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WASHINGTON — Petro O. Poroshenko was still the president of Ukraine earlier this year when his team sought a lifeline. With the polls showing him in clear danger of losing his re-election campaign, some of his associates, eager to hold on to their own jobs and influence, took steps that could have yielded a signal of public support from a vital ally: President Trump.
Over several weeks in March, the office of Ukraine’s top prosecutor moved ahead on two investigations of intense interest to Mr. Trump. One was focused on an oligarch — previously cleared of wrongdoing by the same prosecutor — whose company employed former Vice President Joseph R. Biden Jr.’s son. The other dealt with the release by a separate Ukrainian law enforcement agency to the media of information that hurt Mr. Trump’s 2016 campaign.
The actions by the prosecutor, Yuriy Lutsenko, did not come out of thin air. They were the first visible results of a remarkable behind-the-scenes campaign to gather and disseminate political dirt from a foreign country, encouraged by Mr. Trump and carried out by his personal lawyer, Rudolph W. Giuliani. In the last week their engagement with Ukraine has prompted a formal impeachment inquiry into whether the president courted foreign interference to hurt a leading political rival.
The story of how Mr. Trump and Mr. Giuliani operated in Ukraine has emerged gradually in recent months. It was laid out in further detail in the past week in a reconstructed transcript of Mr. Trump’s phone call this summer with a new Ukrainian president and in a complaint filed by a whistle-blower inside the United States government.
Along with documents and interviews with a wide variety of people in Ukraine and the United States, the latest revelations show that Mr. Trump and Mr. Giuliani ran what amounted to a shadow foreign policy in Ukraine that unfolded against the backdrop of three elections — this year’s vote in Ukraine and the 2016 and 2020 presidential races in the United States.
Despite the findings of United States intelligence agencies and the Justice Department that Russia was responsible for interfering in the 2016 election, Mr. Trump was driven to seek proof that the meddling was linked to Ukraine and forces hostile to him, even fixating on a fringe conspiracy theory suggesting that Hillary Clinton’s missing emails might be found there.
Backed by Mr. Trump, Mr. Giuliani, who once aspired to be secretary of state, sought to tar Mr. Biden with unsubstantiated accusations of impropriety, while he and associates working with him in Ukraine on the president’s agenda pursued their own personal business interests.
With the political landscape scrambled by Mr. Poroshenko’s defeat in April and the arrival of a new cast of Ukrainian officials, the approach pursued by Mr. Giuliani and Mr. Trump undercut official United States diplomacy.
And the signals sent by Mr. Trump — long skeptical of the strategic value of backing Ukraine against Russia, its menacing neighbor to the east — complicated efforts by the new Ukrainian government to fortify itself against Moscow.
The intensifying overlap this summer between Mr. Trump’s political agenda in Ukraine and his official foreign policy apparatus is now at the center of an impeachment inquiry that will examine whether the president of the United States directed or encouraged his subordinates to lean on a vulnerable ally for personal political gain.
Among the subjects covered in a subpoena sent Friday by House Democrats to Secretary of State Mike Pompeo and demands for depositions from American diplomats was Mr. Trump’s decision to freeze a $391 million military aid package to Ukraine this summer not long before his July 25 call with Ukraine’s new president, Volodymyr Zelensky, who defeated Mr. Poroshenko this spring.
Democrats are also looking into the recall in the spring of the United States ambassador to Kiev, Marie L. Yovanovitch, a career foreign service officer who was seen as insufficiently loyal to Mr. Trump by some of his conservative allies. On Friday evening, the State Department’s special envoy for Ukraine, Kurt Volker, abruptly resigned, not long after receiving a summons from House Democrats to sit for a deposition in the coming week.
Mr. Trump has dismissed the impeachment investigation as another “witch hunt.”
In an interview on Friday, Mr. Giuliani defended his efforts to push the Ukrainians to investigate Mr. Biden, his son, Hunter Biden, and others. He asserted that he was not doing it to try to influence the 2020 presidential election, though Mr. Biden is a leading contender for the Democratic nomination to challenge Mr. Trump.
“I was doing it to dig out information that exculpates my client, which is the role of a defense lawyer,” he said.
In the months before the steps taken in March on the politically explosive investigations sought by Mr. Trump, Mr. Giuliani had met at least twice with the man who would become a central figure in his efforts and a target of criticism in both countries: Mr. Lutsenko, 54, Ukraine’s top prosecutor.
First at a meeting in New York and later in Warsaw, Mr. Giuliani pushed Mr. Lutsenko for information about — and investigations into — a pair of cases of keen interest to his client.
They included the Bidens’ activities in Ukraine and the release during the 2016 campaign of incriminating records about Paul Manafort, Mr. Trump’s campaign chairman. Mr. Giuliani said early this year he had become increasingly convinced that the Manafort records were doctored and disseminated by critics of Mr. Trump to sabotage his campaign, and later used to spur the special counsel’s investigation into Russian interference in the 2016 election.
No evidence supports this idea and Mr. Manafort’s own retroactive filings under the Foreign Agents Registration Act corroborated the Ukrainian documents, which also matched financial records in the United States.
Still, it was not long before Mr. Trump, sensitive to any questions about the legitimacy of his 2016 victory, began echoing Mr. Giuliani’s language about what they viewed as the Ukrainian origins of the Russia investigation.
But Mr. Trump and Mr. Giuliani had also taken a growing interest in the role played by Mr. Biden, as vice president, in the dismissal of a previous Ukrainian prosecutor who had oversight of investigations into an oligarch who had served in a previous Ukrainian government and whose company had employed Hunter Biden. No evidence has surfaced that the former vice president intentionally tried to help his son by pressing for the dismissal of that prosecutor, whose ouster was being sought by other Western governments and institutions concerned about corruption in the Ukrainian government.
In their first meeting, in January, Mr. Lutsenko later told people, Mr. Giuliani called Mr. Trump and excitedly briefed him on the discussions. And once Mr. Lutsenko’s office took procedural steps to advance investigations involving the Manafort records and the oligarch linked to Hunter Biden, Mr. Giuliani, Mr. Trump and their allies aggressively promoted stories about the developments to conservative journalists at home, further turning a foreign government’s action to the president’s advantage.
“As Russia Collusion fades, Ukrainian plot to help Clinton emerges,” Mr. Trump wrote on Twitter in March, echoing the headline of one of the first such pieces by a Trump-friendly journalist.
Mr. Giuliani had seemed to slide eagerly into his new role. After his hopes of becoming secretary of state were dashed — in part, former administration officials said, because of his extensive foreign business ties — he became a personal lawyer for Mr. Trump when the president came under scrutiny by the special counsel, Robert S. Mueller III.
Mr. Trump was publicly lobbying his own Justice Department for an investigation of Mrs. Clinton and other Democrats. When he got no satisfaction on that score, Mr. Giuliani volunteered to take on the role of independent investigator, empowered by nothing other than Mr. Trump’s blessing.
Mr. Giuliani rejected the suggestion that he was interfering in the execution of American foreign policy, noting that Mr. Volker and the State Department eventually helped connect him with a top aide to Mr. Zelensky.
“If they were concerned, I don’t think they would ask me to handle a mission like this that’s sensitive,” he said. “I feel perfectly comfortable with what we did in Ukraine.”
Ukraine was familiar ground to Mr. Giuliani, a former New York City mayor and presidential candidate who had built a thriving consulting and security business.
Mr. Giuliani’s activity on behalf of Mr. Trump allowed him to maintain, and increase, his marketability to prospective clients around the world. Hiring him came to be seen as a way to curry favor with the Trump administration.
That perception has been fed in Ukraine by the dual roles played by some of his business associates. Chief among them is a Ukrainian-American businessman named Lev Parnas. Mr. Parnas gathered information on the ground in Kiev about the Bidens and the Manafort documents, and he helped connect Mr. Giuliani with Mr. Lutsenko and other Ukrainians with information about the cases that interested Mr. Trump.
But Mr. Parnas also has advised Mr. Giuliani on energy deals in the region, and pursued energy deals of his own in Ukraine, while presenting himself as a representative of Mr. Giuliani on the Trump-related matters.
In the early spring, as he was helping Mr. Giuliani in Ukraine, Mr. Parnas pitched a deal to the chief executive officer of the Ukrainian government-owned gas company, Naftogaz. Mr. Parnas also advised Mr. Giuliani on an effort related to a methane project in Uzbekistan for which Mr. Giuliani and his associates were to be paid at least $100,000.
Mr. Giuliani said the project in Uzbekistan did not pan out.
Mr. Parnas, a donor to Mr. Trump, rejected the suggestion that his efforts to assist Mr. Giuliani in Ukraine were related to his business, explaining in an interview on Saturday that he was funding them himself because “I think it’s outrageous that our president is getting blamed for things that he had nothing to do with.”
Mr. Parnas said he has not done business with Mr. Giuliani in years, that his discussions with Naftogaz did not yield a deal, that he had no involvement in the Uzbekistan effort, and in fact urged Mr. Giuliani to avoid doing business there.
Mr. Giuliani’s business in Ukraine dates to 2004, when he said he was invited to give a speech there. In 2008, one of his companies consulted for Vitali Klitschko, a former boxing and kickboxing champion who lost a bid that year to become mayor of Kiev, Ukraine’s capital, but was elected mayor in 2014.
Mr. Giuliani said he no longer represents Mr. Klitschko, but still advises him informally. He chastised the new president, Mr. Zelensky, this month for moving to limit the authority of Mr. Klitschko, who had endorsed Mr. Poroshenko in this year’s election.
“Reducing the power of Mayor Klitschko of Kiev was a very bad sign particularly based on the advice of an aide to the President of Ukraine who has the reputation of being a fixer,” Mr. Giuliani wrote on Twitter.
Some of Mr. Giuliani’s work in Ukraine has found him on opposing sides in internal Ukrainian feuds.
In 2017, one of Mr. Giuliani’s companies signed a contract with Pavel Fuks, a wealthy Ukrainian-Russian developer who was among the many Ukrainians seeking access in Mr. Trump’s Washington. The contract was to help Mr. Fuks attract investment from the United States to his hometown, Kharkiv, Ukraine.
A guide to the key figures and dates as President Trump and his allies pressured Ukraine to investigate his political opponents.
At the time, Mr. Fuks and others, including Sam Kislin, a Ukrainian-American businessman with ties to Mr. Giuliani, had become entangled in a complicated $1.5 billion deal to buy Ukrainian government bonds.
Mr. Lutsenko, the prosecutor, blocked the deal and seized the bonds by raising accusations of fraud. Mr. Kislin responded with suggestions that Mr. Lutsenko acted illegally.
Ukrainian media reported that the United States revoked Mr. Lutsenko’s visa for a time amid this dispute, though Mr. Lutsenko denied it. By January, he was able to travel to America, where he met with Mr. Giuliani to discuss investigating the Democrats.
Mr. Lutsenko’s eagerness to assist Mr. Giuliani was seen in some quarters in Kiev as an effort to win influential support to resolve his visa problem, fend off Mr. Kislin’s claims and secure American protection against potential political targeting in Ukraine.
Mr. Giuliani said he was not being paid for his work for Mr. Trump. He said he does not have any active projects at the moment in Ukraine, and that his connection to the president was not helping his business. “I don’t perceive it being down because I represent Trump, nor do I see a tremendous boost because I represent Trump,” he said.
When Mr. Lutsenko was pursuing the matters sought by Mr. Giuliani in the spring, people around Mr. Poroshenko thought it might elicit a show of support for him from Mr. Trump, who had boosted the election prospects of other foreign leaders.
Or, if Mr. Poroshenko lost, the thinking in Kiev went, Mr. Trump might at least feel compelled to try to protect Mr. Lutsenko, the helpful prosecutor, from the fate that often befalls aides to defeated Ukrainian leaders: prosecution by the victors and possible jail sentences or exile. As the whistle-blower complaint pointedly noted, Mr. Zelensky had signaled during the campaign that he would replace Mr. Lutsenko if he won the election.
At first the strategy encouraged by Mr. Giuliani and pursued by Mr. Lutsenko seemed to be living up to those hopes.
Mr. Poroshenko’s allies were pleased when Mr. Trump’s associates, including the president’s son, Donald Trump Jr., and Mr. Giuliani, launched public attacks against one of Mr. Poroshenko’s perceived enemies, Ms. Yovanovitch, the United States ambassador to Ukraine.
That month, she had criticized Ukraine’s record on corruption, alluding to reports of vote-buying by Mr. Poroshenko and a rival candidate, and she was seen as an impediment to the investigations sought by Mr. Giuliani. Mr. Poroshenko’s allies told people that they interpreted the Trump allies’ attacks on her as a sign that the Trump team would reciprocate if the investigations into Mr. Trump’s rivals continued.
But Mr. Trump never delivered the signal of support Mr. Poroshenko’s team was hoping for, and Mr. Poroshenko lost his re-election campaign in a landslide to Mr. Zelensky, a political neophyte.
Mr. Poroshenko’s press service issued a statement Saturday denying he solicited help for his re-election campaign. “Any attempts to link the American scandal to Poroshenko is groundless and unjustified manipulation,” the statement said. “Poroshenko has never negotiated for U.S. support for himself, but for Ukraine.”
Mr. Zelensky told reporters on election night that he intended to replace Mr. Lutsenko, who had been accused of turning a blind eye to corruption, though he did not carry out the move until he formed a new government following parliamentary elections in July.
When Mr. Trump spoke by phone to the new Ukrainian leader on July 25, Mr. Trump went so far as to complain to Mr. Zelensky about the impending replacement of Mr. Lutsenko. “I heard you had a prosecutor who was very good and he was shut down and that’s really unfair,” Mr. Trump said during the call. “A lot of people are talking about that, the way they shut your very good prosecutor down.”
From the early days of Mr. Trump’s campaign, he questioned American policy toward Ukraine, a former Soviet state that had received substantial support from the United States and the European Union. In the wake of Russia’s annexation of Crimea from Ukraine in 2014, Mr. Trump asked why the United States was so committed to the principle that seizures of territory must be opposed.
Mr. Trump called the Obama administration’s move to sanction Russia over the annexation “very confrontational,” and said in an interview with The Times in March 2016 that “it didn’t seem to me like anyone else cared other than us,” invoking his longstanding criticism that American allies do not pay their share when it comes to protecting democracy around the world.
Mr. Trump would soon develop another issue with Ukraine: Mr. Manafort’s case, which he came to view as evidence that forces in Ukraine aligned with Democrats were out to get him.
When Mr. Zelensky, running on fighting corruption and Russia, won a lopsided victory in the presidential election on April 21, it only appears to have intensified Mr. Trump’s determination to find political advantage for himself in the country.
Within a few weeks of Mr. Zelensky’s victory, the American ambassador, Ms. Yovanovitch, was recalled, months ahead of schedule, amid the claims by Mr. Trump’s allies that she was undermining him.
Mr. Trump quizzed his aides on Mr. Zelensky, asking whether Mr. Zelensky would help him or hurt him.
“There was a friend-or-foe operation on,” said one senior United States intelligence official. “No one understood Zelensky.”
By May, according to the whistle-blower’s account, the Ukrainian leadership had been led to believe that a meeting or phone call between the two presidents would depend on “whether Zelensky showed willingness to ‘play ball’” on the political investigations.
The complaint does not identify who delivered this message to the Ukrainians. But the timing coincided with a visit to Kiev of an American delegation, led by the energy secretary, Rick Perry, for Mr. Zelensky’s inauguration. Mr. Trump had ordered Vice President Mike Pence to skip the inauguration, the whistle-blower complaint said.
When members of the delegation returned to Washington, they stressed to Mr. Trump the importance of supporting the new Ukrainian government early on, and urged the president to demonstrate his commitment by granting Mr. Zelensky the White House visit he craved.
Mr. Trump was not convinced, saying he thought all Ukrainian politicians were corrupt and, alluding to Mr. Manafort’s case, that the country had tried to take him down.
In the meantime, as the whistle-blower complaint notes, Mr. Lutsenko was seeking to remain in office under Mr. Zelensky, and was sending mixed signals about pursuing the case related to the oligarch on whose company board Hunter Biden sat.
But Mr. Zelensky would later decide to replace Mr. Lutsenko, cutting off Mr. Giuliani’s main point of access to the Ukrainian government.
It was against that backdrop that Mr. Zelensky dispatched one of his closest aides, Andriy Yermak, to open a line of communication with Mr. Giuliani.
During a trip to Washington in July, Mr. Yermak, over breakfast at the Trump International Hotel, asked Mr. Volker for a connection to Mr. Giuliani. Mr. Volker broached the idea to Mr. Giuliani over a separate breakfast days later, and Mr. Giuliani and Mr. Yermak were soon chatting by phone.
Yet, even as these discussions were ongoing, Mr. Trump personally ordered his staff to freeze more than $391 million in military assistance for Ukraine. The move, made with little explanation, puzzled and frustrated officials in the departments of defense and state, as well as members of Congress from both parties who viewed the assistance as critical to helping a close ally as it confronted Russia.
Days later, Mr. Trump and Mr. Zelensky had their fateful phone call. After reminding Mr. Zelensky of the assistance the United States has provided to Ukraine, Mr. Trump asked him to work with Attorney General William P. Barr on investigations into the Bidens and other matters, according to the reconstructed transcript. Among them was the unfounded conspiracy theory suggesting that Ukraine rather than Russia was behind the hack of the Democratic National Committee emails in 2016 and that Mrs. Clinton’s missing emails might be on a server in Ukraine.
He also repeatedly asked Mr. Zelensky to work with Mr. Giuliani.
Mr. Zelensky assured Mr. Trump that “one of my assistants spoke with Mr. Giuliani just recently and we are hoping very much that Mr. Giuliani will be able to travel to Ukraine and we will meet once he comes to Ukraine.”
The day after the call, Mr. Volker and the United States ambassador to the European Union, Gordon D. Sondland, were in Kiev meeting with Mr. Zelensky. A week later, Mr. Giuliani and Mr. Yermak met face to face in Madrid.
Mr. Trump then raised eyebrows in August when he called for ending President Vladimir V. Putin’s pariah status on the global stage by readmitting Russia to the Group of 7 industrialized nations. Mr. Trump has quietly been urging a deal to reduce tensions between Ukraine and Russia that would pave the way for a removal of Western sanctions on Moscow, long a goal of Mr. Putin’s.
Mr. Trump himself hinted that was his goal when asked about Mr. Zelensky two weeks after the July 25 call. “I think he’s going to make a deal with President Putin, and he will be invited to the White House,” Mr. Trump told reporters.
In response to an approaching hurricane, Mr. Trump canceled a Sept. 1 trip to Warsaw at which he would have met Mr. Zelensky in person for the first time, instead sending Mr. Pence, who told reporters that he and Mr. Trump “have great concerns about issues of corruption,” linking them to the delayed military assistance.
Only after a bipartisan outcry did the White House release the assistance this month.
After hearing on Friday that Mr. Pompeo’s records had been subpoenaed in the impeachment investigation, some State Department officials said they hoped to learn why a career foreign service officer was recalled as ambassador, and whether Mr. Pompeo was complicit in — or had opposed — putting Mr. Giuliani in touch with Ukrainian officials.
Mr. Zelensky is still waiting for his White House meeting, as he noted when he finally met with Mr. Trump on Wednesday in New York.
“I want to thank you for the invitation to Washington,” Mr. Zelensky said at a joint news conference, “but I think you forgot to tell me the date.”
Kenneth P. Vogel and David E. Sanger reported from Washington and Andrew E. Kramer from Kiev. Mark Landler contributed reporting from London, Matina Stevis-Gridneff and Steven Erlanger from Brussels and Maria Varenikova from Kiev.
A version of this article appears in print on , Section A, Page 1 of the New York edition with the headline: A Shadow Foreign Policy Backfires on the President. Order Reprints | Today’s Paper | Subscribe