In the spring of 2014, President Vladimir Putin delivered an address in St. George Hall, a chandeliered ballroom in the Kremlin, to celebrate the annexation of the Crimean Peninsula. “Crimea has always been an integral part of Russia in the hearts and minds of our people,” he declared, to a standing ovation. Despite Putin’s triumphal language, the annexation presented Russia with a formidable logistical challenge: Crimea’s physical isolation. Crimea, which is roughly the size of Massachusetts, is a landscape of sandy beaches and verdant mountains that juts into the Black Sea. It’s connected to Ukraine by a narrow isthmus to the north but is separated from Russia by a stretch of water called the Kerch Strait. Ukraine, to which Crimea had belonged, viewed Russia’s occupation as illegal, and had sealed off access to the peninsula, closing the single road to commercial traffic and shutting down the rail lines.

In response, Putin convened a council of engineers, construction experts, and government officials to look at options for connecting Crimea to the Russian mainland. They considered more than ninety possibilities, including an undersea tunnel, before deciding to build a bridge. The Russian state is notoriously inefficient at following through on the quotidian details of government administration; its more natural mode is building projects of tremendous scale. In keeping with this tradition of expanse, and expense, the bridge would span nearly twelve miles, making it the longest in the country, and would cost more than three billion dollars. When completed, it would symbolically cement Russia’s control over the territory and demonstrate the country’s reëmergence as a geopolitical power willing to challenge the post-Cold War order.

The bridge would be a demanding and technically complex project, however, and at first there were doubts about who would be willing to undertake it. Then, in January, 2015, the Russian government announced that Arkady Rotenberg, a sixty-three-year-old magnate with interests in construction, banking, transportation, and energy, would direct the project. In retrospect, the choice was obvious, almost inevitable. Rotenberg’s personal wealth is estimated at more than two and a half billion dollars, and the bulk of his income derives from state contracts, mostly to build thousands of miles of roads and natural-gas pipelines and other infrastructure projects. Last year, the Russian edition of Forbes dubbed Rotenberg “the king of state orders” for winning nine billion dollars’ worth of government contracts in 2015 alone, more than any other Russian businessman. But perhaps the most salient detail in Rotenberg’s biography dates from childhood: in 1963, at the age of twelve, he joined the same judo club as Putin. The two became sparring partners and friends, and have remained close ever since.

Rotenberg’s success is a prime example of a political and economic restructuring that has taken place during Putin’s seventeen years in office: the de-fanging of one oligarchic class and the creation of another. In the nineties, a coterie of business figures built corporate empires that had little loyalty to the state. Under Putin, they were co-opted, marginalized, or strong-armed into obedience. The 2003 arrest, and subsequent conviction, of Mikhail Khodorkovsky, the head of the Yukos oil company, brought home the point. At the same time, a new caste of oligarchs emerged, many with close personal ties to Putin. These oligarchs have been allowed to extract vast wealth from the state, often through lucrative government contracts, while understanding that their ultimate duty is to serve the President and shore up the system over which he rules.

The Crimean bridge is different from many of Rotenberg’s other state ventures, in that he is not expected to make much money from it. “This project is not about profits,” one banker in Moscow, who specializes in transportation and infrastructure, told me. He was matter-of-fact about how Rotenberg ended up in charge: “The bridge had to be built, and everyone else was refusing. It was the only possible solution.”

Construction began last year. Rotenberg, who has a reputation as an informed, hands-on manager, visits every few months, passing above the site in his helicopter before inspecting the project with a retinue of engineers and road-building specialists. Last fall, a correspondent from Russian state television filmed a fawning news segment about the bridge. Strolling with Rotenberg along one of the few completed sections, the host invoked the bridge’s reputation as “the construction project of the century.” The two put on hard hats and surveyed the jumble of cranes and excavators and drills in motion around them.

Rotenberg has the squat and powerful frame of a wrestler, and a round, impish face. His speech is clipped and straightforward, and he does not appear to enjoy introspection. But, when the television host pressed him to offer up platitudes on the bridge, Rotenberg did his best to oblige. “Besides financial profit—which, for a business, is a sign of success, of course—I also want the project to mean something for future generations,” he said. What Russians make of the bridge will be clear soon enough; the first cars will pass over it later this year. But its significance for Rotenberg already seems apparent. It is a totem of his service to the state and to its leader, Putin—and of their friendship, which has thrived at the intersection of state politics and big business.

Rotenberg was born in 1951 in Leningrad, a city deeply scarred by the Nazis’ two-and-a-half-year blockade during the Second World War. Rotenberg’s father, Roman, was a deputy director at the Red Dawn telephone factory, and his position gave the family a measure of stability and comfort. They lived in their own apartment, not a communal apartment like many families, including Putin’s. When Arkady was twelve, against his initial protests, his father took him to train with Anatoly Rakhlin, one of Leningrad’s better-known practitioners of sambo, a Soviet martial art that borrows from judo and was developed by Red Army officers in the nineteen-twenties. In a chaotic city, Rakhlin’s class offered teen-agers a redoubt of discipline. Putin, who was also in the class, said, in “First Person,” a book-length interview published during his first Presidential campaign, in 2000, that the training played a decisive role in his life. “Judo is not just a sport,” Putin said. “It’s a philosophy. It’s respect for your elders and for your opponent. It’s not for weaklings. . . . You come out onto the mat, you bow to one another, you follow ritual.”

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Rotenberg and Putin grew close travelling around Leningrad, and soon around the whole of the Soviet Union, for competitions. Nikolay Vaschilin, a retired K.G.B. officer who trained with them, remembers that the two were fond of pranks. (Putin later described himself during those years as “a troublemaker.”) One time, Vaschilin told me, the boys ran out of an alleyway during a May Day parade and threw wire pellets at balloons carried by the marchers, surprising them with a fusillade of pops. Another friend from that time recalled that he and Rotenberg would pilfer candy and other food from younger children at sports camps by sneaking up on them in the toilets, where kids would go to hide their treats from other boys: “They were immediately frightened and would give us a little something,” he said.