sponsors at the beginning of his career was hampered. “When you are Swiss, you represent a small country,” said Régis Brunet, Federer’s first agent. “If you want to make serious money, being No.10 in the world does not suffice.”In the run-up to this year’s U.S. Open, with the announcement that a third operation on his right knee will sideline Federer for months, perhaps even permanently, it is not too early to begin to assess the career of this remarkable figure. Some might still claim that he is the greatest player of all time, but considering Djokovic’s and Nadal’s achievements, it’s debatable whether he’s even the greatest player of this era. What is undeniable, though, is that no tennis superstar has ever built a financial empire comparable to Federer’s — and that this, more than his greatness as a player, might well be his most enduring legacy. If the bedrock of that billion-dollar brand has been his phenomenal on-court talent and graceful game, what he has built off the court has also been based on some extremely rare qualities: impeccable strategic instincts, along with the sort of personality that might be more suited to a boardroom or a political campaign than to a pro-sports arena, all combining to make Roger Federer the greatest player-mogul the tennis world may ever see.In late 2002, it was obvious to most perceptive tennis watchers that Federer, then 21, was on his way to becoming a major player. He was ranked 13th and about to break into the top 10; most notable, he had upset the great Pete Sampras in the fourth round of Wimbledon the previous year. His own first Grand Slam title, at Wimbledon, was less than a year away.But at that point, there was not even a whiff of the billion-dollar empire builder that Federer would soon become. That year, his agent, Bill Ryan, surprised him at the U.S. Open by informing him that he was leaving the sports-management giant IMG, in circumstances so contentious that Ryan could not even explain them. “When Bill left IMG, we weren’t allowed to work with him,” Federer said to me later. “I don’t know what the reason was.”The timing was particularly bad because Federer’s five-year sponsorship contract with Nike, with an average value of $100,000 a year, was expiring, with negotiations still ongoing; Ryan had refused to accept a renewal offer from the company that he felt was too low and had been unable to find a competing sponsor to step in. “They were only offering him $600,000 a year,” Ryan told me about Nike. “Roger’s father was begging me to take the deal, and I said: ‘Robbie, your son is going to be the best player who ever walked the face of the earth. Why would I accept a $600,000 deal?’”Ryan believed, based on Federer’s on-court potential and other players’ contracts, that the young star should be getting at least $1 million guaranteed from Nike in the first year of the next contract. “Roger was on board,” Ryan told me. “But I still have the email from Robbie saying: ‘Bill, you have to talk Roger into taking this deal. He needs the money.’”With Ryan gone, Federer consulted with Mirka and his parents and made a remarkable decision: He would break ties with IMG and set up his own management team with his family. “We thought about looking for another manager, and I finally said, ‘I think we should try to handle things on our own for a while,’” he told me in Paris in 2005.This decision was far from an unalloyed success, especially at first. And it presented a cause for concern for many within the tennis industry, including rival agents like Ken Meyerson, a hard-charging American who represented Andy Roddick until 2011, when Meyerson died from a heart attack. “I feel Roger is terribly, inadequately represented and feel there are millions and millions being lost,” Meyerson told me in May 2005, when Federer had already been No.1 for more than a year and won four Grand Slam singles titles.Roddick had won one major title at that stage and was ranked No.3, but Meyerson had just closed a lucrative long-term deal for him with the French apparel manufacturer Lacoste. It reportedly paid Roddick about $5 million annually and compared very favorably with the multiyear Nike renewal that Federer finally signed in early 2003. “I can honestly say we’ve got a substantially bigger deal than Federer, and yet Andy is clearly lower-ranked,” Meyerson said. “Whoever negotiated his current Nike deal certainly did a disservice to those who are out there representing commensurate talent. It brings down the entire market if the father, because of his inexperience, thinks a deal is worth X, and it is really worth 10 times that.” Meyerson estimated that Federer’s Nike deal paid him at best between $1.75 million and $2 million annually. “It should be worth $10 million per year,” Meyerson told me.It was also instructive to compare Federer’s fortunes with those of the women’s star Maria Sharapova, who won Wimbledon in 2004 at age 17. Her off-court sponsorship deals were approaching $20 million a year by the end of 2005, according to IMG executives, who said that Federer’s did not even total $10 million. “We were crushing deals, and we were miles ahead of where he was,” said Max Eisenbud, Sharapova’s longtime agent at IMG.In 2005, the year after Federer won three of the four major tournaments, Forbes estimated his annual earnings at $14 million — a figure that placed him well behind Andre Agassi ($28 million) and Sharapova ($19 million). Federer explained to me at the time that he enjoyed his independence and did not want to overcommit to sponsors because of the demands that would generate on him. But he clearly took note of the disparities, and of the demands on Mirka, who was busy managing his media relations and agenda.Illustration by Ryan MelgarFederer’s business career took an important turn in August 2005. That month, while in North America for the tournaments leading up to the U.S. Open, he decided to meet with management agencies. IMG had a new chairman and chief executive: Ted Forstmann, a billionaire and tennis aficionado whose private-equity firm acquired IMG in 2004. Forstmann was aware that other IMG executives had tried without success to bring Federer back into the fold. He knew the former No.1 Monica Seles and asked if she would help arrange a meeting. Seles agreed, reached out to Mirka and took part in the meeting. It went well: Forstmann and Federer connected by talking about South Africa, where Federer’s parents fell in love and where his recently started foundation was working to help children living in poverty. Forstmann had taken in two South African boys from an orphanage he had funded after touring the country with Nelson Mandela.Seles also vouched for her own IMG agent, Tony Godsick, and Roger and Mirka agreed to sign on. It was a decision that quickly led to a major change in Federer’s bottom line. By mid-2010, his annual earnings had ballooned to an estimated $43 million, according to Forbes. That included deals with the German automaker Mercedes-Benz and internationally focused Swiss brands like Rolex and Lindt chocolates.In 2008, Federer renewed his Nike deal for 10 years, reportedly at more than $10 million per year, which was believed to be a record for a tennis endorsement. This time, there were no complaints that he was bringing down the market. Godsick was also trying to bring Federer into the mainstream in the United States, perhaps the toughest market for a European tennis player, in part because tennis is a niche sport in North America compared with the major team sports. “In the beginning of the career, everybody talks about America,” Federer told me. “ ‘Have you done it in America? Are you famous in America?’”Some sponsorship contracts stipulated that Federer get exposure in the United States. So it might not be a coincidence that around this time, Federer forged an acquaintance with Tiger Woods. Each was represented by IMG and sponsored by Nike, and in 2006, Godsick and Woods’s agent, Mark Steinberg, who were friends, arranged for Woods and Federer to meet at the U.S. Open tennis tournament in New York. Their mutual admiration seemed genuine. Woods declared himself a “huge Federer fan” during the British Open in July 2006, which he won, and when I interviewed Federer several weeks later in New York, he spoke at length about being inspired by Woods’s example. “I do draw strength from it,” he said.Federer and Godsick were also interested in maximizing his commercial potential. Gillette, the Boston-based razor company, was looking for brand ambassadors to succeed the soccer star David Beckham. It was already focused on Woods and had winnowed the other final candidates to a small group that included Federer and Nadal. A real-life connection with Woods surely could not hurt. When Federer faced Roddick in the 2006 U.S. Open final, Woods met Federer beforehand. When the final began, Woods was in the front row of Federer’s box with his wife, Elin Nordegren, on one side and Mirka on the other. “It wasn’t some stunt to get the Gillette deal,” Godsick said. “Tiger and Roger just wanted to meet. The U.S. Open was the only time we could make it work.” But the optics, with Woods at the peak of his fame, were clearly valuable to Federer. In February 2007, Gillette named Federer a brand ambassador, along with Woods and the French soccer player Thierry Henry.The relationship with Gillette lasted longer for Federer than it did for Woods, who in 2009 had to deal with revelations of his serial infidelity and the subsequent collapse of his six-year marriage. Agents within the sports industry believe that Federer benefited from the implosion of Woods’s image. “It took Roger a while, many Grand Slam victories, to get it going,” Max Eisenbud said. “But I’ve just never seen a more complete package than him, and I think when a lot of things started to happen, the Tiger Woods controversy, and brands started to get really uptight and worried about brand associations, Roger really catapulted himself because he was as safe as safe could be.”By 2013, Federer’s annual income had reached an estimated $71.5 million, boosted by his first South American exhibition tour and a new endorsement deal with Moët & Chandon. That put him second on the 2013 Forbes list of the world’s highest-paid athletes, behind Woods and ahead of the basketball star Kobe Bryant. Still, the bulk of his staggering financial success was in his future. And the factor that allowed that incredible liftoff to take place was, above all, his singular personality.The French have a fine expression that applies to Federer: “joindre l’utile à l’agréable,” which translates loosely as “combining business with pleasure” but is actually broader in scope, encompassing the tasks of daily life. If you wonder how Federer managed to remain in the top 10 until age 40, part of the answer lies in his ability to embrace what some other prominent athletes might consider drudgery. That applies to long-haul travel, news conferences in three languages and mundane one-on-one interactions with various corporate partners.It is in that last category of task — his knack for delivering personalized service with sponsors — that Federer’s performance has been especially remarkable. Even in his early years, he would endeavor to visit all 20 of the sponsor suites at the Swiss Indoors to meet and greet. He has stuck with that philosophy. “He’s just so good if you’ve seen him with sponsors, with C.E.O.s,” Eisenbud said. “He just has the ability to make you feel like he really cares what you are saying and he has time for you. He’s never rushing you. If you’re a fan at a hundred-person event that one of his sponsors puts on and you are talking to him, he makes you feel he has all the time in the world to talk to you and hear what you have to say. I think it’s genuine, and I’ve never seen another athlete like that, and I think it has a lot to do with how he was brought up.”Mike Nakajima, who was a director of tennis at Nike, remembered Federer coming one year to the company’s headquarters in Beaverton, Ore., for shoe testing at Nike’s research lab. They walked out of the building and were headed for their next meeting when Federer stopped in his tracks and said, “I’ve got to go back.” Nakajima asked him if he had forgotten something, and Federer said he had forgotten to thank the people who helped him with the shoes. “So we ran back into the building, downstairs, through security so he could say thanks,” Nakajima said. “Now what athlete does that?”The French have a fine expression that applies to Federer: ‘joindre l’utile à l’agréable,’ which translates loosely as ‘combining business with pleasure.’Federer was at Nike headquarters for “Roger Federer Day,” in which all the buildings on the sprawling campus were temporarily renamed for him. But Nakajima said the day was not simply a celebration of Federer’s achievements. Federer, often up for a prank, agreed to play a few on Nike’s employees. They brought the advertising team together to watch a new advertisement. Federer surprised them by wheeling a cart around the room and serving coffee and doughnuts. At the company gym, he sat behind the front desk and handed out towels to the employees. At the company cafeteria, Federer did a shift as a cashier and then as a barista. “Of course, he didn’t know how to make coffee, so what he ended up doing was he just went around, going table to table, saying, ‘Hello, my name is Roger Federer, nice to meet you,’ as if people didn’t know who he was,” Nakajima said. “You think you could get Maria Sharapova to do that? No way. And Roger did that with a smile on his face, and then he played Wii tennis with anybody who wanted to play with him.”Andy Roddick told me that Federer came to Austin, Texas, in 2018 as a personal favor to help him with an event for his charitable foundation, which funds educational programs and activities for lower-income youths. “I pick him up at the airport, we’re driving in, and he’s like, ‘OK, what’s the run of show?’” Roddick said. “And Roger said: ‘Be very specific about what you guys do. I don’t just want to say you help kids, because that’s lazy.’ And then he goes, ‘OK, how can I add the most value to you all today?’ There wasn’t a conversation about ‘What time will I be able to leave? How much time do I have to spend?’”When they arrived at the event, Roddick expected that he would have to be Federer’s escort, introducing him to guests and donors. But Federer acted as if he’d been preparing for the event for weeks. “He breaks away from me and literally goes up to the first two people he sees, introduces himself and works the room by himself, with no agent, no manager running interference,” Roddick said. “I watched him do it for an hour, straight into a room full of strangers and just engaging with people. One of our board members has twins, and they are talking about twins. He’s able to find the parallels and the common ground. I was really impressed by that. The person who needs to do that the least is the best at it. We finished the event, and his plane was delayed, and he walked back into the donor room and started going again. He didn’t get out of Austin until 1 or 2 in the morning, and if he was pissed, no one would have known.”I asked Roddick how unusual that sort of approach was compared with other elite athletes. “The thing I’m most jealous of is not the skill and not the titles — it’s the ease of operation with which Roger exists,” Roddick said. “There are people who are as great as Roger in different sports, but there’s no chance that Jordan or Tiger had the ease of operation Roger has day to day.”Mirka, whom Federer calls his “rock,” has been the key figure in his ability to navigate between his public and private spheres. She has taken on plenty through the years, including bearing and raising two sets of identical twins. Mirka and Roger’s daughters, Charlene and Myla, were born on July 23, 2009, and the family boarded a private jet for Montreal and the Canadian Open three days after Mirka and the newborns checked out of the hospital in Zurich. Their sons, Leo and Lennart, were born on May 6, 2014, leaving just enough time for Roger to make it to the Italian Open. Family logistics have sometimes been daunting — a rotating cast of nannies and a traveling tutor have certainly smoothed some of the bumps — but Mirka’s goal was to turn the road into a home, in part so her husband could play on with peace of mind. “I wasn’t sure if that was what I really wanted for the kids at the beginning, but I must say it keeps us together,” Federer told me in 2015.“I wouldn’t be able to do it,” Roddick told me. “I was a stress ball without family obligations and all that. I needed to have tennis, and now I need to have family and business. I wouldn’t have been able to intertwine all of them.”A few years ago, Roddick asked Federer about the challenges of making all that work, and Federer responded that it was particularly fun when he and his family all shared the same room, as they did one year at the Western & Southern Open outside Cincinnati. Roddick was flabbergasted. “I was like: ‘What do you mean? You all stayed in the same room? Like a bunch of rooms connected?’ And Roger’s like, ‘No, we all had a big room.’ And I’m like: ‘See, that’s the stuff no one else does or can do without losing their minds. That’s not a real thing to stay in a room with four kids and a wife and win a Masters Series event.’”But Federer thrives on compartmentalizing. Paul Annacone, his former coach, remembered Wimbledon in 2011, when Federer lost to Jo‑Wilfried Tsonga in the quarterfinals after blowing a two-set lead for the first time in his career in a Grand Slam singles match. It was, on the surface at least, a devastating moment. “I was thinking: What am I going to say afterwards? How do I figure out the speech?” Annacone told me. “So, he does all his press, and we jump in the car and go back to his house, which is a 30-second ride at Wimbledon, and he literally puts his bags down as we walk in the door and gets down on his hands and knees, and in 30 seconds he’s on the floor with the twins, Myla and Charlene, and they are laughing and giggling and rolling around.”When I traveled with Federer to Chicago in 2018, it was arguably the year of his greatest business coup. Though I didn’t know it yet, Federer was about three months away from signing a 10-year apparel deal with Uniqlo, the Japanese mass-market clothing retailer. The agreement pays Federer $30 million per year even if he retires from competition.It was clearly far more than Nike was prepared to pay an aging superstar, no matter how beloved. Tennis is not a major money-spinner for Nike: It is a small division within the large, global company. Nike is closing in on annual revenue of $45 billion, and “the tennis business is about $350 million, so you do the math,” Nakajima said. The rule of thumb, according to Nakajima, is not to spend more than 10 percent of revenue on athlete sponsorship. Nike was already committed to stars like Serena Williams, Nadal and Sharapova, who had not yet retired. It also had rising stars like Nick Kyrgios, Denis Shapovalov and Amanda Anisimova under contract. To come closer to meeting Federer’s demands, Nakajima said the division would have had to break that 10 percent ceiling.“I’m glad it happened after I left, because I never would have lived with myself,” Nakajima said of the Nike-Federer split. “I mean, are you kidding me? You’re going to let Roger Federer go? It was sad this happened. For me, he’s like a Michael Jordan. He’s already thinking about what’s going to be happening next, and he could potentially be more successful post-career if he does things right. Who wouldn’t want to attach your name to that if you’re a company?”That year, the visit to Chicago felt like a preview not just of the 2018 Laver Cup but also of Federer’s post-competition chapter. He played no competitive tennis during the stopover and acted more like a chief executive than a road-tripping athlete. “Roger is going to have a legacy and a business that is going to live on well past his playing days, similar to a guy like Arnold Palmer in golf,” said John Tobias, a leading tennis agent.Beyond Federer’s lucrative individual pursuits, the Laver Cup has been the primary focus of Team8, the boutique management firm that Federer and Godsick left IMG to form back in 2013. It is an event that, if it prospers, could serve as both a legacy for Federer and a vehicle for him to remain involved in the game as a team captain or organizer. To protect it, he and Godsick pushed insistently behind the scenes for it to become an official part of the A.T.P. Tour, even though it awards no ranking points. They have also fought fiercely to preserve its late-September dates.A big part of Chicago’s appeal to Federer was the chance to play the Laver Cup in the United Center, the home arena of the Bulls. We soon made our way there after landing at Chicago’s Midway International Airport. Federer visited the United Center with Nick Kyrgios, the Australian who would play for the World Team in the Laver Cup but, considering his ambivalence about tennis, would surely have preferred being an N.B.A. star.The highlight was their tour guide: Scottie Pippen, a fine complement to Jordan on those Bulls championship teams. Federer got goosebumps as Pippen escorted them into the Bulls locker room and into the arena. “That was special, meeting Scottie,” Federer told me. “Nick follows basketball now a lot. I still do as well, but way back when Scottie played, that was when I was really following basketball.” The four hours in Chicago felt like an extended fast break, with visits to a deep-dish pizzeria, the Chicago Theater, Millennium Park and the Chicago Athletic Association Hotel for a news conference with Kyrgios; Rod Laver; John McEnroe, the Team World captain; and Mayor Rahm Emanuel. “Roger’s life — if it’s not hectic, it’s not Roger’s life,” Godsick said, “because it’s all he knows.”I joined Federer in the back seat for the car ride to Midway, which would return him to the private jet and his flight to Miami. I asked him if, at this stage of his life, he ever spent time alone. He laughed and seemed surprised by the question. “Not often,” he said. “But I do travel without Mirka and the kids once in a while, and so I’ll get time in my hotel room.” As he saw it, though, he had no particular need for solitude, and he made it clear that he was not yet weary of the travel.“Think about today,” he said. “We left with the sunrise, beautiful weather in Indian Wells, and we get here, and it’s cold and a totally different vibe. That’s the beauty of travel, of seeing different places. I love it. I do. I still love it.”Skipping airport security lines and airline boarding procedures certainly made that attitude easier. The chauffeur drove the car straight onto the tarmac at Midway, stopping right next to the plane. Federer’s first trip to Chicago was ending, but he did get to have one more authentic Chicago experience, as the strong winds made it a genuine struggle for him to open the car door. After winning that battle, he politely bade farewell and fought another gust or two of wind on his way up the boarding stairs before finally ducking inside the jet.My travels with Federer were over, and after writing a column the next day I was soon back in the air in very different style: in a middle seat in economy class on an overbooked American Airlines flight headed for Boston. As I ate dinner on my tray table and shared both armrests with my neighbors, it all seemed like payback — an abrupt reality check after an extended stay in Federer’s low-friction world.Upon arrival at Logan International Airport, I caught a bus north to my town near the New Hampshire border. But I got there past 2 a.m., which meant it was too late to call a local taxi. I ended up walking the three miles home along the side of the road, rolling my suitcase behind me and occasionally laughing out loud in the darkness at the contrast between the glamorous start of my journey and the pedestrian finish. This, it struck me, was the sort of solitude that Roger Federer so rarely experienced.This article is adapted from “The Master: The Long Run and Beautiful Game of Roger Federer,” by Christopher Clarey, published by Twelve on Aug. 24, 2021. More