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In early November, months before the war began, CIA Director William Burns visited Moscow to deliver a warning: The U.S. believed Russian President Vladimir Putin was preparing to invade Ukraine. If he went ahead, he would face crippling sanctions from a united West.

The American spy chief was connected on a secure Kremlin phone with Mr. Putin, who was in the Black Sea resort of Sochi, isolated from all but a few confidants. The Russian leader made no effort to deny Mr. Burns’ charge. Instead, he calmly recited a list of grievances about how the U.S. had for years ignored Russian security concerns.

As for Ukraine, Mr. Putin told Mr. Burns, it wasn’t a real country.

After returning to Washington, the CIA chief advised President Biden that Mr. Putin hadn’t yet made an irrevocable decision, but was strongly disposed to invade. With European nations heavily dependent on Russian energy, the Russian military modernized, Germany going through a change of governments and the U.S. increasingly focused on a rising China, Mr. Putin gave every sign of seeing this winter as his best opportunity to bring Ukraine back under Moscow’s control.

Over the next three months, Washington struggled to persuade its European allies to mount a unified front. The U.S. itself was trying to balance two aims: talking Mr. Putin down while avoiding actions that he might treat as a provocation; and arming Ukraine to make an invasion as costly as possible.

In the end, the West managed neither to deter Mr. Putin from invading Ukraine nor reassure him that Ukraine’s increasing westward orientation didn’t threaten the Kremlin.

By now, this had become a well-established pattern. For nearly two decades, the U.S. and the European Union vacillated over how to deal with the Russian leader as he resorted to increasingly aggressive steps to reassert Moscow’s dominion over Ukraine and other former Soviet republics.

A look back at the history of the Russian-Western tensions, based on interviews with more than 30 past and present policy makers in the U.S., EU, Ukraine and Russia, shows how Western security policies angered Moscow without deterring it. It also shows how Mr. Putin consistently viewed Ukraine as existential for his project of restoring Russian greatness. The biggest question thrown up by this history is why the West failed to see the danger earlier.

Washington, under both Democratic and Republican presidents, and its allies at first hoped to integrate Mr. Putin into the post-Cold War order. When Mr. Putin balked, the U.S. and its European partners had little appetite for returning to the strategy of containment the West imposed against the Soviet Union. Germany, Europe’s biggest economy, led the EU’s big bet on peace through commerce, developing a dependence on Russian oil and gas that Berlin is now under international pressure to reverse.

The North Atlantic Treaty Organization made a statement in 2008 that Ukraine and Georgia would one day join, and over nearly 14 years never followed through on membership. The EU drew up a trade deal with Ukraine without factoring in Russia’s strong-arm response. Western policies didn’t change decisively in reaction to limited Russian invasions of Georgia and Ukraine, encouraging Mr. Putin to believe that a full-blown campaign to conquer Ukraine wouldn’t meet with determined resistance—either internationally or in Ukraine, a country whose independence he said repeatedly was a regrettable accident of history.

***

Vladimir Putin celebrates the fourth anniversary of Russia's annexation of Crimea in Moscow in 2018.

PHOTO: MLADEN ANTONOV/AGENCE FRANCE-PRESSE/GETTY IMAGES

The roots of the war lie in Russia’s deep ambivalence about its place in the world after the end of the Soviet Union. A diminished Russia needed cooperation with the West to modernize its economy, but it never reconciled itself to the loss of control over neighbors in Europe’s east.

No neighbor was as important to Russia’s sense of its own destiny as Ukraine. The czars’ takeover of the territories of today’s Ukraine in the 17th and 18th centuries was crucial to Russia’s emergence as a major European empire. Collapsing Russian empires lost Ukraine to independence movements amid defeat in World War I and again in 1991, when Ukrainians voted overwhelmingly for independence.

After the chaotic 1990s, the security-service veterans around Mr. Putin who took over Russia’s government complained bitterly about what they saw as the West’s encroachment on Moscow’s traditional sphere of influence in Central and Eastern Europe. An array of newly democratic countries that had been Moscow’s satellites or former Soviet republics joined NATO and the EU, seeing membership of both institutions as the best guarantee of their sovereignty against a revival of Russian imperial ambitions.

Key moments in NATO’s eastward expansion

Since the end of the Cold War, a string of countries have joined NATO or sought to do so.

Existing members

Joined

Aspiring members*

1990s

RUSSIA

Former

East Germany

POLAND

GERMANY

UKRAINE*

CZECH REP.

HUNGARY

2000-2010

RUSSIA

ESTONIA

LATVIA

LITHUANIA

UKRAINE

GEORGIA

SLOVAKIA

ROMANIA

SLOVENIA

CROATIA

BULGARIA

BOS & HERZ.

ALBANIA

2017 and 2020

RUSSIA

UKRAINE

N. MACEDONIA

(2020)

MONTENEGRO (2017)

* In 2008, NATO said Ukraine and Georgia would be members one day. NATO gave Bosnia a Membership Action Plan in 2010. The U.S. and Canada (not pictured) were founding members of NATO in 1949. Current international borders shown except where noted.

Source: NATO
Jemal R. Brinson/THE WALL STREET JOURNAL

Viewed from elsewhere in Europe, NATO’s eastward enlargement didn’t threaten Russia’s security. NATO membership is at core a promise to collectively defend a member that comes under attack. The alliance agreed in 1997 not to permanently station substantial combat forces in its new eastern members that were capable of threatening Russian territory. Russia retained a massive nuclear arsenal and the biggest conventional forces in Europe.

Mr. Putin thought of Russian security interests more broadly, linking the preservation of Moscow’s influence in adjacent countries with his goals of reviving Russia’s global power and cementing his authoritarian rule at home.

The link became clear in Ukraine’s 2004 presidential election. Mr. Putin let the U.S. know in advance who should win.

When White House national security adviser Condoleezza Rice visited Mr. Putin at his dacha outside Moscow in May that year, the Russian leader introduced her to Ukrainian presidential contender Viktor Yanukovych. Ms. Rice concluded that Mr. Putin had arranged the surprise encounter to signal his close interest in the election’s outcome, she recalled in a recent interview.

Mr. Yanukovych’s initial election victory was marred by allegations of fraud and voter intimidation, triggering weeks of street protests and strikes that were dubbed the Orange Revolution. Ukraine’s supreme court ordered a new vote, which pro-Western candidate Viktor Yushchenko won.

The Kremlin saw the Orange Revolution as U.S.-sponsored destabilization aimed at pulling Ukraine out of Moscow’s orbit—and as a prelude to a similar campaign in Russia itself.

A Ukrainian supporter of opposition candidate Viktor Yushchenko cries as he listens to him deliver a speech at a mass rally in Kyiv in 2004.

PHOTO: DAVID GUTTENFELDER/ASSOCIATED PRESS

Mr. Yushchenko was swept into power during the Orange Revolution, seen as a threat by Mr. Putin.

PHOTO: ALEXANDER ZEMLIANICHENKO/ASSOCIATED PRESS

To ease Moscow’s concerns, the Bush administration outlined the limited financial support it had given to Ukrainian media and nongovernmental organizations in the name of promoting democratic values. It totaled $14 million. The White House thought the modest sum was consistent with Mr. Bush’s “freedom agenda” of supporting democracy but hardly enough to change the course of history.

The gesture only confirmed Russian suspicions. “They were impressed at the result that they thought we got for $14 million,” recalled Tom Graham, the senior director for Russia on Mr. Bush’s National Security Council.

Three months after losing Ukraine’s government to a pro-Western president, Mr. Putin decried the breakup of the Soviet Union as “the greatest geopolitical catastrophe of the century.”

U.S. intelligence learned in 2005 that Mr. Putin’s government had carried out a broad review of Russian policy in the “near abroad,” as the Kremlin termed former Soviet republics. From now on, Russia would take a more assertive approach and vigorously contest perceived U.S. influence.

Ukrainian officials heard the message too. When President Yushchenko’s chief of staff, Oleh Rybachuk, visited the Kremlin in November 2005, he discussed the Orange Revolution with Mr. Putin. Mr. Rybachuk described the street protests as an indigenous movement of Ukrainians who wanted to choose their own political course.

Mr. Putin brusquely dismissed the notion as nonsense. He said he had read all of his intelligence services’ reports and knew the movement had been orchestrated by the U.S., the EU and George Soros, Mr. Rybachuck recalled in an interview.

At a separate encounter, Mr. Bush asked Mr. Putin why he thought the end of the Soviet Union had been the greatest tragedy of the 20th century. Surely the deaths of more than 20 million Soviet citizens in World War II was worse, Mr. Bush said. Mr. Putin replied that the USSR’s demise was worse because it had left 25 million Russians outside the Russian Federation, according to Ms. Rice, who was present.

Mr. Putin showed another face to Western European interlocutors, however, encouraging them to believe that he wanted Russia to be part of the wider European family. Soon after becoming president, he wowed Germany’s Parliament with a speech promising to build a strong Russian democracy and work with the West. Speaking in fluent German, perfected while he was a KGB officer in the former East Germany, he declared: “The Cold War is over.”

George W. Bush, right, and Vladimir Putin walk to a press conference at the Bush family compound in Kennebunkport, Maine, in July of 2007.

PHOTO: SAUL LOEB/AGENCE FRANCE-PRESSE/GETTY IMAGES

He charmed politicians and business leaders around Europe and opened pathways for lucrative trade. European leaders called Russia a “strategic partner.” German Chancellor Gerhard Schröder and Italian Premier Silvio Berlusconi were among those who considered him a close friend.

Mr. Putin was personally active in facilitating good economic relations, recalled longtime German diplomat Wolfgang Ischinger. In one meeting, the issue of bureaucratic obstacles to German purchases of Russian wood came up. Mr. Putin phoned the relevant minister and resolved the matter in minutes.

“Putin said ‘Right, problem solved—what’s next?’ ” Mr. Ischinger remembered.

Perceptions changed in January 2007, when Mr. Putin vented his growing frustrations about the West at the annual Munich Security Conference. In a long and icy speech, he denounced the U.S. for trying to rule a unipolar world by force, accused NATO of breaking promises by expanding into Europe’s east, and called the West hypocritical for lecturing Russia about democracy. A chill descended on the audience of Western diplomats and politicians at the luxury Hotel Bayerischer Hof, participants recalled.

“We didn’t take the speech as seriously as we should have,” said Mr. Ischinger. “It takes two to tango, and Mr. Putin didn’t want to tango any more.”

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Mr. Putin’s demeanor with pro-Western leaders became more aggressive. In a meeting with a Balkan head of state during an energy summit in Croatia, Mr. Putin railed against NATO and called its severing of Kosovo from Serbia the greatest violation of international law in recent history. Years later, he would cite Kosovo as a precedent for seizing Crimea from Ukraine.

His rage rising, Mr. Putin rattled through grievances. He shouted expletives at his translator, who was struggling to keep up.

“The room fell silent. It was incredibly awkward: The president of the mighty Russian Federation was bullying a mere interpreter trying to do their job,” one participant said.

Russian President Vladimir Putin delivered a scathing speech at the 2007 Munich Security Conference.

PHOTO: OLIVER LANG//DDP/AGENCE FRANCE-PRESSE/GETTY IMAGES

Ukrainian President Viktor Yushchenko, German Chancellor Angela Merkel, U.S. Secretary of Defense Robert Gates, and U.S. Senators John McCain and Joe Lieberman attend the 2007 Munich conference.

PHOTO: JOERG KOCH/DDP/AGENCE FRANCE-PRESSE/GETTY IMAGES

In Ukraine, President Yushchenko was struggling to fulfill the hopes of the Orange Revolution that the country could become a prosperous Western-style democracy. Fractious politics, endemic corruption and economic stagnation sapped his popularity.

Mr. Yushchenko sought to anchor Ukraine’s place in the West. At the World Economic Forum in Davos in January 2008, he met with Ms. Rice, by then the U.S. Secretary of State, and implored her for a path to enter NATO. The procedure for joining the alliance was called a Membership Action Plan, or MAP.

“I need a MAP. We need to give the Ukrainian people a strategic focus on the way ahead. We really need this,” Mr. Yushchenko said, Ms. Rice recalled.

Ms. Rice, who was initially uncertain about having Ukraine in NATO, gave a noncommittal answer. When the request was debated in the National Security Council, Mr. Bush said NATO should be open to all countries that qualify and want to join.

A NATO summit was set for April 2008 in Bucharest, in the vast Palace of the Parliament built for Romania’s former Communist dictator Nicolae Ceauşescu. The alliance’s summits are usually well scripted in advance. Try as it might, the White House couldn’t overcome German and French resistance to offering a MAP to Ukraine and Georgia.

Berlin and Paris pointed to unsolved territorial conflicts in Georgia, low public support for NATO in Ukraine, and the weakness of democracy and the rule of law in both.

Ms. Merkel, remembering Mr. Putin’s speech in Munich, believed he would see NATO invitations as a direct and deliberate threat to him, according to Christoph Heusgen, her chief diplomatic adviser at the time. She was also convinced Ukraine and Georgia would bring NATO no benefits as members, Mr. Heusgen said.

Ms. Merkel told Mr. Putin in advance that NATO wouldn’t invite Ukraine and Georgia to join, because the alliance was split on the issue, but the Russian leader remained nervous, Mr. Heusgen recalled.

As the NATO summit approached, Mr. Bush held a videoconference with Ms. Merkel, but it soon became clear that no consensus would be reached beforehand.

“Looks like a shootout at the OK Corral,” Mr. Bush said, according to James Jeffrey, the president’s deputy national security adviser at the time.

Ms. Merkel was flummoxed by the American reference and turned to her interpreter, who confessed that he, too, had no idea what the U.S. president meant.

Over dinner in Bucharest, Mr. Bush made his case for giving Ukraine and Georgia a MAP—to no avail. The next day, Ms. Rice and national security adviser Stephen Hadley tried to find a compromise with their German and French counterparts.

Ms. Rice, a Soviet and Russia expert, said Mr. Putin wanted to use Ukraine, Belarus and Georgia to rebuild Russia’s global power, and that extending the shield of NATO membership could be the last chance to stop him. German and French officials were skeptical, believing Russia’s economy was too weak and dependent on Western technology to become a serious threat again.

A woman surveys bomb damage in Gori, Georgia, after Russia invaded in 2008.

PHOTO: URIEL SINAI/GETTY IMAGES

In the final session, Ms. Merkel debated in a corner of the room with leaders from Poland and other eastern members of NATO, who advocated strenuously on behalf of Ukraine and Georgia. Lithuanian President Valdas Adamkus strongly criticized Ms. Merkel’s stance, warning that a failure to stop Russia’s resurgence would eventually threaten the eastern flank of the alliance.

Mr. Bush asked Ms. Rice to go join the animated discussion. The only common language among Ms. Merkel, the east European leaders and Ms. Rice was Russian. So a compromise statement was negotiated in Russian and then drafted in English, Ms. Rice said.

“We agreed today that these countries will become members of NATO,” it read. But it didn’t say when. And there was no MAP.

Many of Ukraine’s supporters were heartened. But some officials in Bucharest feared it was the worst of both worlds. NATO had just painted a target on the backs of Ukraine and Georgia without giving them any protection.

“The fact is we rejected Ukraine’s application and, yes, we left Ukraine in a gray zone,” Radoslaw Sikorski, Poland’s foreign minister at the time, said in an interview.

Mr. Putin joined the summit the next day. He spoke behind closed doors and made clear his disdain for NATO’s move, describing Ukraine as a “made-up” country.

In public comments that day, he also questioned whether Crimea had been properly transferred from Russia to Ukraine during the Soviet era. Daniel Fried, who was the top State Department official on Europe, and Mariusz Handzlik, then the national security adviser to Poland’s president, jumped to their feet in shock. It was an early sign that Mr. Putin wouldn’t let the status quo stand.

Four months later, the Russian army invaded Georgia, exploiting a conflict between Georgia’s government and Russian-backed separatists. Russia didn’t take Tbilisi, the Georgian capital, but it showed it had no qualms about intervening in neighboring countries that wanted to join NATO.

Mr. Putin’s fears of a Ukrainian-style popular revolution infecting Russia were heightened by a wave of demonstrations in Russian cities beginning in 2011, when tens of thousands took to the streets to protest against the lack of democracy. “For fair elections” was the protesters’ slogan.

Mr. Putin believed the protests were a U.S.-sponsored effort to overthrow him, said Ivan Krastev, a Bulgarian political scientist who later attended a dinner hosted by Mr. Putin in Sochi. The Russian president told his guests that people didn’t take to the streets spontaneously but rather were incited by the U.S. Embassy, Mr. Krastev said. “He really believes it.”

The Kremlin organized large countermarches, which were billed as “anti-Orange demonstrations.”

Sporadic pro-democracy protests continued for nearly two years, despite rising repression. Mr. Putin cracked down on opposition parties, free media and nongovernmental organizations.

The concurrent Arab Spring protests, which toppled several authoritarian rulers in the Middle East, further heightened Mr. Putin’s fear, said Mr. Heusgen, the adviser to Ms. Merkel.

“He then became a fervent nationalist,” said Mr. Heusgen. “His great anxiety was that Ukraine could become economically and politically successful and that the Russians would eventually ask themselves ‘Why are our brothers doing so well, while our situation remains dire?’ ”

Ukraine hung in the balance again.

President Putin believed the U.S. was behind pro-democracy rallies in Russia, such as the 'march of millions' protesting his inauguration in 2012.

PHOTO: SERGEI ILNITSKY/EPA/SHUTTERSTOCK

Thousands celebrate Mr. Putin's presidential election victory in Moscow on March 4, 2012.

PHOTO: JOHN MACDOUGALL/AGENCE FRANCE-PRESSE/GETTY IMAGES

Mr. Yushchenko slumped to 5% of the vote in Ukraine’s 2010 presidential elections. Mr. Yanukovych won—fairly this time, said international observers—after campaigning for friendly relations with the West and also Russia. He found it was difficult to have both.

Mr. Yanukovych negotiated a free-trade agreement with the EU. At the same time, however, he was under pressure from Mr. Putin to join a customs union with Russia, Belarus and Kazakhstan. EU officials said Kyiv couldn’t do both, because the customs rules would clash.

The EU, following its standard playbook on trade and governance, demanded that Ukraine revamp its judiciary and improve the rule of law as a precondition for a trade deal. Russia used sticks and carrots: At various moments it blocked goods imports from Ukraine, but it also offered Kyiv cheaper gas prices and a $15 billion loan.

In November 2013, Kyiv abruptly suspended talks with the EU, citing Russian pressure. Mr. Putin called the draft EU-Ukraine deal a “major threat” to Russia’s economy.

At an EU summit in Lithuania, Mr. Yanukovych defended the suspension and asked the EU to include Moscow in a three-way negotiation about the deal. EU leaders replied that letting a third party infringe on others’ sovereignty was unacceptable.

“We expected more,” Ms. Merkel sternly told Mr. Yanukovych in a conversation caught on camera.