As Rudolph W. Giuliani comes under intensifying scrutiny for his efforts to overturn the 2020 election results, another legal threat is quietly fading: the criminal inquiry into his ties to Ukraine during the presidential campaign.
The investigation, conducted by federal prosecutors in Manhattan and the F.B.I., has examined whether Mr. Giuliani illegally lobbied the Trump administration on behalf of Ukrainian officials who helped him impugn Joseph R. Biden Jr., then expected to be the Democratic presidential nominee.
But after nearly three years, that inquiry into Mr. Giuliani, the former personal lawyer to Donald J. Trump, is unlikely to result in charges, two people with knowledge of the matter said.
While prosecutors had enough evidence last year to persuade a judge to order the seizure of Mr. Giuliani’s electronic devices, they did not uncover a smoking gun in the records, said the people, who spoke on the condition of anonymity to discuss a federal investigation.
The prosecutors have not closed the investigation, and if new evidence were to emerge, they could still pursue Mr. Giuliani. But in a telling sign that the inquiry is close to wrapping up without an indictment, investigators recently returned the electronic devices to Mr. Giuliani, the people said. Mr. Giuliani also met with prosecutors and agents in February and answered their questions, a signal that his lawyers were confident he would not be charged.
The Manhattan inquiry once posed the gravest legal danger to Mr. Giuliani, whose pressure campaign in Ukraine helped lead Mr. Trump to his first impeachment. But in recent weeks, as the Manhattan investigation has wound down, Mr. Giuliani’s efforts to keep Mr. Trump in power after the 2020 election have come under an increasingly harsh glare.
He has emerged as a key figure in the Georgia criminal investigation into attempts to overturn Mr. Trump’s loss in that state. Federal prosecutors also are examining his role in creating alternate slates of pro-Trump electors in several states, and he has been a central focus of the congressional investigation into the Jan. 6 attack on the Capitol.
The Manhattan inquiry reached further back in time to examine Mr. Giuliani’s entanglements with powerful Ukrainians in the run-up to the presidential election, when he blurred the line between his political goals and his business pursuits in ways that were highly unusual.
As he pushed Mr. Trump’s agenda in 2019, Mr. Giuliani developed ties to a Ukrainian oligarch under indictment in the United States, new interviews and documents show. Mr. Giuliani stayed in a five-star hotel and took a private flight courtesy of the oligarch’s company, an arrangement that has not been previously reported but was of interest to the Manhattan authorities, people with knowledge of the matter said. (Both men deny knowing about the travel payments, which were arranged by their associates.)
The investigators zeroed in on Mr. Giuliani’s relationship with Ukraine’s top prosecutor at the time, Yuriy Lutsenko, exploring whether Mr. Giuliani had illegally lobbied the Trump administration to oust the American ambassador to Kyiv at Mr. Lutsenko’s behest.
Mr. Lutsenko traveled to New York in January 2019, and met with Mr. Giuliani for hours, providing information that Mr. Giuliani hoped would damage Mr. Biden’s campaign. The next month, Mr. Giuliani considered accepting $200,000 from Mr. Lutsenko to retain both his firm and a husband-and-wife legal team to help recover funds believed to have been stolen from Ukrainian government coffers.
As the country’s top prosecutor, Mr. Lutsenko could provide what Mr. Giuliani and Mr. Trump desperately wanted — an announcement of an investigation into Mr. Biden and Burisma, the Ukrainian energy company that had paid his son Hunter as a board member. Mr. Lutsenko also wanted something: the removal of the American ambassador to Ukraine, Marie L. Yovanovitch, with whom he had butted heads. For weeks, Mr. Giuliani urged the Trump administration to remove her, and in April 2019 she was recalled.
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It is against federal law to try to influence the U.S. government on behalf of a foreign official without registering as a foreign agent, although prosecutions are relatively rare. Mr. Giuliani has maintained that he took aim at the ambassador simply because he believed she was disloyal to Mr. Trump and hostile to his attempt to find information about Mr. Biden.
That argument — that he was working solely in his capacity as the president’s lawyer, not for Mr. Lutsenko — could have undercut the central premise of a criminal case against him.
Mr. Giuliani ultimately abandoned the potential $200,000 deal with Mr. Lutsenko, another challenge to building a criminal case. Violating the lobbying law does not require money to change hands, but the absence of an obvious quid pro quo might not have sat well with a jury.
Spokesmen for the U.S. attorney’s office in Manhattan and the Federal Bureau of Investigation declined to comment on the investigation.
The authorities in Manhattan also briefly scrutinized Mr. Giuliani’s ties to the Ukrainian oligarch, Dmitry Firtash, people with knowledge of the matter said.
A New York Times review of documents and text messages and interviews found that Mr. Firtash’s company covered tens of thousands of dollars of Mr. Giuliani’s travel expenses in the summer of 2019, including his stay in the luxury hotel and private jet flight.
The travel payments did not appear to break any laws, but they show that Mr. Giuliani’s connection to Mr. Firtash was greater than has been publicly known.
“Rudy Giuliani had no idea that Firtash was paying for those trips,” said Robert J. Costello, Mr. Giuliani’s lawyer, adding that “he certainly would not have allowed it if he had known.”
Both Mr. Costello and a lawyer for Mr. Firtash, Lanny J. Davis, said their clients never spoke. “As far as Mr. Firtash knew, he never paid for or authorized any funds to be paid for Giuliani,” Mr. Davis said. The lawyer blamed the payments on “an inadvertent error” by one of Mr. Firtash’s administrative assistants, who he said did not notice Mr. Guiliani’s expenses amid other travel costsand paid for them “without Mr. Firtash’s knowledge or authority.”
Mr. Firtash was charged in the United States in 2013 with conspiring to bribe officials in India and has been fighting extradition while strenuously denying the charges. Mr. Giuliani considered representing Mr. Firtash in his extradition case but has said he quickly rejected the idea.
Mr. Firtash’s history in Ukraine, where he made a fortune in the energy business and publicly attacked Mr. Biden’s policies toward the country, appeared to have put the oligarch on Mr. Giuliani’s radar as he looked for dirt about Mr. Biden.
Mr. Giuliani began contacting Mr. Firtash’s lawyers in June 2019 seeking information about corruption in Ukraine, around the time Mr. Trump was pressing Ukraine’s president, Volodymyr Zelensky, to investigate the Bidens. Mr. Firtash’s lawyers told Mr. Giuliani they did not know of anything relevant.
There is no indication Mr. Firtash assisted Mr. Giuliani in his attacks on the Bidens, and Mr. Davis said the oligarch “categorically denies ever helping Giuliani or anyone else in any effort to dig up dirt.”
Even so, in the summer of 2019, an associate of Mr. Giuliani, Lev Parnas, met with the oligarch and recommended he add new lawyers to his team, the husband and wife, who were helping Mr. Giuliani dig into the Bidens. Mr. Parnas was paid to serve as their interpreter, and Mr. Firtash agreed to pay for some of Mr. Parnas’s travel expenses.
The offer seemed ideal. Around this time, Mr. Giuliani was preparing to go to London, and wanted to determine who would cover his travel. “Running into money difficulties on trip to London,” Mr. Giuliani wrote to Mr. Parnas in a text message.
During the trip in late June, Mr. Giuliani met in a hotel conference room with some Firtash associates, including a banker whose cousin was a Burisma executive.
Mr. Davis said the purpose of the meeting was to discuss Mr. Firtash’s contention that his extradition was politically motivated, and his associates did not talk about Burisma. The oligarch’s associates did not seek Mr. Giuliani’s help, Mr. Davis added.
That day, Mr. Giuliani upgraded hotels to the Ritz London. Mr. Firtash’s company, Group DF, later covered the roughly $8,000 stay, interviews and records show. The next month, the company paid $36,000 for a private flight Mr. Giuliani took from the Dominican Republic to Washington. And that August, Mr. Giuliani traveled with a friend and a bodyguard to Spain at a cost of more than $30,000, an expense that was listed on an invoice to a Group DF assistant and a longtime adviser to Mr. Firtash.
Mr. Costello said that Mr. Giuliani “doesn’t know how it came about.”
Mr. Davis said his client, Mr. Firtash, approved payments only to Mr. Parnas — “and never for any of Mr. Giuliani’s expenses.”
That October, Mr. Giuliani planned to fly overseas, but an unforeseen development arose: the arrests of Mr. Parnas and an associate, Igor Fruman, on federal campaign finance charges.
Mr. Parnas, who had witnessed Mr. Giuliani’s interactions with Mr. Lutsenko, has said he offered to cooperate with the investigation, but prosecutors opted to take him to trial, where he was convicted last year. And although Mr. Fruman pleaded guilty, he did not cooperate against Mr. Giuliani.
Reporting was contributed by Masha Froliak, Michael Rothfeld, Maria Varenikova and Kenneth P. Vogel. Susan C. Beachy contributed research.