The old Caucasus spa town of Kislovodsk was in terminal decline, much like the Soviet Union itself. It was late April 1991, and Secretary of State James Baker and those of us in his bone-tired delegation had just arrived from Damascus. We stumbled around in the evening gloom to find our rooms in the official guesthouse, long past its glory days as a haven for the Communist Party elite. My room was lit by a single overhead bulb. The handle on the toilet came off when I tried to flush it, and what trickled out of the faucet had the same sulfurous smell and reddish tint as the mineral waters for which the town was famous.

I walked down to Baker’s suite to deliver a briefing memo for his meeting the next day with the Soviet foreign minister. The suite was bigger and better lit, with similarly understated decor. Baker smiled wearily and glanced at the paper I handed him. It was covered with notes on all the issues before us: Germany’s peaceful reunification in the fall of 1990, the military triumph over Saddam Hussein little more than a month earlier, the increasingly precarious future of the Soviet Union.

Looking up from the memo, Baker asked: “Have you ever seen anything like this?” I assured him that I hadn’t, and started to tell him about my handleless toilet. “That’s not what I meant,” he said, unable to restrain his laughter. “I’m talking about the world. Have you ever seen so many things changing so damn fast?” Embarrassed, I acknowledged that I hadn’t. “This sure is quite a time,” he said. “I bet you won’t see anything like it for as long as you stay in the Foreign Service.”

He was right. Before the year was out, the Soviet Union had ceased to exist. After a last telephone call as the leader of the U.S.S.R. with President George H. W. Bush, Mikhail Gorbachev resigned on December 25, and his country was no more. Just weeks later, in January 1992, I went with Baker to Moscow. We met with Boris Yeltsin in the Kremlin, where the Russian tricolor flag was flying. It was surreal.

American power and diplomacy were at their peak then. Russian hopes jostled with uncertainty and lingering humiliation. This was the prologue to the tangled and repetitive story of post–Cold War relations between the two countries, in which troubles were never exactly foreordained, but recurred with depressing regularity. And it was, in that sense, where the story of Russian interference in the 2016 U.S. presidential election began. I played a variety of roles in this turbulent relationship, at the American embassy in Moscow and in senior jobs in Washington. Here’s what I saw.

Illustration by Lincoln Agnew; photos by David Brauchli / Peter Turnley / Getty / Alexander Zemlianichenko / AP

I arrived back in Moscow as the U.S. embassy’s chief political officer in 1994, some two and a half years after the Soviet Union’s collapse. The sense of possibility was already fading by then, and the difficulties of constructing something new to replace the old Soviet system were becoming apparent. The embassy, a ramshackle mustard-colored building not far from the Moscow River, had been in service since the 1950s. A fire in 1991 had done considerable damage to it; Russian intelligence agents had rushed to the scene, thinly disguised as firefighters. Nearby stood an Orthodox church thought to be so jam-packed with listening and monitoring equipment that it was known as “Our Lady of Immaculate Reception.” Old habits and mutual suspicions die hard.

Waiting to depart on one wintry trip to the North Caucasus, I watched as a technician for Air Dagestan de-iced the wings of the battered aircraft with a blowtorch.

Across a busy street on the west side of the embassy compound was the Russian White House, which still bore scars from a failed revolt against Yeltsin nine months earlier. Yeltsin himself was a wounded figure. His heroic democratic aura chipped and tarnished, he was drinking too much and governing erratically. The changeover to a market economy had not erased the country’s profound economic and social problems. Industrial production had fallen by half since 1991. Agricultural output was dropping too. At least 30 percent of the population was living below the poverty line, and inflation had wiped out the meager savings of pensioners. The public-health system had collapsed, and contagious diseases such as tuberculosis and diphtheria were reemerging.

Lawlessness was pervasive. One afternoon in the early fall of 1995, someone fired a rocket-propelled grenade at the embassy building. The round pierced a wall on the sixth floor and detonated in a copy machine, sending metal fragments and glass in all directions. Miraculously, no one was injured. It tells you a lot about Moscow in those days that walking around the city in broad daylight with an RPG was not wildly out of the ordinary.

The problems—and the chaos—of Russian life grew even more stark as you traveled away from the capital. In Vladivostok, then the murky heart of Russia’s “wild east,” I talked with local Mafia bosses, expansive in their description of “business possibilities,” none of which sounded much like the new market models that Western advisers were earnestly promoting in Moscow and St. Petersburg. Waiting to depart on one wintry trip to the North Caucasus, I watched as a technician for Air Dagestan, one of Aeroflot’s countless dodgy post-Soviet spin-offs, de‑iced the wings of the battered old Ilyushin aircraft with a blowtorch. In the cockpit, a rheumy-eyed pilot was putting away a half-empty bottle of vodka.

Nothing captured more vividly the disarray of Yeltsin’s Russia than the brutal ineptitude of the first Chechen war. In the spring of 1995, I drove to Grozny, Chechnya’s capital. The Chechen rebel leader, Dzhokhar Dudayev, had only recently retreated with his forces, into the hills. Roadside stands peddled everything from soft drinks and vodka to weapons and ammunition. Atop Soviet-era armored personnel carriers sat Russian troops wearing bandannas, reflector sunglasses, and sleeveless T‑shirts. Equipped with bandoliers and large knives in their belts, they looked more like gang members than professional soldiers.

I drove past burned-out houses and shops in the little town of Samashki, where these same troops, reportedly drunk and eager for revenge after their losses in the war, had the week before massacred 200 Chechens, mostly women, children, and elderly men. In Grozny itself, 40 square blocks had been leveled by Russian bombing during the war—a campaign that left thousands dead. The city looked like a smaller version of Stalingrad in 1943.

It was a terrible sight. It was also a glimpse of how far Russia had fallen since the Soviet Union’s collapse; here were the ill-fed and ill-trained remnants of the Red Army, once reputed to be capable of reaching the English Channel in 48 hours, now unable to suppress a local rebellion in an isolated republic. And here was Boris Yeltsin, who had so courageously defied the hard-liners in August 1991 and buried the Communist system for good, exposed as an infirm leader unable to restore order. The promise of Russia’s post-Communist transition was not yet extinguished, but it was beginning to flicker.

So was the promise of a U.S.-Russian partnership. In December 1994, on the eve of a visit by Vice President Al Gore to Moscow, I had tried to capture Russia’s domestic predicament in a cable to Washington. “Winter in Russia is not a time for optimists, and in some respects the popular mood here mirrors the descending gloom. Born of a mood of national regret over the loss of superpower status and an equally acute sense that the West is taking advantage of Russia’s weakness,” I wrote, assertive policies abroad had become one of the few themes that united Russians. Yeltsin wished to reaffirm Russia’s great-power status, and its interests in the neighboring post-Soviet republics.

President Bill Clinton tried hard to manage Russia’s post-traumatic stress disorder, but his push for the eastward expansion of NATO reinforced Russian resentments. When I left Moscow after my first tour, in early 1996, I worried about the eventual resurgence of a Russia stewing in its own grievances and insecurities. I just had no idea that this would happen so quickly, or that Vladimir Putin—then an obscure bureaucrat—would emerge as the embodiment of that peculiarly Russian combination of qualities.

From May 2001: Russia is finished

“You Americans need to listen more,” President Putin said as I handed him my credentials as ambassador, before I had gotten a word out of my mouth. “You can’t have everything your way anymore. We can have effective relations, but not just on your terms.” It was 2005, and in the ensuing years I would hear that message again and again, as unsubtle and defiantly charmless as the man himself.

Putin had been president for five years then. He seemed in many ways the anti-Yeltsin—younger, sober, fiercely competent, hardworking and hard-faced. Surfing on high energy prices and the benefits of some smart early economic reforms, as well as the ruthlessly successful prosecution of a second Chechen war, he was determined to show that Russia would no longer be the potted plant of major-power politics.

Early on in his Kremlin tenure, Putin had tested, with President George W. Bush, a form of partnership suited to his view of Russian interests and prerogatives. He imagined a common front in the post-9/11 War on Terror, in return for acceptance of Russia’s special influence in the former Soviet Union, with no encroachment by NATO beyond the Baltics and no interference in Russia’s domestic politics. But this kind of transaction was never in the cards. Putin fundamentally misread American interests and politics. The Bush administration had no desire—and saw no reason—to trade anything for a Russian partnership against al‑Qaeda. It had little inclination to concede much to a declining power.

Before long, the excesses of Putinism began to eat up its successes. Corruption deepened, as Putin sought to lubricate political control and steadily monopolize wealth within his circle. His suspicions of America’s motives also deepened. “Uncomfortable personally with political competition and openness, Putin has never been a democratizer,” I wrote in a cable to Secretary of State Condoleezza Rice, pushing my capacity for understatement to its limits. Democracy promotion was, to him, a Trojan horse, designed to further American geopolitical interests at Russia’s expense and erode the sphere of influence that he viewed as a great-power entitlement. When the Orange Revolution in Ukraine and the Rose Revolution in Georgia ousted pro-Russian leaders, Putin’s neuralgia intensified.

In October 2006, I joined Rice in a conversation with Putin, in front of a roaring fire at a Russian presidential compound on the outskirts of Moscow. He’d kept us waiting for some three hours—a regular ploy he used to unsettle and demean foreign leaders. Rice had passed the time calmly, watching a Russian sports station on TV; she betrayed no annoyance when we were finally granted our audience. The discussion meandered, until she began to make a case against Russia’s escalation of tension with Georgia and its pro-NATO, pro-Western president, Mikheil Saakashvili. Like most of the Russian political elite, Putin expected deference from smaller neighbors, and Saakashvili was passionately undeferential.

Putin’s intimidating aura is often reinforced by his controlled mannerisms, modulated tone, and steady gaze. But he can get quite animated if he wants to drive home a point, his eyes flashing and his voice rising in pitch. Standing before the fire, Putin wagged his index finger and warned, “If Saakashvili starts something, we will finish it.” Rice stood at that point too, looming several inches taller than Putin in her heels. Having to look up at the secretary did not improve his disposition.

“Saakashvili is nothing more than a puppet of the United States,” Putin said sharply. “You need to pull back on the strings before there’s trouble.” The fireplace exchange eventually ratcheted down, but tensions over Georgia and Ukraine never did. Putin kept up the pressure. Concerned about the Russian reaction when the Bush administration launched an end-of-term, legacy-defining campaign to open the door to Ukraine’s and Georgia’s membership in NATO, I warned of train wrecks ahead.

On a dreary February afternoon in 2008, as snow fell steadily outside my office window, I wrote a long personal email to Secretary Rice, emphasizing that Putin would see any move toward NATO membership for Ukraine and Georgia as a serious and deliberate challenge. “Today’s Russia will respond,” I continued. “It will create fertile soil for Russian meddling in Crimea and eastern Ukraine. The prospects of subsequent Russian-Georgian conflict would be high.” Within a few months, Putin had baited Saakashvili into conflict, and Russia had invaded Georgia.

“Outside interference in our elections,” Putin told me in 2007, “will not be tolerated.”

Throughout this period, domestic repression was building. Two weeks before Putin and Rice squared off in front of the fireplace, Anna Politkovskaya, a fearless journalist who had covered the wars in Chechnya and a variety of abuses in Russian society, was gunned down in her Moscow apartment building. Some suspected it was no coincidence that the murder happened on Putin’s birthday.

As a mark of respect, and of what the United States stood for, I went to Politkovskaya’s funeral. I recall the day well—a cold autumn afternoon, dusk settling, snowflakes in the air, long lines of mourners (about 3,000 altogether) shuffling slowly toward the hall where her casket lay. Not a single representative of the Russian government showed up.

The following year, in a blunt private conversation with me, Putin accused the U.S. embassy and American NGOs of funneling money and support to critics of the Kremlin in the lead-up to the national elections. “Outside interference in our elections,” he told me, “will not be tolerated.” With the most even tone I could manage, I said that his accusations were baseless, and that the outcome of Russia’s elections was for Russians alone to decide. Putin listened, offered a tight-lipped smile, and replied, “Don’t think we won’t react to outside interference.”

Illustration by Lincoln Agnew; photos by Ludovic Marin / Getty / Ivan Sekretarev / AP

President Barack Obama first met with Putin in Moscow in July 2009, and I accompanied him. I was now the State Department’s undersecretary for political affairs, having concluded my tour as ambassador in May 2008. Putin had handed off the presidency to Dmitry Medvedev and become prime minister, but he remained the ultimate decision maker.

En route to Putin’s dacha outside the city, I suggested that Obama open the meeting with a question. Why not ask Putin for his candid assessment of what he thought had gone right, and what had gone wrong, in Russian-American relations over the past decade? Putin liked being asked his opinion, and he certainly wasn’t shy. Maybe letting him get some things off his chest would set a good tone. The president nodded.

Obama’s initial question produced an unbroken 55-minute monologue filled with grievances, sharp asides, and acerbic commentary. I sat wondering about the wisdom of my advice and my future in the new administration.

Obama listened patiently, and then delivered his own firm message on the possibilities of a “reset” of the relationship. He was matter-of-fact about the two countries’ differences, and didn’t gloss over the profound problems that Russia’s actions in Georgia had caused. He said it was in neither of our interests to let our disagreements obscure those areas where we could each benefit by working together, and where U.S.-Russian leadership could contribute to international order. We should explore the possibilities of cooperation, he explained, without inflating expectations. Putin was wary, but said he was willing to try.

As we rode back to Moscow after the meeting, Hillary Clinton smiled and affirmed that neither she nor her husband would be spending their summer vacation with Putin near the Arctic Circle.

Some eight months later, I accompanied Hillary Clinton, then the secretary of state, to Putin’s dacha. He was mildly combative at the outset of the meeting, while the Russian press was in the room: gloating about American economic difficulties and expressing his skepticism of Washington’s seriousness about strengthening economic relations with Russia. Slouching a little in his chair, his legs spread wide, he looked every bit the sullen and surly kid in the back of the classroom (an image that Obama once, undiplomatically, used himself in public).

The secretary and I had talked earlier that day about Putin’s love of the outdoors and fascination with big animals, as well as the bare-chested persona he obsessively cultivated. She asked him to talk a little about his highly publicized efforts to save Siberian tigers from extinction. Putin’s demeanor changed visibly, and he described with uncharacteristic excitement some of his recent trips to the Russian far east. He stood up and asked Clinton to come with him to his private office. I trailed them down several hallways, past startled guards and assistants. Arriving at his office, he proceeded to show the secretary, on a large map of Russia covering most of one wall, the areas he had visited on his Siberian-tiger trips, as well as areas in the north where he planned to go that summer to tranquilize and tag polar bears. With genuine enthusiasm, he asked whether former President Clinton might like to come along, or maybe even the secretary herself?

I had never seen Putin so animated. The secretary applauded his commitment to wildlife conservation, and said this might be another area where Russia and America could work together more. She politely deflected the invitation, although she promised to mention it to her husband. As we rode back to Moscow after the meeting, Clinton smiled and affirmed that neither she nor her husband would be spending their summer vacation with Putin near the Arctic Circle.

To see Putin so enthusiastic about Siberian wildlife and so dour about nearly every aspect of the U.S.-Russia relationship underscored the limited potential of our ties. With Medvedev in the Kremlin, Obama struggled to stay connected to Putin, whose suspicions never really eased, and who was still inclined to paint the U.S. as a threat in order to legitimize his repressive bent at home. We managed a string of tangible accomplishments: a new nuclear-arms-reduction treaty; a military transit agreement for Afghanistan; a partnership on the Iranian nuclear issue. But the upheavals of the Arab Spring unnerved Putin; he reportedly watched the grisly video of the demise of the Libyan leader Muammar Qaddafi—caught hiding in a drainage pipe and killed by Western-backed rebels—over and over again. Domestically, as oil prices fell and his rickety, resource-dependent economy slowed, he worried that it would be hard to sustain his old social contract, whereby he exercised full control over politics in return for ensuring rising living standards and a measure of prosperity.

When Putin decided to return to the presidency after Medvedev’s term ended in 2012, he was surprised by large street demonstrations, the product of middle-class resentment of worsening corruption and fraudulent parliamentary elections. In a speech in Europe, Clinton sharply criticized the Russian government. “The Russian people, like people everywhere,” she said, “deserve the right to have their voices heard and their votes counted.” Putin took this personally, and blamed Clinton publicly for sending “a signal” that brought protesters into the streets. Putin has a remarkable capacity for storing up slights and grievances, and assembling them to fit his narrative of the West trying to keep Russia down. Clinton’s criticism would rank high in his litany—and help generate an animus that led directly to his meddling against her candidacy in the 2016 U.S. presidential election.

The arc of the U.S.-Russia relationship was already bending in a familiar direction, just as it had, after moments of hope, during the Bush administration, and Bill Clinton’s administration before that. In 2014, the crisis in Ukraine dragged it to new depths. After the pro-Russian president of Ukraine fled during widespread protests, Putin annexed Crimea and invaded the Donbass, in eastern Ukraine. If he couldn’t have a deferential government in Kiev, he wanted to engineer the next best thing: a dysfunctional Ukraine. For a number of years, Putin had challenged the West in places such as Georgia and Ukraine, where Russia had a meaningful stake and a high appetite for risk. In 2016, a year after I left government, he saw an opportunity for a more direct challenge to the West—an attack on the integrity of its democracies.

Who lost Russia? It’s an old argument, and it misses the point. Russia was never ours to lose. Russians lost trust and confidence in themselves after the Cold War, and only they could remake their state and their economy. In the 1990s, the country was in the midst of three simultaneous historical transformations: the collapse of Communism and the transition to a market economy and democracy; the collapse of the Soviet bloc and the security it had provided to historically insecure Russia; and the collapse of the Soviet Union itself, and with it an empire built over several centuries. None of that could be resolved in a single generation, let alone a few years. And none of it could be fixed by outsiders; greater American involvement would not have been tolerated.

The sense of loss and indignity that came with defeat in the Cold War was unavoidable, no matter how many times we and the Russians had told each other that the outcome had no losers, only winners. From that humiliation, and from the disorder of Yeltsin’s Russia, grew the deep distrust and smoldering aggressiveness of Putin’s.

Illustration by Lincoln Agnew; photos by Mikhail Svetlov / Alex Wong / Getty

The pattern in U.S.-Russian relations has sometimes hinted at historical immutability, as if we were bound to rivalry and unending suspicion. That view might contain a kernel of truth; history matters, and is difficult to escape. But the whole truth is more complicated, and more prosaic. We each had our illusions. America thought that Moscow would eventually get accustomed to being our junior partner, and grudgingly accommodate NATO expansion even up to its border with Ukraine. And Russia always assumed the worst about American motives, and believed that its own corrupt political order and unreformed economy were a sustainable basis for real geopolitical power. We tended to feed each other’s pathologies. Too often, we talked past each other.

Today, of course, the American relationship with Moscow is more bizarre, and more troubled, than at any point since the end of the Cold War. In Helsinki last summer, President Donald Trump stood alongside Putin, absolved him of election interference, and publicly doubted the conclusions of America’s intelligence and law-enforcement services.

Trump’s narcissism, breathtaking disregard for history, and unilateral diplomatic disarmament are a depressing trifecta at a moment when Russia poses threats that were unimaginable a quarter century ago. He seems oblivious to the reality that “getting along” with rivals like Putin is not the aim of diplomacy, which is all about advancing tangible interests.

Managing relations with Russia will be a long game, conducted within a relatively narrow band of possibilities. Navigating such a great-power rivalry requires tactful diplomacy—maneuvering in the gray area between peace and war; demonstrating a grasp of the limits of the possible; building leverage; exploring common ground where we can find it; and pushing back firmly and persistently where we can’t.

The path ahead with Russia will get rockier before it gets easier. We ought to traverse it without illusions, mindful of Russia’s interests and sensibilities, unapologetic about our values, and confident in our own enduring strengths. We should not give in to Putin—or give up on the Russia beyond him.