Soccer is not usually a dangerous subject for Russia’s elite, but Ukraine’s civil war has made Putin very sensitive to whiffs of disloyalty. All the oligarchs who met last month knew that. They were discussing how to avoid his anger, a frightening prospect that none expected in the normally calm course of running the national soccer league. A leaked recording revealed Russia’s most powerful businessmen and officials, each on the board of the Russian Soccer Union, panicked in deciding a seemingly impossible problem: should we admit Crimean soccer teams?

“If there’s a direct order, no question,” said Sergei Galitskii, the billionaire grocery store tycoon. Denying them might make the executives appear opposed to Putin’s annexation of Crimea, in turn inviting Putin’s anger. However admitting the teams to Russian soccer might prompt sanctions from the EU and push FIFA to revoke Russia’s 2018 World Cup bid, also guaranteeing an enraged Putin. Sergei Stepashin, a club owner, said it best: “We’re in checkmate.”

The allusion to chess is telling—Putin strategizes like a chess master, constantly keeping his rivals on edge and using their confusion to cloak grander designs. Stepashin especially should know. He was ousted as prime minister in 1999, replaced by Putin in a palace coup that began Putin’s national political career. Putin, previously the head of Russia’s intelligence agency, was brought in by the ailing president Boris Yeltsin and his advisers to project strength amidst a new war in Chechnya. Foremost among Yeltsin’s inner circle were the oligarchs, Russia’s wealthiest men who hoped to manipulate Putin just as they had Yeltsin for so many years. Putin understood he was living on borrowed time.

He moved quickly to ensure that those who had brought him into power could not take it away from him so easily. As promised, Putin was steely in dealing with Chechnya, effectively leveling Chechnya’s capital Grozny with artillery and garnering massive popularity at home. His popularity ensured that when Putin was put up for election as Russia’s president in 2000, he won by a landslide.

The next step was to secure power from the oligarchs still playing kingmakers in Moscow. Chechnya provided a shield of popularity for his first offensive. After critical media coverage of Putin’s response to the Chechen war, Russia’s two largest television broadcasters were nationalized and their owners forced to flee the country. Both were influential oligarchs, Boris Berezovsky and Vladimir Gusinsky, and both had been part of the circle to bring Putin to power. It was a warning to Putin’s former oligarchic patrons: be loyal or leave.

Muting critical media was essential for Putin’s plan of reconstruction. Under Yeltsin, the state had withered, crime soared, the economy had been ruined, and the oligarchs allowed to become Russia’s real rulers. They had taken some of Russia’s most lucrative companies, and Putin hoped to harness these industries to fund a renaissance of the Russian state. He saw opportunity in Russia’s richest man, Mikhail Khodorkovsky.

Khodorkovsky was an oil and banking magnate, an oligarchic wunderkind who had been one of the first to understand capitalism after the Soviet’s Union’s fall. He built the oil giant Yukos from the carcass of the Soviet oil monopoly, quickly turning it into Russia’s largest, most profitable company. He used the profits to fund his political ambitions, building a network of pro-democracy and philanthropic groups that many said would be the foundation of his presidential bid in 2004.

Yet it was not to be. Khodorkovsky was arrested in 2003 and Yukos was seized by the state, dismembered, and split among Russia’s state energy monopolies. Khodorkovsky had made himself too easy a target—in one move, Putin had taken Russia’s largest oil company, neutralized his most powerful rival, and made clear to the remaining oligarchs that loyalty to the government was their only option.

His brilliance was understanding power in a system with no formal rules, making his strategy a natural fit for the lawless game of international affairs. While Putin was locking up Russia’s richest man, the precursor to today’s Euromaidan protests arrived in Ukraine: the Orange Revolution. Up to a million Ukrainians turned out in 2003 to protest a fraudulent election that had declared the Russian-backed candidate Viktor Yanukovych the winner. The crowd finally forced a new election and the pro-Western candidate Viktor Yuschenko was declared the winner. As Ukraine looked West, Putin saw a chance to put his new acquisitions in the energy to work for Russia, and reel Ukraine back in.

Ukraine was particularly vulnerable because it relied on Russia for all of its natural gas and was the transit point for Russia’s gas pipeline to Europe. Putin used disputes over Ukraine’s gas contract to hound the new pro-Western administration as soon as they took office, constantly threatening to call in Ukrainian debt or suddenly raise gas prices. Russia shut off the pipelines to Ukraine, and to all of Europe, twice, once in 2006 and again in 2009, causing panic internationally and throwing the pro-Western government in Kiev into turmoil.

Soon after the contract dispute began, Ukraine’s prime minister was dismissed, replaced by the pro-Russian candidate Yanukovych. Yanukovych then won the next presidential election, imprisoned the prime minister he replaced, and shortly after taking office, resolved the years-long gas dispute with Russia in Ukraine’s favor effortlessly. The agreement only ran aground when Yanukovych was chased from the country, this time by a second pro-Western uprising, the Euromaidan, which began Ukraine’s current crisis. Putin had learned that Russian energy was an indispensible piece for outwitting Russia’s enemies– first his rivals the oligarchs, then the pro-Western politicians in Kiev, next the West itself.

Putin’s deft use of Russian energy exports neutered the threat of Western sanctions from the beginning. Current sanctions, a patchwork of penalties on Russian companies and businessmen, fail to cover any sector of the Russian economy comprehensively, most notably the energy industry. Although pressure has been building, European governments worry that they’ll have cold voters come winter, just like in 2006, and no guarantee of progress in Ukraine. Without European cooperation, the U.S. has remained unwilling to support Ukraine substantively on it own, preferring instead to prepare NATO for the next possible threat from Russia. The failure of any grand Western coalition in Ukraine hung from the lynchpin of Putin’s pipelines.

Isolating Ukraine from Western allies is ideal for Putin. Alone, Ukraine cannot negotiate, only persist or give in to Putin’s demands. For now, it looks more like the latter. If Putin can force Kiev to sign a peace agreement that gives greater authority to Ukraine’s East, he sanctifies his goal of a Russian-influenced Ukraine in international law. Regardless of Putin’s critics, he has single-mindedly pursued Russia’s national interests in Ukraine, strategically deploying Russian power to outmaneuver his rivals and is near achieving his goals. It is a feat no Western leader can claim.

In the meantime, no other factor really matters. Not sanctions, not Ukrainian civil war, not the downing of a civilian aircraft—all of it is fundamentally irrelevant to Putin’s basic understanding how to beat the West in the contest for Ukraine’s future. Putin’s battle against the oligarchs yielded control of Russian energy and a mastery of corrupt politics, together giving him an insurmountable insurance policy in Ukraine. If Western leaders remain unable to best this strategy and deal with Putin on equal terms, they will fare like the oligarchs—huddled together in panic, wondering what it is that Putin wants.