Twenty years before Vladimir Putin began his ingenious campaign to influence the U.S. presidential election, his predecessor as Russia’s president stood on a dark street near the White House. In his underpants. Looking for a pizza.

It was September 1994, and Boris Yeltsin was in Washington for a state visit with his new friend, President Bill Clinton. The Soviet Union had collapsed just three years earlier, and a relationship was blossoming between the U.S. and Russia, one that held the promise of burying decades of hostility. Russia’s abrupt transition from communist dictatorship was chaotic, but a fragile democratic process and nascent capitalism were taking hold. U.S. officials entertained visions of a Western-friendly Russia as a partner in a stable and secure Europe. To that end, Clinton and Yeltsin had built an alliance on the shared goal of preventing a revanchist security state from taking power in Moscow and returning the U.S. and Russia to a Cold War state of hostility. During one early visit to Moscow, Clinton told a young audience to “choose hope over fear" and "find a new definition of Russia’s greatness."


Rarely had an American and a Russian leader been so chummy. Clinton and Yeltsin were buddies, two lovable rascals with big appetites. But something else was different as well: For the first time in decades, Russia was the obvious number two in the relationship. Stripped of its Iron Curtain puppet states, its economy in tatters and its military breaking down, Russia was a shrinking, messy place. And its president was becoming an embarrassment. A presumed alcoholic, Yeltsin would often lose his balance in public, sending aides scurrying to prop him back up. In one slurred telephone conversation with Clinton, the Russian proposed that the men hold a secret meeting on a submarine.

But nothing could top that fall night in 1994. While staying at Blair House—the guest residence for visiting foreign dignitaries across Pennsylvania Avenue from the White House—Yeltsin slipped past his security, stumbled down the stairs and stepped onto the street. “Pizza! Pizza!” he blurted at the Secret Service agents who intercepted him. (There are two versions of the story: In one that Clinton himself told to a biographer, Yeltsin is on the street; in another, he's stopped before he makes it out the door.)

The next day, Clinton and Yeltsin had a long and friendly meeting. Their fates were connected: Clinton wanted a friendly and stable Russia as a foreign policy success story. Yeltsin needed American money to avoid a total economic collapse. When Clinton raised plans to expand the NATO alliance into eastern Europe, Yeltsin didn’t object. The men even agreed that Russia itself might one day join NATO—a concept that seems downright ludicrous today, as Putin threatens the alliance with nuclear exercises. At a press conference afterwards, the two men clowned around. Yeltsin was in an antic state that one White House aide dubbed “high jabberwocky,” while Clinton himself doubled over with laughter at his Russian friend’s playfulness.

Looking back today, the scene is infused with almost unbelievable optimism: the idea that the U.S. and Russia could be military allies, with one helping the other to grow an open and truly democratic society.

But for one man in Russia, it symbolized a profound humiliation. Vladimir Putin was then a minor public official, serving as a deputy city functionary in St. Petersburg after ending his career as a KGB agent, withdrawn from East Germany after its communist government fell. The notion that the Soviet state in which he’d been raised and trained, whose demise he once called “the greatest geopolitical catastrophe of the century,” had become a client state with a leader who was a source of Western amusement was stinging. It was a sting he never forgot, and when Putin met with Russian troops shortly after he took power on the first day of the new millennium, January 1, 2000, he told them their mission included “restoring Russia’s honor and dignity.”

“He sees the 1990’s as one long period of humiliation—domestically and internationally,” says James Goldgeier, dean of the School of International Service at American University and a former top Russia official on Clinton’s national security staff. “From Putin’s standpoint, the ‘Bill and Boris show’ was basically Boris saying yes to everything Bill wanted—and that was the U.S. basically defining the order of the world and what Russia’s place in it could be, and that Russia was too weak to do anything but go along.”

“Putin sees the 1990s as one long period of humiliation, domestically and internationally,” says James Goldgeier, dean of the School of International Service at American University and former top official on Clinton’s national security staff. Above, MiG fighter jets are shown stripped of mechanical parts and abandoned on a highway on the outskirts of Leningrad, USSR, in May 1990. | Getty

Yeltsin’s drunkenness symbolized the self-loathing shambles to which the former superpower had been reduced. Russia was a defeated nation. It had lost the Cold War, and along with it millions of square miles of territory, as imperial possessions dating to the czarist era declared their independence. The country’s economy collapsed, impoverishing most everyone except the insiders who looted public assets. Alcoholism and prostitution boomed. Life expectancy shrank.

Meanwhile, America’s influence only grew. Bill Clinton began an eastward expansion of NATO and bombed the former Yugoslavia. American economic experts flew to Moscow to provide advice on democracy and economics, pressing for “shock therapy” in the Russian economy that delivered painful jolts but little gain. Clinton even did his best to influence Russian politics, throwing his support to a deeply unpopular Yeltsin, who used his ties to the U.S.—and its economic aid—to narrowly escape political defeat in 1996.

Today, as the U.S. grapples with a Russia with resurgent global ambitions, with a Kremlin that hacks our emails, manipulates our news—and, according to the CIA, actively worked to elect Donald Trump—it’s important to realize that for Putin, it’s not just a constant move for advantage. Yes, Putin is pressing Russia’s current interests. But in scheming to defeat Hillary Clinton, and by subjecting American democracy itself to Russian influence, he is also closing a loop opened in part by the Clintons 20 years ago. Putin can’t undo Russia’s Cold War defeat by America. But he can avenge it. And in Donald Trump—the man who defeated Hillary Clinton and seems ready to deal with Putin on terms that few other American politicians would countenance—he hopes he has found a willing partner.

Says Strobe Talbott, a Russia specialist who served as deputy secretary of state under Bill Clinton: “He basically wants to make Russia great again.”

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Yeltsin’s ramshackle rule lasted until the end of the 1990s—a period in which Russia both endured a massive financial crisis and saw the rise of a dominant new class of oligarchs who had plundered the nation’s assets. (They included many of Putin’s friends, and, some allege, the future president himself.) America’s experience stood in acute contrast. During the '90s the U.S. enjoyed an economic boom, while emerging as the world’s lone superpower after two successful NATO interventions in the Balkans, which left Washington enchanted with its own military might.

On New Year’s Eve 1999, Yeltsin—battered by booze, multiple heart attacks and semi-open rebellion by a Russian military furious over NATO’s muscle-flexing—abruptly resigned. He appointed Putin, who had served until the previous August as head of the KGB’s successor organization, to succeed him as president. Bolstered by his lead role in a popular crackdown on alleged terrorists in the Russian republic of Chechnya, Putin was narrowly elected the following March.

Putin didn’t challenge the U.S. right away. In 2000 Russia was too weak for a return to confrontation, its military still a hollow shell, and distracted by the brutal Chechnya campaign. In fact he and George W. Bush got off to a chummy start, with the president famously declaring after their first meeting in June 2001 that he looked into Putin’s eyes and was “able to get a sense of his soul.” After the September 11, 2001, attacks, Putin was the first world leader to call George W. Bush, with whom he hoped to partner against Islamic terrorism—Putin’s label for what others called a Chechen independence movement.

The Bush-Putin relationship deteriorated for many reasons. But one of them, ironically, was a charge of election interference. Putin was furious when Washington backed a popular, pro-Western movement challenging the outcome of Ukraine’s 2004 presidential election. He lashed out at what he called U.S. interference in a former Soviet republic that had long been a possession of the Russian empire. The U.S. was pursuing a “dictatorship of international affairs,” Putin said, disguised with “beautiful pseudo-democratic phraseology.”

Putin saw another kind of political agenda in the former Soviet republic of Georgia, with which he did battle over a territorial dispute in August 2008. In a television interview he implied that the Bush administration had goaded Georgia’s Western-friendly government into a fight.

“The suspicion would arise that someone in the United States created this conflict on purpose to stir up the situation and to create an advantage for one of the candidates in the competitive race for the presidency in the United States,” Putin told CNN at the time. “They needed a small victorious war.”

Some Russia experts and U.S. officials call Putin’s increasingly public grievances about America a contrivance — a narrative to support what the Russian-born journalist Arkady Ostrovsky, in his recent book The Invention of Russia, calls Putin’s “restoration ideology.” By this line of thinking, Putin has sold nationalism and militarism to his public to cover for a weak economy highly vulnerable to fluctuations in the price of its oil exports. It was this atmosphere of hostility that a newly elected Barack Obama sought to cool with his Russia “reset,” a mission led by his secretary of state: Hillary Clinton. Whatever Clinton thought she might accomplish, she couldn’t have imagined what it would eventually mean for her own political future.

A column of Russian armored vehicles moves towards the Roki tunnel on the border with Russia as they leave the Georgian region of South Ossetia on August 23, 2008. | Getty

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Joining her husband for his first state visit to Russia in January 1994, Hillary Clinton had a bumpy flight into Moscow. As her motorcade hurtled into the city, Clinton felt queasy, and searched in vain for an improvised barf bag in her limousine. No dice. “I bent my head over,” she later recalled in her memoir Living History, “and threw up on the floor.”

On a personal level, though, Clinton got off on the right foot. She, too, bonded with Yeltsin—who, somewhat oddly, told her at one dinner that he kept a photo of the first lady in his office that he looked at “every day.” During her years in the Senate, Clinton—preoccupied like most of Washington by Iraq and terrorism—spent little time thinking about Russia. During one 2008 primary debate with Obama she struggled to pronounce the name of the country’s new president, Dmitry Medvedev, adding an embarrassed “whatever” afterwards.

Once she took the job of secretary of state in 2009, Clinton was charged with Obama’s “reset” policy, which sought common ground with Russia as a step toward melting the frost that had settled over the relationship in the late Bush era. Issues like nuclear arms control and a stable Afghanistan could be the building blocks of a new and stronger relationship, the thinking went. Obama’s optimism was based in part on the fact that the relatively moderate Medvedev had succeeded Putin—forced by a term-limits law to surrender the presidency. Putin, however, assumed the job of prime minister and retained far more behind-the-scenes power than U.S. officials had anticipated.

As secretary of state, Clinton played into Putin’s long-held anxieties about the U.S.—all of which were echoes of the American policies launched during her husband’s presidency, and the boozy Bill-and-Boris show of the 1990s.

One was Putin’s belief that America blithely staged military interventions around the world with little regard for international—or at least Russian—opinion. Hillary Clinton had been a supporter of the 2003 Iraq War and Obama’s 2011 intervention in Libya. Putin opposed both those campaigns—and, as a paranoid autocrat, particularly resented Washington’s record of regime-change policies. It didn’t help that the Clinton name already reminded Russian officials of the 1990s U.S.-led NATO interventions in the Balkans, which many hardliners considered to be outrageous Western aggression against their Slavic brothers.

Related was Hillary Clinton’s enthusiasm for NATO’s further expansion into Eastern Europe. That process was based on the well-founded idea that Eastern Europe needed—indeed, was asking for—protection from Russia aggression. But Russia’s military establishment treated it as a slow-rolling invasion of their sphere of influence.

This reaction, too, had its roots under Bill Clinton. An expanded NATO would help ensure democracy, prosperity and stability across Europe, he believed. Moscow took a sharply different view. After one 1994 summit at which Yeltsin gave Bill Clinton his blessing to the addition of new NATO members—including Poland and Hungary, both former Soviet satellites—a communist newspaper fumed about “the capitulation of Russian policy before NATO and the U.S.” One of Yeltsin’s main political opponents said he had allowed “his friend Bill [to] kick him in the rear.” He compared the agreement to the treatment of Germany at Versailles after World War I—a recurring theme among Russian officials since the Cold War’s end.

Some of Bill Clinton’s top advisers correctly predicted that NATO expansion would produce a backlash in Moscow, and would create a handy narrative for would-be nationalists to posture against the West. Clinton’s secretary of defense, William Perry, told POLITICO this summer that he considered resigning over the issue out of concern for its effect on U.S.-Russia relations. But Clinton pressed ahead, kicking off a process that added a dozen new members over the next 20 years, from the Baltic countries of Latvia, Lithuania and Estonia through Eastern Europe (the Czech Republic and Romania) and into the former Yugoslavia—all places where Russia had once enjoyed uncontested influence.

As Obama kept the NATO train rolling, his secretary of state was fully on board. “There can be no question that NATO will continue to keep its doors open to new members,” Clinton said in February 2010.

Whatever the real-world effect on Russia’s interests, it felt like a provocation to the Kremlin. “NATO enlargement didn't actually harm Russia. It didn't pose a security risk,” says James P. Rubin, a former spokesman in Bill Clinton’s State Department. “It only made Russian elites feel bad, and made them feel that their great power status was somehow weakened.”

Among those elites was Putin, for whom NATO’s expansion fit with the 1990s-humiliation narrative. In a recent interview with the filmmaker Oliver Stone, Putin acknowledged that Russia reacts to the alliance’s expansion “emotionally,” adding that Russia is “forced to take countermeasures” against it. “That is, to aim our missile systems at those facilities which we think pose a threat to us,” Putin explained.

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For Putin, the last way Hillary Clinton stoked resentments about the end of the Cold War might have been the most important. Clinton’s “reset” policy briefly improved relations between Washington and Moscow. But Putin was still resentful about Bush-era U.S. political influence in Ukraine, Georgia, and other former Soviet republics. Putin saw steadily rising American funding for civil society and democracy programs in Europe, Central Asia and Russia itself as a form of subversion.

Demonstrators take part in a mass anti-Putin rally on December, 24, 2011 in Moscow, Russia. | Getty

As secretary of state, Clinton liked to talk about those kinds of “soft power” programs as a way to bolster American influence. The Kremlin also saw her as a fellow traveler of neoconservatives, who believe that America’s has a global calling to push a foreign policy guided by democracy and human rights promotion.

But it wasn’t until December 2011 that Putin came to see Hillary Clinton as a direct threat to his power. That was when unusually large protests appeared in the frigid streets of Moscow. Though sparked by allegedly rigged parliamentary elections, the demonstrations morphed into something more, with shouts of “Putin is a thief!” and “Russia without Putin.” Putin had seen nothing like it since first coming to power more than a decade earlier. For an autocrat and former spy who U.S. officials call both paranoid and rightfully conscious that a sudden loss of power could land him in jail or worse, it was a dire threat.

And in Putin’s view, Clinton piled on. She offered supportive words about the protests, expressing “concerns” about the parliamentary elections and saying the U.S. “supports the rights and aspirations of the Russian people.” To Western ears, it was boilerplate pro-democracy talk, not exactly a call to arms against the government in Moscow. But Putin treated it that way. He fumed that Clinton had “sent a signal” to the protesters and accused the U.S. of backing election observers who, he said, had a subversive agenda. “We need to safeguard ourselves from this interference in our internal affairs and defend our sovereignty,” Putin said.

Some U.S. officials believed that Putin—like so many autocrats who finger foreigner provocateurs for domestic unrest—had found a handy political villain in Clinton. But Clinton herself came to believe he was out for vengeance, as she told donors at a closed-door event on December 15. And other Russia experts believe Putin was genuinely infuriated.

“He was incensed,” said Dmitri Trenin, director of the Moscow Center at the Carnegie Endowment for International Peace. “The State Department became more sinister in the eyes of the Russian media than the CIA was during the Cold War.”



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Putin won that election, and his return to the presidency in 2012—along with a political crackdown that began around the same time—troubled U.S. officials. But the Obama administration was slow to detect Putin’s new assertiveness. After Mitt Romney warned during the 2012 presidential campaign that Russia was America’s “top geopolitical foe,” Barack Obama quipped in one debate with Romney that “[t]he 1980s are now calling to ask for their foreign policy back, because the Cold War’s been over for 20 years.”

But Romney was onto something. Putin hadn't given up his fight. He shifted his attention from domestic political intrigue to exercising Russian power abroad—and restoring Russia to what he considers its rightful place on the global stage.

After another pro-Western uprising in Ukraine, Putin seized the country’s Crimean peninsula. He supported a pro-Russian separatist movement in eastern Ukraine, where combat has left nearly 10,000 people dead. And his unexpected military intervention in Syria, Moscow’s longtime chief ally in the Middle East, boxed in Obama; it has recently left him looking impotent as Russian forces join up with Syrian’s regime in a vicious campaign to drive rebel forces from Aleppo.

In a March 2014 address shortly after claiming Crimea, Putin made clear that he was re-establishing Russia’s place in the global order. He said the world had to “accept the obvious fact: Russia is an independent, active participant in international affairs. Like other countries, it has its own national interests that need to be taken into account and respected.” Translation: Russia would no longer be seated at the kids’ table while Washington dictated world events.

Increasingly, it has become clear that another foreign nation where Russia has exercised its new influence is the United States itself, where Hillary Clinton’s campaign was beset for months by a steady flow of stolen emails—hacked, according to U.S. intelligence officials, by agents of the Kremlin, likely at Putin’s personal direction.

It’s impossible to measure the precise effect of the leaked emails on Clinton’s candidacy. But her defeat was unquestionably a win for Putin, who will soon greet an American president leading what could be the most Russia-friendly administration in U.S. history. Putin sent Donald Trump his congratulations within an hour of Clinton’s concession. And when word of Trump’s election reached the Russian Duma, spontaneous applause broke out in the room.

And why not? Trump has questioned NATO’s value and relevance, and raised doubts about whether he will guarantee the defense of its most vulnerable members, including the Baltic states—positions no American president has ever so much as entertained. He has suggested he would consider removing sanctions imposed over Ukraine and perhaps even recognize Crimea as part of Russia, despite bipartisan revulsion at the idea in Congress.

U.S, Secretary of State Hillary Clinton meets with Russian Prime Minister Vladimir Putin outside Moscow in Novo-Ogarevo on March 19, 2010. | Getty

This is not the future Bill Clinton had hoped for two decades ago. He foresaw a rejuvenated Russia—but one that would be integrated into Europe, with a blossoming democracy, a free market, and a contributor to stability and security there. Instead the opposite has happened: Russia has become a repressive security state that is working to undermine Western democracy while it rattles a nuclear saber at NATO.

For all his bare-chested-on-horseback posturing, Putin’s Russia is still beset by problems. Its economy remains stunted, hobbled in part by U.S. and European sanctions over Ukraine. Russia experts and U.S. officials say Moscow remains deeply insecure over its place in the world. But there is also a new optimism in the Kremlin, they say—particularly now that America, perhaps with Russian assistance, has elected Trump.

“I think Russia has bounced back since the end of the Cold War,” said Trenin. “Russia is a rare major power that has bounced back after a historical defeat." Trenin wouldn’t go so far as to say that the country that lost the Cold War has now managed to win the aftermath. But, he said: “Russia is getting back on its feet as a major power.”

Whatever else Trump augurs for the world, it’s clear what he means for Russia: His surprise victory ended the Clintons’ long run at the center of American power, and his avowed respect for the autocratic Putin marks a decisive recovery from the embarrassment and second-tier status that has needled the Kremlin leader for two decades.

It’s hard to imagine anyone could have foreseen this reversal 15 years ago, but there were inklings. During Bill Clinton’s last visit with Yeltsin, at the Russian’s dacha outside Moscow in June 2000, Clinton shared his concerns about Putin, the former KGB man emerging from the shadows. He already seemed to realize something might be slipping away.

“You’ve got the fire in your belly of a real democrat and a real reformer. I’m not sure Putin has that,” Clinton said, according to Talbott. Clinton added that he had been “lucky” to have Yeltsin as a partner.

In the car afterward, Clinton turned to Talbott. “I think we’re going to miss him,” he said.