In one of her last acts as secretary of state in early 2013, Hillary Clinton wrote a confidential memo to the White House on how to handle Vladimir Putin, Russia’s newly installed and increasingly aggressive fourth president. Her bluntly worded advice: Snub him.

“Don’t appear too eager to work together,” Clinton urged President Obama, according to her recollection of the note in her 2014 memoir. “Don’t flatter Putin with high-level attention. Decline his invitation for a presidential summit.”

It was harsh advice coming from the administration’s top diplomat, and Obama would ignore key parts of it. But the memo succinctly captured a personal view about Putin on the part of the future Democratic presidential nominee: a deep skepticism, informed by bitter experience, that would be likely to define U.S.-Russian relations if Clinton is elected. Her lasting conclusion, as she would acknowledge, was that “strength and resolve were the only language Putin would understand.”

Putin has been thrust unexpectedly onto the center stage in the U.S. presidential race, with Republican contender Donald Trump expressing admiration for the Kremlin strongman even as intelligence officials investigate apparent Russian attempts to interfere in the campaign. Clinton, by contrast, has used tough talk about Russia to burnish her credentials as an experienced diplomat who can stand up to the United States’ adversaries.

For Clinton, the rhetoric reflects genuine disappointment and frustration from a tumultuous term as secretary of state during which cooperation between Moscow and Washington briefly soared, only to come crashing to Earth after Putin’s reelection as president in 2012, following a four-year hiatus, according to current and former U.S. officials involved in Russian policymaking at the time. Clinton, who began her tenure by famously offering a “reset” of Russian relations, would end it by publicly blasting Putin’s government on issues including alleged vote-rigging in Russia and Putin’s support for authoritarian Syrian President Bashar al-Assad.

Putin would fire back with repeated attacks against her, often injecting an unusually personal tone into the growing diplomatic rift. The exchanges helped cement an adversarial view of Clinton on the Russian side that may explain, more than any other single factor, the apparent efforts by Russian operatives to influence the election by hacking email accounts of senior Clinton staff members, longtime Kremlin observers say.

“She has policies and a history that the Russians don’t like,” said Michael McFaul, who became the U.S. ambassador to Moscow during Clinton’s final year as secretary of state. “It’s frequently forgotten because there’s so much noise about Trump and Putin. But this history is real, and Putin doesn’t forget these things.”

© Fabrice Coffrini/Agence France-Presse via Getty Images Secretary of State Hillary Clinton and Russian Foreign Minister Sergei Lavrov press a red button marked “reset” in English that Clinton handed to Lavrov during a meeting on March 6, 2009…

The ‘reset’ button

Clinton’s strong views about Putin predated her arrival at Foggy Bottom in 2009 as Obama’s first secretary of state. As a U.S. senator, she condemned Russia’s military incursion in August 2008 in the Georgian republic and suggested that Putin, a former Soviet KGB officer who was then Russia’s prime minister, was a throwback to the country’s hegemonic past.

President George W. Bush had famously vouched for Putin’s character in 2001 by saying that he’d looked into the Russian’s eyes and gotten “a sense of his soul.” But Clinton, during her own first presidential campaign in early 2008, insisted that Bush had seen no such thing.

“He was a KGB agent — by definition he doesn’t have a soul,” Clinton said.

Just over a year later, Obama’s surprise choice as secretary of state was tasked with managing the administration’s “Russian reset” policy, which sought to take advantage of the leadership change in both Washington and Moscow to inaugurate a new era of cooperation. The new White House believed Russia’s new president, Dmitry Medvedev — a St. Petersburg politician 13 younger than Putin and lacking his predecessor’s experience in the Soviet bureaucracy — might be more open to a real partnership.

Former State Department and White House officials who attended early strategy meetings said that Clinton ultimately agreed with the approach. But she remained broadly skeptical that the relationship with Russia would ever extend beyond specific issues where Moscow saw an advantage in cooperation.

“The reset was the president’s idea — it was something he wanted to do,” said Philip Gordon, the assistant secretary of state for European and Eurasian affairs during Clinton’s tenure. “But there was this logic that we were in a terrible place with Russia, and we should give it a shot to see if we could get some concrete things done, in our own interest.”

Another senior U.S. official present during the discussions attributed Clinton’s reluctance to lingering suspicions about Putin. The former KGB operative who served as president in the early 2000s had accepted the prime minister’s job under Medvedev, but many Kremlin watchers believed that Putin was still Russia’s de facto leader, and that Obama’s attempts to woo Medvedev misunderstoodthe real power structure in the Kremlin. These observers watched Putin’s hardening view toward the United States with increasing concern.

“It was right to be skeptical that you could translate that [reset] into a durable, strategic partnership,” said the official, who helped guide Russian diplomacy during Republican and Democratic administrations and who spoke on the condition of anonymity to discuss internal policy debates freely. “Structurally, we still faced a lot of problems dealing with Russia,” including a “fundamental difference in worldview.”

The policy’s official launch was a flub: At a Geneva news conference in March 2009, Clinton presented Russian Foreign Minister Sergei Lavrov with a mounted red button emblazoned with the word “reset” in English, and the Russian word “peregruzka” — a translation error by the U.S. team that left the bewildered Lavrov puzzling over a term meaning “overload.”

© Haraz N. Ghanbari/Associated Press Secretary of State Hillary Clinton meets with Russian Foreign Minister Sergei Lavrov on June 29, 2012, in St. Petersburg.

Years later, Lavrov would dismiss the reset as “the invention of Hillary Clinton and the Obama administration.” He noted pointedly in a Bloomberg News interview that he had a very good relationship with Condoleezza Rice, Clinton’s immediate predecessor as secretary of state.

Despite doubts, the new approach seemed initially to bear fruit.

Within a little more than a year, the two governments had notched historic agreements, including a new treaty on reducing nuclear stockpiles and a pact allowing U.S. military planes to use Russian airspace in delivering supplies to troops in Afghanistan.

Americans and Russians, working in unusual accord, achieved striking progress on some of the thorniest disputes before the United Nations. In 2010, Washington and Moscow cooperated on a package of unprecedented U.N. economic sanctions that ultimately drove Iran to negotiations about limiting its nuclear program. The administration worked with Moscow to overcome U.S. objections to Russia’s long-standing effort to join the World Trade Organization.

In 2011, Russia withheld its veto on the U.S.-led effort to authorize the international military campaign to stop Libyan leader Moammar Gaddafi from slaughtering thousands of his own citizens — an act of diplomatic restraint that many U.S. officials regard as the “reset” era’s high-water mark.

“With the reset, we were never seeking goodwill with Russia; we were seeking a new strategy,” said McFaul, the former U.S. ambassador. “It was most productive in terms of concrete outcomes — not holding hands and singing Kumbaya, but real stuff, including some of our biggest security and economic priorities.”

But beneath a more placid surface, old conflicts continued both at home and abroad, and new ones would emerge.

In Washington, many of the administration’s Russian initiatives were drawing skepticism from Congress. In 2010, Obama had announced that he was discontinuing a Bush-era Eastern European missile defense shield that Russia viewed as a military threat, in favor of a new program designed to combat potential strikes from Iranian short- and medium-range missiles. But many Republicans criticized the change — which had been recommended by Defense Secretary Robert M. Gates, a Bush holdover — as an unwarranted and unwise favor to Russia, granted by a naive young administration.

Russian officials began publicly ruing their tacit support for U.N.-approved military action in Libya, after the intervention expanded from a simple civilian-protection mission to a sustained bombing campaign that led to the overthrow and assassination of Gaddafi. The Kremlin now believed it had been tricked into allowing the U.N. resolution to move forward.

Putin, according to U.S. officials who met with him at the time, concluded that the Americans were most interested in pursuing regime change for governments they disliked, first in Baghdad and Tripoli, and later in Damascus. Eventually he became convinced that it was the Kremlin that the United States most wanted to change. Logically, Clinton, a strong proponent of U.S. military action in Libya and Syria, would be on the side of those seeking new leadership in Moscow, he believed.

Suddenly, the Russians were casting skeptical looks at joint programs that had received strong support in both capitals. One casualty was the Nunn-Lugar Cooperative Threat Reduction Program, which funded the dismantling of Soviet-era nuclear, chemical and biological weapons systems to prevent them from being stolen by terrorists or purchased by rogue states.

The program’s co-founder, Sen. Richard G. Lugar (Ind.), who served as the ranking Republican on the Senate Foreign Relations Committee during Clinton’s tenure, began noticing a change in tone during his many visits to meet with the initiative’s Russian partners. Powerful Russian military officials, some of them close allies of Putin, were beginning to perceive such ventures as part of the American plan to weaken the country. The military’s political champion was Putin, who decided in 2011 to run for president again, replacing his protege Medvedev after a single term in office.

“Putin had come to the point where he felt it was no longer necessary to cooperate,” Lugar said, “and it might even be demeaning to Russia.”

© Mikhail Metzel/Associated Press Russian President Vladimir Putin meets Secretary of State Hillary Clinton on her arrival at the APEC summit in Vladivostok, Russia.

Regression

In December 2011, despite a deepening economic crisis, Putin’s United Russia party retained control of the Duma in parliamentary elections that independent monitoring groups described as fraudulent.

Thousands of Russians took to the streets in protest, and Clinton — with the White House’s explicit blessing — spoke publicly in their defense, condemning Russian officials for manipulating the vote and systematically harassing election observers.

“The Russian people, like people everywhere, deserve the right to have their voices heard and their votes counted,” Clinton said during a speech that month in Lithuania. “And that means they deserve fair, free, transparent elections and leaders who are accountable to them.”

After her speech, when demonstrations in Moscow grew still larger, Putin suggested that his political opponents were following marching orders from Clinton and her team.

Opposition parties “heard the signal, and with the support of the U.S. State Department began active work,” Putin said. Kremlin officials repeated the charge in private meetings with U.S. diplomats, expressing a vehemence that surprised some Obama administration officials.

Even before the protests — and his own reelection as president in March 2012 — Putin had begun signaling the return of a more authoritarian and aggressive Russia. Beginning in late 2011, the Russian government would adopt policies stifling political dissent at home and increasing pressure on the former Soviet republics, from the Baltic to the Caucasus to Ukraine.

Clinton began privately warning the White House on how Putin’s return could affect a wide range of U.S. foreign policy priorities, such as promoting democracy in Eastern Europe and containing a Syrian civil war that was beginning to ignite sectarian violence and jihadist fervor throughout the Middle East.

She “argued that we were in for a rougher patch and needed to be clear-eyed about that,” said the senior U.S. official who worked for Republican and Democratic administrations. “It was a very honest analysis of the fact that, whatever hopes some people had early on for a more durable partnership, it just wasn’t going to happen.”

In fact, things fell apart with surprising speed. In 2012, Putin abruptly halted Russia’s participation in the Nunn-Lugar program. That same year, he expelled the U.S. Agency for International Development from Russia, charging interference in domestic affairs and ending USAID’s multimillion-dollar support for Russian civil society organizations.

Putin then repeatedly blocked U.S.-led efforts to resolve Syria’s civil war, insisting on preserving the presidency of Assad, a close Russian ally. Two years later — well after Clinton had left office — Putin stunned the world by snatching the Crimean Peninsula from Ukraine, something he had first threatened to do nearly a decade earlier.

Yet, while each of those actions was consistent with Putin’s combative style, Russia’s disputes with the Obama administration took on a more personal tone after 2011, several current and former U.S. officials and Russian policy experts said.

Today, with Clinton now aiming for the White House, it’s not surprising that Putin might support clandestine efforts to undermine her candidacy — regardless of his views of her chief political opponent, the officials and experts said.

“Putin has kind of got it in for Hillary,” said Clifford Kupchan, chairman of the consulting firm Eurasia Group and a Russia expert who attended private meetings with Putin during the Clinton years. “The statements after the Duma riots were like kerosene on a fire, and it really made Putin angry.”

Putin last week denied taking sides in the U.S. presidential race and he scoffed at allegations of Russian involvement in the hacking of Democratic officials’ email accounts, a crime that U.S. intelligence agencies believe was instigated at the highest levels of the Russian government.

Kupchan said he thinks that Russia’s role in the hacking, if verified, was “more about sowing some chaos in the U.S. system than about any real hope of Trump winning.” But he said it also reflects a shot across Clinton’s bow, as her record suggests that she would be both tougher and more outspoken on Russia compared to her predecessor.

“It may well be useful that she has a tough image,” he said. “Mrs. Clinton has been through the same journey that a lot of us have gone through on Russia, which is dashed hopes.”

When it comes to Putin’s Russia, he said, “she doesn’t wear deeply tinted sunglasses of any kind.”