“There’s nothing that happens in Ukraine you don’t know about,” Biden continued. “If something like this happens again, I’m done with you.”

The public humiliation of Poroshenko illustrated the unusually aggressive approach employed by Biden, the Obama administration’s chief Ukraine envoy, to bring the distant but strategically important former Soviet republic closer to the West. It was an approach that yielded successes but also earned Biden and his aides a slew of enemies and detractors in Ukraine, and it may now have boomeranged to hurt his 2020 presidential campaign.

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Biden’s actions unfolded over an extraordinary period of turmoil in Ukraine, as well as trauma in his own life. When Poroshenko took over as the country’s fifth president in mid-2014, there was hope that the man with the slogan “Live in a new way” would implement changes and unite the country against the Russian threat.

During the last three years of the Obama administration, Biden made five trips to Ukraine. He held at least 70 phone calls with Ukrainian leaders, the bulk of them with Poroshenko, and had meetings in Washington, Munich, and at the United Nations. He delivered a speech to the Ukrainian parliament, attended ceremonies and acted as an intermediary to the international community for Kyiv. He constantly urged the country to implement reforms, holding out U.S. financial assistance in return.

Biden and Poroshenko’s conversations continued even after Biden left office, through earlier this year.

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Poroshenko would typically call Biden to wish him happy birthday. When Biden’s son Beau died in 2015, Poroshenko was one of the first to call with condolences. And when Poroshenko came to Washington, Biden sent flowers to his wife.

Biden’s extensive involvement in the country’s fitful march toward reform has highlighted the political risks of becoming so deeply enmeshed in another country’s murky domestic affairs. The danger increased when Biden’s son Hunter took a paid position on the board of a Ukrainian gas company owned by a former government minister later accused of corruption. Though both Bidens say they did not discuss the gas company, the arrangement raised the perception that Biden’s family was benefiting from his vice-presidential role and gave ammunition to his critics, some of whom have now linked up with allies of Trump to smear the former vice president.

The relationship between the two leaders fractured over time in part because of Biden’s repeated demands on Poroshenko, to the point that Biden’s allies now view some of the unsubstantiated allegations of corruption leveled against Biden as fallout from his actions on behalf of the U.S. government. Those allegations have been stoked in part by two Poroshenko allies — former prosecutor general Viktor Shokin, whose firing Biden demanded, and his successor, Yuri Lutsenko. Both men coordinated with President Trump’s personal attorney, Rudolph W. Giuliani, earlier this year. The actions of those Ukrainian prosecutors in Poroshenko’s orbit have led to President Trump’s insistence on an investigation into the Bidens that lies at the heart of the impeachment inquiry.

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“The vice president’s pressure on Poroshenko dialed up: Stop with excuses, get things done,” said Jake Sullivan, who for a year and a half was Biden’s national security adviser. “Ultimately, I think for Poroshenko, the VP embodied the persistent pressure the U.S. put on him to do things he didn’t want to do. And his relationship with the VP suffered as a result of that.”

This story is based on interviews with nearly a dozen aides and officials in the United States and Ukraine, including representatives to both Biden and Poroshenko. Some would speak only on the condition of anonymity given the fraught nature of the relationship.

In early 2014, Ukraine was in turmoil. An uprising by Ukrainians demanding closer ties to Europe had led to the ouster of the country’s Russian-leaning government, followed closely by Russia’s invasion of its territory in Crimea. Biden had been tasked with overseeing efforts in a country that was teetering between Russian influence and a desire to be integrated with the European Union. It was a role made to order for Biden, raised politically during the Cold War and its aftermath.

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If he was sometimes wary of U.S. intervention, in this case Biden defined a broader rationale on behalf of the United States: dismantling the influence of Russia. The U.S. view was widely shared: European nations, the International Monetary Fund and the World Bank offered Ukraine aid, loan guarantees and political support, so long as the government in Kyiv implemented reforms to make Ukraine less corrupt and more economically stable.

As he grew further enmeshed during the spring of 2014, Biden took two trips there, first in April and then in June, for Poroshenko’s inauguration, where he walked the red carpet and grew optimistic that the allure of democracy could overcome autocracy.

Biden and Poroshenko met for three hours, far past the allotted time, the two men sitting across from each other at a table filled with five aides on each side. One was a lifelong politician who called himself “Middle Class Joe,” the other a Ukrainian oligarch-turned-president who was known as “Chocolate King” because of his confectionery company.

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“There was guarded optimism with Poroshenko, that he was perhaps someone who could run a more effective, cleaner government than his predecessors had,” said Sullivan, who accompanied Biden on those two trips. “He and the VP had a friendly, familiar rapport.”

Between Biden’s two springtime meetings, his son was appointed to a board seat at Burisma Holdings, the Ukrainian gas company whose owner was the subject of a money-laundering probe and would later be investigated on charges of corruption. The position, for which Hunter Biden made between $50,000 and $100,000 a month, was part of the company’s effort to burnish its credentials and send a message that it had access to powerful people in the West. There were multiple red flags at the time that his son’s involvement appeared to be a conflict of interest, but Biden took no action to discourage it.

Biden and Poroshenko began to clash as Biden continued pushing the Ukrainian president to do things he did not want to do, such as implement politically difficult reforms and push out some of his former allies.

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“Poroshenko undoubtedly was annoyed by always having to do these politically difficult things, and being asked by the U.S. to do it,” said Colin Kahl, who became Biden’s national security adviser in August 2014. “He was always trying to do the de minimis. Biden wasn’t naive. He knew as soon as you slacked off things would backslide.”

It was also a time of personal turmoil for Biden. His son Beau had been diagnosed with brain cancer in 2013, a crisis that those close to Biden said made him reluctant to criticize the decisions of Hunter Biden. By May 2015, when Beau Biden died, Hunter would be his only living son.

In early 2015, Poroshenko tapped Viktor Shokin as prosecutor general. U.S. officials pushed for more — for Ukraine to establish several anti-corruption agencies and courts, and new requirements for public disclosure about the finances of elected officials. They saw Poroshenko as a vehicle to help push for some of those reforms, but over time they came to believe he was an obstacle.

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Biden would persistently and forcefully raise questions on his calls with Poroshenko about the depth of his commitment to root out corruption, said Mike Carpenter, a former foreign policy adviser to Biden who was also deputy assistant secretary of defense for Russia, Ukraine, and Eurasia. “It was just excuses, excuses, excuses,” he said. “And it dragged for over a year. It just became more and more grating. It became obvious to us in Washington that the resistance was within Poroshenko’s inner circle.”

Both sides were frustrated, he said, but Biden “wasn’t moving on . . . he pressed each and every time for these reforms to be implemented. And that created friction in the relationship.”

In the fall of 2015, U.S. officials begin targeting Shokin specifically. Victoria Nuland, the assistant secretary of state, said during congressional testimony in October 2015 that the prosecutor general’s office needed to clean up corruption including the “dirty personnel” in its own office.

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“He became a single point of failure,” Kahl, Biden’s national security adviser, said of Shokin. “We could keep pushing corruption cases, but unless there was a fundamental change at the top, things weren’t going to change.”

Among the matters that had lain largely dormant under Shokin, according to U.S. officials and Ukrainian anti-corruption activists, was the earlier investigation into the former minister who owned Burisma, the Ukrainian gas company on whose board Hunter Biden served.

When Biden went to Ukraine in December 2015, he used a new piece of leverage to try to force Poroshenko to act. For the first time, he linked a $1 billion loan guarantee with Shokin’s firing.

“Look, you’re not getting this money unless Shokin is fired,” Biden told Poroshenko, according to Kahl.

As Biden approached his speech to Ukraine’s parliament, his advisers crafted two versions. One would announce the $1 billion loan guarantee as long as Shokin was removed, and the other would take on corruption. With Poroshenko still resistant, Biden and his aides gathered in a room and opened a laptop, reworking his speech just before he was scheduled to give it. They increased the degree to which Biden called for corruption crackdowns, attempting to ratchet up the pressure on Poroshenko to remove Shokin.

Biden aides at the time figured Poroshenko was reluctant to get rid of Shokin because Shokin had something on him. But Poroshenko was also aggravated with Biden, who kept pressing him to do politically difficult things.

It would take several more months — and a string of persistent calls from Biden — before Poroshenko removed Shokin. A few days later, Poroshenko arrived in Washington for a nuclear summit. He met with Biden, and Biden congratulated him. A deal on the $1 billion loan guarantee would soon be finalized.

Biden would later brag openly about the pressure he had applied and the threat he leveled over the loan guarantees, footage that one day would be used in an ad against him as supposed evidence of his own corruption. Biden’s public recounting of how he pressured Poroshenko to fire Shokin also came across in Kyiv as making the Ukrainian president look weak, like a marionette taking orders from Washington.

Pressure against Poroshenko, which usually took place behind closed doors, continued in 2016, most dramatically in the September blowout at the United Nations. But a few months later, three days before Donald Trump’s inauguration, Biden was in Ukraine for the last time. The Obama administration was on its way out, and any sense of urgency was gone.

“I may have to call you once every couple weeks just to hear your voice,” Biden told Poroshenko during a news conference. “This has been going on a long time.”

In a private meeting, recounted by a Biden aide who was there, Poroshenko indicated he was baffled by Trump and eager to figure out how to get on his good side. He asked Biden for advice on how to approach the new leader. Biden told Poroshenko that U.S. foreign policy was much broader than Trump; he urged him to engage with incoming defense secretary Jim Mattis, Vice President-elect Mike Pence and others in the administration who had opposed Russian aggression.

“I strongly urge the people of Ukraine: Keep demonstrating your commitment to the rule of law; keep fighting corruption; insist on transparency; investigate and prosecute government officials who siphon off public funds for their own enrichment,” Biden said during the news conference.

Several times in 2017, Poroshenko called Biden, at times soliciting advice about how to deal with the new administration. He also repeatedly invited Biden to Ukraine to receive an award.

“Biden was very cautious,” said Carpenter, who still works with Biden. “He didn’t want to step on the toes of the new administration. He took the calls, but he said, ‘Look, you need to establish a relationship with Trump and Pence. They’re in office now.’ ”

Biden called Pence to brief him on the contents of his calls with Poroshenko, according to Carpenter.

In his 2017 book, and in a speech he delivered in 2018 to the Council on Foreign Relations, Biden unflatteringly cast Poroshenko as an unwilling partner in moving Ukraine forward and, alternately, as someone he could bend to his demands.

Poroshenko was furious at the portrayals, according to people who spoke with him.

A spokeswoman for Poroshenko said in a statement that the Ukrainian leader had not considered his relationship with Biden ruined. She did not respond to other questions.

In January, Giuliani conducted interviews with Shokin, the prosecutor Poroshenko fired at Biden’s urging, and Lutsenko, his successor. Both stirred up perceptions that Biden had pushed for Shokin’s firing to quash investigations into the owner of Burisma, where Hunter Biden was on the board — a baseless allegation that Giuliani is peddling for political gain in the 2020 election. (In his interactions with the Ukrainian prime minister’s office, Biden never mentioned anything that could be considered personal, such as cases against Burisma, said a former Ukrainian official familiar with the interactions. The former official dismissed the idea that Shokin was fired over Burisma.)

Biden allies and some in Ukraine suspect that Lutsenko would not have met with Giuliani without the blessing of Poroshenko — who was his boss at the time. But Lutsenko has said he met Giuliani in a personal capacity and told Poroshenko only after the meeting, which came at a time when both men were fighting for political survival and eager for support from the Trump administration.

A month after Giuliani spoke with Lutsenko and Shokin, Biden went to the Munich Security Conference and had a private one-on-one meeting with Poroshenko. It is not clear what they discussed, but those who heard about the meeting described it as tense.

It is the last known time the two men spoke. In late April, Poroshenko conceded defeat in his race for a second five-year term to political neophyte and comedian Volodymyr Zelensky. Days later, Biden would announce his third bid for the presidency.