He runs Chelsea like a benevolent Rasputin: there’s no disputin’ the magical spell cast by Roman Abramovich.

Roman Abramovich is going to have a busy few months. Even with the arrival of Antonio Conte, hired to replace the 69-year-old caretaker Guus Hiddink, he needs to rebuild Chelsea into a top team again. Where will he begin? How will he go about it? How, exactly, does Roman Abramovich run his club?

Few people know. The $10 billion man tends to avoid speaking much, partly by pretending to know little English. All his bodyguards, pilots, yacht attendants, and various servants, are sworn to silence. People at Chelsea tend to refer to him only as “the owner” or “Mr. A.” But over the years, by talking with Chelsea officials and coaches and by scouring the memoirs of football people in his orbit, I have gradually put together a picture of one of the most fascinating club owners in the world.

Before Abramovich decided to buy a club, he had a look around Spain and Italy. Ownership there seemed unduly complicated. In Italy, many of the families who owned clubs had been doing business with each other for generations. In Spain, horror of horrors, the fans themselves owned the biggest clubs. As for the Bundesliga, Abramovich never seems to have considered it.

In April 2002 he flew to Manchester to watch United. After the game, Dominic Midgley and Chris Hutchins write in their biography Abramovich (2004), Rio Ferdinand drove him to Manchester airport, and the Russian charmed the player by joining in a sing-along with a fellow passenger, Ferdinand’s 4-year-old half-brother. (Charm is one of the secrets of Abramovich’s success.)

Not long after that, the story goes, Abramovich was flying in a helicopter over London when he spotted a stadium handily located near his house in Knightsbridge. “What’s that?” he reportedly asked. It was Chelsea. He bought the club for about £60 million, sealing the deal with the departing owner Ken Bates over a bottle of Evian water in London’s Dorchester Hotel. (Another secret of his success: He rarely drinks.)

Back then, the Russian still talked to journalists. When my newspaper, the Financial Times, rang to ask about his purchase, he revealed that his favorite player was Arsenal striker Thierry Henry and explained why he had bought Chelsea: “I’m looking at it as something to have fun with rather than having to realize a return. I don’t look at this as a financial investment.” He has barely spoken another word in public since.

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Abramovich was born in Saratov in northern Russia on Oct. 24, 1966. By age 2 he had lost both parents: his mother, Irina, to complications of a botched abortion, and his father, Arkady, in a crane accident. Growing up as a short Jewish orphan in the anti-Semitic Soviet Union shaped the boy: He learned to be acutely sensitive to other people’s desires. All his life he has approached others with a disarming smile. Nobody who has met him seems ever to have considered him outwardly nasty.

The toddler was adopted by his father’s brother, Leib, who lived in Ukhta, a town created by former political prisoners 700 miles northeast of Moscow. Leib ran the supplies department at a state-owned timber business. He was what Russians call a nesun, a “carrier”: one who carries off bits of state property from the workplace—in Leib’s case to sell them on the black market.

Never a brilliant pupil, the young Abramovich became a gifted wheeler-dealer. By the late 1980s the USSR under Mikhail Gorbachev had opened a space for entrepreneurs. Abramovich sold dolls in an open-air market in Moscow and dealt in everything from tires to bodyguards to cigarettes. But all this was small time. His first big break seems to have been in oil: He bought it at cheap Soviet prices, and procured an export license to sell it at a big profit abroad.

The longtime Chelsea midfielder Frank Lampard writes in his autobiography, Totally Frank: “I don’t know the exact details of his background but from what I have read Mr. Abramovich had a very humble start in life and has made his own luck.” In fact, “luck” in Russia depends on proximity to power. Abramovich achieved that by charming the oligarch Boris Berezhovsky, who was close to the ruling Yeltsin family. Years later, after the two men had fallen out, Berezhovsky would say that of all the businessmen he had encountered, Abramovich was best at “person-to-person relations.”

In 1995 Berezhovsky and the 29-year-old Abramovich bought 51% of the state-owned Sibneft (“Siberian oil”) company. They paid less than $200 million for it. Given the wealth under the Siberian earth, this was possibly the biggest act of nesun in Russian history. The two men soon increased their stake in Sibneft by dubious dilutions of other investors’ shares.

Even after Vladimir Putin succeeded Yeltsin as president in 1999, Abramovich stuck close to power. Indeed, Midgley and Hutchins report that he helped interview candidates for Putin’s first cabinet. He also helped create and finance Putin’s electoral vehicle, the United Russia party. And, presumably to please Putin, he spent several years as governor of the dirt-poor Chukhotka region in Siberia, giving personal gifts to the local Eskimos. But Abramovich always had his eye on the main chance: Chukhotka offered little-known tax perks.

In 2000 Putin assembled the oligarchs in the Kremlin and gave them a warning: They could keep their wealth as long as they stayed out of politics. Some oligarchs—notably Berezhovsky and Mikhail Khodorkovsky—didn’t get the message at once, but Abramovich did. He began selling off his Russian holdings, and then bought the debt-ridden Chelsea.

Many Russians initially resented what they saw as an unpatriotic investment, funded by money ripped off from them. Moscow’s mayor Yuri Luzhkov accused Abramovich of “spitting on his homeland.” The oligarch soon responded by putting some of Sibneft’s money into CSKA Moscow, creating a Russian national football academy, and hiring Guus Hiddink to coach the national team. Abramovich isn’t one of those early 1990s New Russians who had their opponents gunned down. His instinct is to buy them off.

In 2003 he was the richest man ever to take over a football club. There has been endless speculation as to why he did so. Some said Chelsea was his stepping stone to a political career. Others said he wanted to become famous in Britain, as an insurance policy in case Putin ever requested his extradition.

The most convincing explanation I have heard comes from Derk Sauer, a little Dutchman who became a media mogul in Moscow, chiefly by creating Russian versions of publications like Playboy and Cosmopolitan. Sauer lives in a posh suburb of Moscow, where one of his sons played football with one of Abramovich’s, and he is a longtime student of the oligarch tribe.

Sauer’s stable used to include an obscure football magazine. “A very nice magazine, but it just wasn’t selling,” he told me over breakfast in Amsterdam in 2005. One day somebody phoned offering to buy it. Sauer discovered that the ultimate buyer was Abramovich. “It was his favorite magazine, his bible,” marvels Sauer. “One of our reporters went to Chelsea to interview him, and Abramovich opened a cupboard and there were all these issues of the magazine. Typical Abramovich: He just wanted to have it.”

That, said Sauer, was also why Abramovich bought Chelsea. “These people [Russian oligarchs] have money but they don’t have status, so what do you do? You try to acquire status. In 1920s America there were tycoons who did exactly the same. They bought newspapers, went into art, that sort of thing. Now the Russians are all trying to get out of business. For a lot of the oligarchs, it’s over. They’ll lose their companies one way or another. So they’re trying to get as much money out as possible and then put it into soccer.” In short, Chelsea was not some cunning Abramovich venture; it was an insurance policy, and a retirement hobby for a lifelong football fan.

In 2005, after effectively ousting Berezhovsky, Abramovich sold his stake in Sibneft to the state oil company, Gazprom, for $13 billion—over 65 times what they had paid for it.

Abramovich started at Chelsea painfully aware of his big handicap: He knew no more about football than the average fan. He wanted an attacking team full of big stars, but he wasn’t sure that football was as simple as that. And so he displayed another secret of his success: He is a good listener. Despite being the master of all he surveyed at a historically mediocre club, initially he barely opened his mouth.

He let Claudio Ranieri, the manager he had inherited, stay on for his first year. Then, in 2004, he hired his dream coach, José Mourinho, and handed him a list of stars. Who did Mourinho want? None, said Mourinho. Abramovich was disappointed, but he let the Portuguese (who prefers to be the biggest star on the club) have his way. Having a small ego himself, Abramovich can work with large personalities. Mourinho rewarded him with two straight league titles, Chelsea’s first in 50 years.

Abramovich knew that football men like Mourinho would try to keep him in his box by hinting that he didn’t know the game. Without football knowledge, Abramovich would also be easy prey for agents (especially Mourinho’s de facto house agent, Jorge Mendes) trying to sell him players. Abramovich therefore needed to acquire knowledge independently. An admirer of Dutch football, he hired the aged Dutch scout Piet de Visser as a private teacher.

For years they traveled around Europe together, sometimes watching as many as three games in a day. De Visser describes their cooperation in his biography, Voetbal als medicijn (“Football as Medicine”), written by Willem Vissers. (“I know that Mr. Roman doesn’t really want me to talk about him in my biography,” de Visser admits. “But I am 80 now, and I think it must be possible.”)

De Visser had almost no stomach left after innumerable illnesses, and so Abramovich ordered the chef on his yacht to strain the scout’s food. Touched, de Visser told him, “I scout you another Ronaldo [the Brazilian] before I die.” In the biography, he describes following Euro 2004 from Abramovich’s yacht moored off the coast at Lisbon: “In the morning on the boat, Mr. Roman would often knock on the door of my room. He wanted to watch replays of games or match situations with me … I had to explain certain images. He was a quick pupil. Never have I seen a man with so much intellect and such pure love of football. After about four years, he said, ‘Piet, thank you. Now I know enough.’ ”

Abramovich also sought advice from Chelsea players. Lampard says in his autobiography, “Outside the manager, John [Terry] and I have probably the closest relationship with Roman. We speak to him sometimes just minutes after a game to discuss how it went and at other times when he wants to gauge our views on specific subjects … Abramovich is also very like Mourinho in his thirst to discover the reasons behind a certain event or result.” As a typical British footballer, Lampard was wary of speaking out, but Abramovich encouraged him to. After all, he needed independent sources of information within Chelsea. And if Lampard mentioned a teammate’s particular technical shortcoming, Abramovich would say, “So why don’t you tell him?”

Lampard professes to revere Abramovich, and I suspect this regard is genuine. People in football are generally impressed by money and unbothered by its provenance. Lampard describes the holiday his family took on one of Abramovich’s yachts and recounts the time the oligarch bought “pots of the finest Russian caviar” to the players’ hotel: “I love the stuff and was tucking in while most of the lads looked at me strangely. I reckon they were worth about five grand a pot.”

Football people also tend to appreciate Abramovich’s apparently friendly humility, the way he visits the changing room after a game to shake players’ hands but without acting bossy. Describing his first meeting with Abramovich, Hiddink called him a “very quiet man. No urge at all to profile himself. Not: ‘Look how important I am, what I have and what I can do.’ It was even below … Jeans and a very normal watch. Even less than normal.”

Gradually, though, Abramovich has quietly asserted himself at Chelsea. As Lampard says, “Here is a man who will not take any shit or excuses.” Tired of Mourinho’s refusal to buy stars, Abramovich went and signed Shevchenko and Michael Ballack himself. One Chelsea official told me that the disastrous signing of Fernando Torres for £50 million from Liverpool in 2011 was also Abramovich-led. The official said Chelsea’s technocrats had to give the owner his way once or twice in order to teach him that buying stars wasn’t always the answer.

When Chelsea officials talk about Abramovich, they sometimes describe him as a promising student. Frank Arnesen, the Dane who was for a time Chelsea’s technical director, once tried to explain to Abramovich the value of the Ivorian bit player Salomon Kalou. The forward lacked the star quality that Abramovich craved. But, argued Arnesen, if you took into account Kalou’s relatively low salary and low transfer fee, and the number of games in which he appeared and did something useful, he might actually be Chelsea’s most valuable player per pound spent. One imagines Abramovich being unimpressed.

Abramovich’s growing interventionism shows in his willingness to cull managers. Hiddink is his ninth in eight years. This evokes the stereotype of the impatient New Russian for whom life is a shopping trip. In fact, though, hiring and firing is not Abramovich’s instinct. His preferred mode is to be loyal to his people. Even when sacking Mourinho the first time around, he gave him a rare 612 Scaglietti Ferrari as a goodbye present. The second time he kept him on longer than many owners would have.

Abramovich likes to work long-term with a small court of employees: people like de Visser or Abramovich’s Canadian-Russian right-hand man, Eugene Tenenbaum, with whom he mixes business with pleasure. If Abramovich never spontaneously invites you to fly with him from London to Saint-Tropez to hang out on his yacht (currently the Eclipse, at 162 meters the world’s second-longest), you aren’t a member of the court where decisions get made.

This court is particularly influential because Abramovich doesn’t do everyday management himself. He is too busy traveling: Arguably his primary residence is in Moscow, and he is also often on the Eclipse. People at Chelsea rarely see him. Instead, his will tends to be transmitted by courtiers. A Chelsea director once told me that they would often come to him and say, “Do this, this is what he wants.” Whereupon the director would wonder, Does he really want this?

One thing Abramovich desperately does want is for Chelsea to play appealing football. Carlo Ancelotti, hired to coach Chelsea in 2009, told me years later, “The first time I met Roman Abramovich, he said, ‘When I see Chelsea I don’t recognize it is Chelsea—the identity, the style of play.’ ” Ancelotti won the English Double at Chelsea, but he didn’t last long either.

Lately, beneath the blizzard of managerial sackings, Chelsea has settled down. The lines of command have become clearer. Probably uniquely in professional football, the club’s two most powerful executives (besides the coach) are a woman and a black man: the multilingual Russian-Canadian director, Marina Granovskaia (Abramovich’s former personal assistant), and the Nigerian technical director, Michael Emenalo.

Abramovich deserves credit for bucking football’s traditional racism and sexism. (Similarly, his longtime spokesman in Russia, John Mann, is a black American.) It’s also smart to look beyond the overfished white male talent pool. But calculations of power probably also underlie his choices. Given football’s instinctive discrimination, Granovskaia and Emenalo might not get hired by other clubs. That makes them more loyal to, and dependent on, Abramovich.

The trio cooperates smoothly. Mike Forde, Chelsea’s director of football operations from 2007 through 2013, told me, “I think it’s a brilliant dynamic now. You’ve got a very experienced football owner who has learned, who understands the market, who is very bright.” When Abramovich rehired Mourinho in 2013, they were like a middle-aged couple reuniting after some hard life lessons. They renegotiated their relationship. Abramovich accepted that Mourinho would have the last say on the big decisions. No longer would the owner impose purchases of stars. Mourinho, in turn, accepted that he would have to share decision-making with Abramovich’s courtiers.

That new order stopped working this season. It wasn’t just Mourinho’s fault. It is harder now for a sugar daddy to buy titles than it was back in 2003, because football is finally achieving cost control. Much attention has gone to UEFA’s “financial fair play” rules, which aim to stop clubs spending more than their revenue. In fact, FFP hasn’t bitten very hard: Clubs like Paris Saint-Germain and Manchester City have stood up pretty successfully to UEFA.

However, national versions of FFP are more effective. The English and Spanish leagues have followed the German and French examples of limiting clubs’ spending. That means an owner like Abramovich can no longer splash what he likes to buy the best players. Chelsea’s net spend on transfers since 2013 is only about £85 million—far less than certain rivals. Chelsea paid a lot for Hazard and Pedro but got a lot for David Luiz and Romelu Lukaku. One reason Mourinho kept playing his first-choice 11 until they were worn into the ground is that his second-choice players were much worse. Chelsea today aren’t free to pay for a squad of 22 world-class players the way they were a decade ago.

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When Abramovich looks back, he must be happy with his purchase of Chelsea. In 2003 “You can’t buy a winning team” was still a football maxim. Abramovich’s Chelsea has since won four league titles and the Champions League. True, success has cost him more than expected. Like countless businessmen who bought into football before him, he fondly imagined that he would be the first man to run a club as a profit-making enterprise. That didn’t happen, but given what a tiny industry football is compared with oil, that won’t have bothered him much. Abramovich has sunk perhaps £1 billion into Chelsea since 2003. Yet according to the Sunday Times Rich List, he is still Britain’s tenth wealthiest man, with a fortune of £7.29 billion. Abramovich can buy Didier Drogba or Eden Hazard with about as much concern as the rest of us buy lunch. And he’s had fun.

Moreover, a London-based football club is exactly the hobby he needed for the Putin era. His bet on abandoning his Russian businesses has proved correct: Putin and his friends from the security forces have seized the commanding heights of Russia’s economy for themselves, and though Abramovich still loves Moscow, it must be more comfortable to contemplate the process from a safe distance.

His seven children by three wives are mostly making their lives in the U.K. His current wife, Dasha Zhukhova, amuses herself collecting art (as did the previous incumbent, Irina Malandina, who walked away from the divorce with about £1 billion). Abramovich still dabbles in investments—everything from nickel to green energy—but does nothing likely to change his financial position drastically. His old partner Berezhovsky filed a $6.5 billion lawsuit against him claiming that Abramovich had ripped him off over Sibneft, but Abramovich won the case and Berezhovsky later killed himself. Granted, Abramovich is forever surrounded by bodyguards, which must get irritating, but for an orphan who got rich amid the assassinations in 1990s Moscow, life must seem pretty good.

One day he may get bored, or even die (though the high-end anti-aging industry is making good progress). Doomsayers used to talk about what would happen to Chelsea once he checked out. The implication was that his heirs might ask Chelsea to repay the money he had put into the club, whereupon Chelsea would be in deep trouble.

That wouldn’t be true today. For one thing, Abramovich has lodged the debt of about £1 billion that club owes him with Chelsea’s holding company Fordstam Ltd. The money is repayable at 18 months’ notice. If Abramovich or his heirs ever demanded repayment, Chelsea could simply declare Fordstam bankrupt and create a new debt-free holding company for the club—a common dodge in football.

If Abramovich’s heirs ever wanted their money back, they could just sell the club. In December, Chinese investors bought a 13% stake in Manchester City for £265 million, valuing the club at £2 billion in total. Let’s say Chelsea is worth the same as City (although they are probably worth more, given that they own big real estate in hyper-priced west London). If the Abramovich family sold Chelsea for £2 billion and then repaid themselves the £1 billion they have lent the club, the family would make a profit of £1 billion— more than 11 times what Abramovich paid for Chelsea in 2003, adjusted for inflation.

Small wonder that on the oligarch’s face, glimpsed by mortals only in the stadium on match days, you will usually see that pleasant, cryptic, wordless smile.