In September 2001, as the U.S. reeled from the terrorist attacks on the World Trade Center and the Pentagon, Vladimir Putin supported Washington’s imminent invasion of Afghanistan in ways that would have been inconceivable during the Cold War.

He agreed that U.S. planes carrying humanitarian aid could fly through Russian airspace. He said the U.S. military could use air bases in former Soviet republics in Central Asia. And he ordered his generals to brief their U.S. counterparts on their ill-fated 1980s occupation of Afghanistan.

During Putin’s visit to President George W. Bush’s Texas ranch two months later, Bush, speaking at a high school, declared Putin “a new style of leader, a reformer, a man who’s going to make a huge difference in making the world more peaceful by working closely with the United States.”

It seemed the distrust and antipathy of the Cold War were fading.

Then, just weeks later, Bush announced that Washington was withdrawing from the Anti-Ballistic Missile treaty so it could build a system in Eastern Europe to protect NATO allies and U.S. bases from an Iranian missile attack.

In a nationally televised address, Putin warned that the move would undermine arms control and nonproliferation efforts. “This step has not come as a surprise to us,” Putin said. “But we believe this decision to be mistaken.”

The sequence of events early in Washington’s relationship with Putin reflects a dynamic that has persisted through the ensuing 14 years and the current crisis in Ukraine: U.S. actions — some intentional and some not — sparking an overreaction from an aggrieved Putin.

As Moscow masses tens of thousands of troops along the Russian-Ukrainian border, Putin is thwarting what the Kremlin says is an American plot to surround Russia with hostile neighbors. Experts said he is also promoting “Putinism” — a conservative, ultranationalist form of state capitalism — as a global alternative to Western democracy.

Some current and former U.S. officials say the new dynamic reflects an American failure to recognize that while the Soviet Union is gone as an ideological enemy, Russia has remained a major power that demands the same level of foreign policy attention as China and other large nations — a relationship that should not just be a means to other ends, but an end in itself.

“I just don’t think we were really paying attention,” said James F. Collins, who served as the U.S. ambassador to Moscow in the late 1990s. The bilateral relationship “was seen as not a big deal.”

Putin was never going to be an easy partner. He is a Russian nationalist with authoritarian tendencies who, like his Russian predecessors for centuries, harbors a deep distrust of the West, according to senior U.S. officials. Much of his world view was formed as a KGB officer in the twilight years of the Cold War and as a government official in the chaotic post-Soviet Russia of the 1990s, which Putin and many other Russians view as a period when America repeatedly took advantage of Russian weakness.Since becoming Russia’s president in 2000, Putin has made restoring Russia’s strength — and its traditional sphere of influence — his central goal. He has also cemented his hold on power, systematically quashed dissent and used Russia’s energy supplies as a billy club against its neighbors. Aided by high oil prices and Russia’s United Nations Security Council veto, Putin has perfected the art of needling American presidents, at times obstructing U.S. policies.

Officials from the administrations of Presidents Bush and Barack Obama said American officials initially overestimated their potential areas of cooperation with Putin. Then, through a combination of overconfidence, inattention and occasional clumsiness, Washington worsened a deep spiral in relations with Moscow.

Common cause

Bush and Putin’s post-2001 camaraderie foundered on a core dispute: Russia’s relationship with its neighbors. In November 2002, Bush backed NATO’s invitation to seven nations — including former Soviet republics Estonia, Latvia and Lithuania — to begin talks to join the Western alliance. In 2004, with Bush as a driving force, the seven joined NATO.

Putin and other Russian officials asked why NATO continued to grow when the enemy it was created to fight, the Soviet Union, had ceased to exist. And they asked how NATO expansion would counter new dangers such as terrorism and proliferation.

Thomas E. Graham, who served as Bush’s senior director for Russia on the National Security Council, said a larger effort should have been made to create a new post-Soviet, European security structure that replaced NATO and included Russia.

Graham said small, incremental attempts to test Russian intentions in the early 2000s in Afghanistan, for example, would have been low-risk ways to gauge Putin’s sincerity. “Our policy never tested Putin to see whether he was really committed to a different type of relationship.”

But Vice President Dick Cheney, Sen. John McCain and other conservatives, as well as hawkish Democrats, argued that Moscow should not be given veto power over which nations could join the alliance and that no American president should rebuff demands from Eastern Europeans to escape Russian dominance.

Another core dispute between Bush and Putin was related to democracy. What Bush and other American officials saw as democracy spreading across the former Soviet bloc, Putin saw as pro-American regime change.

The 2003 U.S.-led invasion of Iraq, without U.N. authorization and over the objections of France, Germany and Russia, was a turning point for Putin. He said the war made a mockery of American claims of promoting democracy abroad and upholding international law.

Putin was also deeply skeptical of U.S. efforts to nurture democracy in the former Soviet bloc, where the State Department and American nonprofit groups provided training and funds to local civil society groups. He accused the United States of meddling.

In late 2003, protests in the former Soviet republic of Georgia led to the election of a pro-Western leader. Four months later, street protests in Ukraine resulted in a pro-Western president taking office.

Putin saw both developments as American-backed plots and slaps in the face, according to senior U.S. officials.

Three train wrecks

Bush’s relationship with Putin unraveled in 2008. In February, Kosovo declared independence from Serbia with the support of the United States — a step that Russia, a longtime supporter of Serbia, had been trying to block diplomatically for more than a decade. In April, Bush won support at a NATO summit for the construction of a missile defense system in Eastern Europe.

Bush called on NATO to give Ukraine and Georgia a formal process that would put each on a path toward eventually joining the alliance. France and Germany blocked him and warned that further NATO expansion would spur an aggressive Russian stance when Moscow regained power.

In the end, the alliance simply issued a statement saying the two countries “will become members of NATO.” That risked the worst of both worlds: antagonizing Moscow without giving Kiev and Tbilisi a road map to join NATO.

The senior U.S. official said these steps amounted to “three train wrecks” from Putin’s point of view, exacerbating his sense of victimization. “Doing all three of those things in kind of close proximity — Kosovo independence, missile defense and the NATO expansion decisions — sort of fed his sense of people trying to take advantage of Russia,” he said.

In August 2008, Putin struck back. After Georgia launched an offensive to regain control of the breakaway pro-Russian region of South Ossetia, Putin launched a military operation that expanded Russian control of South Ossetia and a second breakaway area, Abkhazia.

The Bush administration, tied down in Iraq and Afghanistan, publicly protested but declined to intervene militarily in Georgia. Putin emerged as the clear winner and achieved his goal of standing up to the West.

Only one major issue

After his 2008 election victory, Obama carried out a sweeping review of Russia policy. Its primary architect was Michael McFaul, a Stanford University professor and vocal proponent of greater democracy in Russia who took the National Security Council position previously held by Graham.

In a recent interview, McFaul said that when Obama’s new national security team surveyed the administration’s primary foreign policy objectives, they found that few involved Russia. Only one directly related to bilateral relations with Moscow: a new nuclear arms reduction treaty.

The result, McFaul said, was that relations with Moscow were seen as important in terms of achieving other goals, and not as important in terms of Russia itself.

Obama’s new Russia strategy was called “the reset.” In July 2009, he traveled to Moscow to start implementing it.

In an interview with the Associated Press a few days before leaving Washington, Obama chided Putin, who had become prime minister in 2008 after reaching his two-term constitutional limit as president. Obama said the United States was developing a “very good relationship” with the man Putin had anointed as his successor, Dmitry Medvedev, and accused Putin of using “Cold War approaches” to relations with Washington.

In Moscow, Obama spent five hours meeting with Medvedev and only one hour meeting with Putin, who was still widely seen as the country’s real power.

After their meeting, Putin said U.S.-Russian relations had gone through various stages. “There were periods when our relations flourished quite a bit and there were also periods of, shall we say, grayish mood between our two countries and of stagnation,” he said as Obama sat a few feet away.

At first, the reset fared well. During Obama’s visit, Moscow agreed to greatly expand Washington’s ability to ship military supplies to Afghanistan via Russia. In April 2010, the United States and Russia signed the New START treaty, further reducing the U.S. and Russian nuclear arsenals. Later that year, Russia supported sweeping new U.N. economic sanctions on Iran and blocked the sale of sophisticated Russian-made S-300 anti-aircraft missile systems to Tehran.

Experts said the two-year honeymoon was the result of the Obama administration’s engaging Russia on issues where the two countries shared interests, such as reducing nuclear arms, countering terrorism and nonproliferation. The same core issues that sparked tensions during the Bush administration — democracy and Russia’s neighbors — largely went unaddressed.

A vaporized relationship

In 2012, Putin was elected to a third term as president and launched a sweeping crackdown on dissent and re-centralization of power. McFaul, then the U.S. ambassador in Moscow, publicly criticized the moves.

In the recent interview, McFaul blamed Putin for the collapse in relations. He said Putin rebuffed repeated invitations to visit Washington when he was prime minister and declined to attend a G-8 meeting in Washington after he again became president. Echoing Bush-era officials, McFaul said it is politically impossible for a U.S. president to trade Russian cooperation on Iran, for example, for U.S. silence on democracy in Russia and Moscow’s pressuring of its neighbors.

In 2013, U.S.-Russian relations plummeted. In June, Putin granted asylum to National Security Agency whistle-blower Edward Snowden. Obama, in turn, canceled a planned summit meeting with Putin in Moscow that fall. It was the first time a U.S. summit with the Kremlin had been canceled in 50 years.

Last fall, demonstrators in Kiev began demanding that Ukraine move closer to the EU. At the time, the White House was deeply skeptical of Putin and paying little attention to the former Soviet bloc.

Deferring to Europeans, the Obama administration backed a plan that would have moved Ukraine closer to the EU and away from a pro-Russian economic bloc created by Putin. Critics said it was a mistake to make Ukraine choose sides.

Jack F. Matlock, who served as U.S. ambassador to Moscow from 1987 to 1991, said that years of escalating protests by Putin made it clear he believed the West was surrounding him with hostile neighbors. And for centuries, Russian leaders have viewed a friendly Ukraine as vital to Moscow’s defense.

“The real ‘red line’ has always been Ukraine,” Matlock said. “When you begin to poke them in the most sensitive area . . . you are going to get a reaction that makes them a lot less cooperative.”

American experts said it is vital for the U.S. to establish a new long-term strategy toward Russia that does not blame the current crisis solely on Putin.

Matthew Rojansky, a Russia expert at the Wilson Center, argued that demonizing Putin reflected the continued failure of American officials to recognize Russia’s power, interest and importance.

“Putin is a reflection of Russia,” Rojansky said. “This weird notion that Putin will go away and there will suddenly be a pliant Russia is false.”

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