Rudolph W. Giuliani spent months cultivating current and former prosecutors in Ukraine with a particular goal: Help President Trump in next year’s election by ensuring that Ukrainian authorities pursued allegations that could damage his Democratic rivals.

But the effort hit a snag. Political neophyte and comedian Volodymyr Zelensky — who once played a Ukrainian president on a television sitcom — swooped in last spring and became the president of Ukraine for real. Some of Giuliani’s efforts were thrown in doubt. One of the prosecutors Giuliani initially saw as an ally made public comments undermining his claims against former vice president Joe Biden. How Zelensky would act was unknown.

“New Pres of Ukraine still silent on investigation of Ukrainian interference in 2016 election and alleged Biden bribery of Pres Poroshenko,” Giuliani tweeted on June 21, without evidence of the allegations, referring to the former president, Petro Poroshenko, whom Zelensky defeated. “Time for leadership and investigate both if you want to purge how Ukraine was abused by Hillary and Obama people.”

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The frustration helps explain why Trump, ahead of a July 25 phone call that is now the subject of a whistleblower complaint and a congressional impeachment inquiry, turned up the heat.

Facing doubt about Zelensky’s willingness to work with Giuliani, Trump suspended military aid to Ukraine on July 18. Days later, Zelensky’s party swept Ukraine’s parliamentary elections, ushering in political newcomers and upping the uncertainty about whether Giuliani’s efforts would come undone.

In the meantime, Trump was withholding a date for a coveted bilateral summit with Zelensky. A congratulatory call with the comedian landed on the books — a chance for Trump to make his wishes clear.

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“I would like you to do us a favor though because our country has been through a lot and Ukraine knows a lot about it,” Trump said after Zelensky raised the matter of military aid, according to a rough transcript of the call released by the White House.

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Trump told the Ukrainian leader that he should coordinate with Giuliani and Attorney General William P. Barr in investigating the Democratic National Committee’s email server, which Trump suggested was in Ukraine, and probe the activities of Joe Biden and his son Hunter, who served on the board of a Ukrainian gas company while his father was vice president.

The sequence of events is at the heart of an extraordinary whistleblower complaint from an unnamed U.S. intelligence official released Thursday, which warns that Trump was using the power of his office to solicit interference in the 2020 election from Ukraine. Giuliani’s in-person meetings and secretive sessions form a key component of what the whistleblower saw as “a serious or flagrant problem, abuse or violation of law or Executive Order.”

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Giuliani decried any scrutiny of his conduct in a long interview Thursday, saying that more attention was finally being paid to the Biden family.

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“These crooks can go after me all they want,” he said. “They’re not going to find anything.”

A bevy of prosecutors

In interviews with The Washington Post, Giuliani said that, in his capacity as Trump’s personal lawyer, he had met with five current and former Ukrainian prosecutors since last year. During those meetings, he said, he obtained information about Hunter Biden and what the former New York mayor has alleged was collusion between Democrats and Ukraine in the 2016 election.

Giuliani and a Ukrainian American businessman who was working with him, Lev Parnas, said those meetings included a Skype phone call last year with former Ukrainian prosecutor general Viktor Shokin, whom Joe Biden had urged be fired. Giuliani then met with then-Ukrainian Prosecutor General Yuri Lutsenko in New York in January and again in Warsaw in February. 

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By May, Giuliani planned to visit Kiev to meet with the newly elected Zelensky. After the New York Times revealed his plan, the former mayor canceled his trip but said he met in Paris with more prosecutors, including Nazar Kholodnytsky, head of Ukraine’s Specialized Anti-Corruption Prosecutor’s Office. So many Ukrainian prosecutors had to be consulted because they often disagreed with one another, Giuliani said, adding that some of them are “inept.” 

“It’s hard for me to separate all the different ones,” he said.

Some of the Ukrainians Giuliani and his associates interacted with were banned from entering the United States. Giuliani blamed the U.S. Embassy in Ukraine for blocking the officials from coming to the United States to give him more information.

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 Parnas described an atmosphere in which Ukrainian prosecutors were rushing to Giuliani with information, often also pursuing their own personal and political agendas. He described the officials as “hitting on every door to try and get their information here.”

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A former Ukrainian prosecutor said he believed the officials were angling to provide Giuliani with compromising information at least partly to advance their own careers — and win U.S. backing for their position within the often rough-and-tumble world of Ukrainian politics.

“They needed direct access to the U.S. president to convince him that they are the right group to represent Ukraine,” the former prosecutor said, speaking on the condition on anonymity to discuss his private impressions of the group’s motivations. “They understood the best method to come closer to Trump is to bring something that contains information that is a real interest to U.S. politics.”

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Who contacted whom in each case, and how, is not entirely clear. 

Giuliani and Parnas suggested that the prosecutors came to them. Lutsenko, however, in an interview with The Post on Thursday, said Giuliani contacted him via another prosecutor, whom the Ukrainian politician declined to name.

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In an interview in his heavily guarded office in Kiev, Kholodnytsky said that his conversation with Giuliani in Paris was like that between two prosecutors. The Ukrainian official voiced his suspicions about investigations into Burisma, the energy company on whose board Hunter Biden sat for five years, and about the summer 2016 appearance in Ukraine of a black ledger tallying payments to Paul Manafort, Trump’s campaign chairman, that forced him out of his post.

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“The conversation was generally about corruption in Ukraine,” Kholodnytsky said. “I had a personal conversation. I told him that something wasn’t right there.” 

Giuliani “didn’t react,” Kholodnytsky said. “He didn’t jump with balloons.”

Changing stories

Among the bevy of prosecutors, perhaps none was more important than Yuri Lutsenko, who served as Ukraine’s top prosecutor under Poroshenko from May 2016 until Aug. 29 of this year. 

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Lutsenko was always an unconventional pick for the post. Although he served twice as interior minister after the 2004 Orange Revolution, he was not a lawyer, a typical qualification for a job comparable to attorney general in the United States.

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When he took office in 2016, diplomats and pro-Western activists were hopeful that he could sweep through the corruption-plagued prosecutor general’s office and shake up the system. Biden had just helped to push out his predecessor, Viktor Shokin, amid a widespread perception in Ukraine and among its Western backers that he was perpetuating old, corruption-prone habits. 

But hopes placed in Lutsenko were quickly dashed. He clashed with a more independent anti-corruption bureau set up in the aftermath of a 2014 pro-Europe uprising. He also ended up in a vicious battle with U.S. Ambassador Marie Yovanovitch, who pushed him to stop pressuring the bureau. She called for Kholodnytsky’s ouster after the bureau allegedly caught him on tape advising suspects in corruption cases on how to avoid prosecution — a bold intervention on her part.

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By the time he met Giuliani, Lutsenko was fed up with Yovanovitch, a career diplomat who was appointed in the final year of the Obama administration. He was nervous about his future as Ukrainian presidential elections drew closer. And he saw a chance to deliver a blow to the rival anti-corruption bureau that he viewed as a dangerous actor with loyalties more to the United States than to Ukraine.

Initially, Lutsenko appeared to help in Giuliani’s pursuit. 

He stirred up perceptions that Joe Biden had intervened into Ukraine’s justice system to quash an investigation into the gas company where Hunter Biden served on the board, meeting repeatedly with Giuliani and telling a conservative columnist at the Hill newspaper that he “would be happy” to talk to Barr about the issue. 

But when Poroshenko, his boss and political ally, lost in the spring election, the top prosecutor dialed back certain comments.

First, in May, he said in an interview with Bloomberg News that “at least as of now,” he didn’t believe that the Bidens had broken any Ukrainian laws.

Then on Thursday, he declared to The Post that “on the territory of Ukraine, Hunter Biden did not violate Ukrainian legislation.”

Giuliani was livid. “He flipped because he was trying to protect Poroshenko,” he said in an interview Thursday.

'Bad news'

Giuliani wanted to go through every point that could potentially boost Trump’s reelection effort, the former top prosecutor recalled.

“He had a lot of files and documents on the table. I was not the first person he had met with about the case,” Lutsenko said.

One of Giuliani’s main allegations is that Joe Biden pushed for Shokin’s dismissal because the prosecutor was investigating the owner of the gas company where Hunter Biden was on the board. The U.S. ambassador at the time, however, had publicly pressured Shokin to pursue the owner, singling out the prosecutor’s apparent shelving of the case as an example of his failures.

For Lutsenko, discussions with Giuliani were a chance to take aim at Yovanovitch, who had a brass-knuckled approach to tackling the institutions and individuals she saw as keeping Ukraine stuck in a mire of corruption.

Giuliani also wanted her fired. “Her embassy was keeping five different people from giving us information,” he said.

Her blunt style led to clashes. But other Western diplomats in Kiev said her approach was fairly common for U.S. envoys in any country that depends heavily on U.S. aid.

Lutsenko said he confided his worries about the ambassador to Giuliani. In an article in the Hill, Lutsenko claimed the ambassador gave him a “do not prosecute” list — an allegation that the State Department denied. The story got play on Fox News and was mentioned by both Trump and his eldest son in tweets, building pressure that led to the State Department ending Yovanovitch’s tour early. Lutsenko, in an April interview with the Ukrainian publication the Babel, admitted she did not give him a list. Speaking to The Post, he maintained she wanted certain people to be untouchable.

Yovanovitch declined to comment.

In his call with Zelensky, Trump called her “bad news.” Zelensky said he agreed “100 percent.”

Trump added: “Well, she’s going to go through some things.”

Birnbaum reported from Kiev. Tom Hamburger in Washington and David L. Stern and Natalie Gryvnyak in Kiev contributed to this report.