As Rudolph W. Giuliani waged a public campaign this year to unearth damaging information in Ukraine about President Trump’s political rivals, he privately pursued hundreds of thousands of dollars in business from Ukrainian government officials, documents reviewed by The New York Times show.
Mr. Giuliani, the president’s personal lawyer, has repeatedly said he has no business in Ukraine, and none of the deals were finalized. But the documents indicate that while he was pushing Mr. Trump’s agenda with Ukrainian officials eager for support from the United States, Mr. Giuliani also explored financial agreements with members of the same government.
His discussions with Ukrainian officials, including the country’s top prosecutor, who assisted him on the dirt-digging mission, proceeded far enough along that he signed at least one retainer agreement, on his company letterhead.
In an interview on Wednesday, Mr. Giuliani played down the discussions. He said that a Ukrainian official approached him this year seeking to hire him personally. Mr. Giuliani said he dismissed that suggestion, but spent about a month considering a separate deal with the Ukrainian government. He then rejected that idea.
“I thought that would be too complicated,” Mr. Giuliani said. “I never received a penny.”
Mr. Giuliani’s shadow diplomacy campaign in Ukraine on behalf of the president is a central focus of the current House impeachment inquiry.
At the same time, a federal criminal investigation into Mr. Giuliani is examining his role in the campaign to oust Marie L. Yovanovitch, the American ambassador to Ukraine, and scrutinizing any financial dealings he may have had with Ukrainian officials, according to people briefed on the matter.
Prosecutors and F.B.I. agents in Manhattan are scrutinizing whether Mr. Giuliani was not just working for the president, but also doing the bidding of Ukrainian officials who wanted the ambassador removed for their own reasons, the people said.
It is a federal crime to try to influence the United States government at the request or direction of a foreign government, politician or party without registering as a foreign agent. Mr. Giuliani did not register as one, he has said, because he was acting on behalf of his client, Mr. Trump, not Ukrainians.
Mr. Giuliani has not been accused of wrongdoing.
The federal inquiry focused on Mr. Giuliani grew out of the case against two of his associates, Lev Parnas and Igor Fruman, who were arrested on campaign finance charges last month. Alongside Mr. Giuliani, Mr. Parnas and Mr. Fruman worked to pressure Ukraine into announcing investigations into former Vice President Joseph R. Biden Jr. and his son Hunter.
Mr. Parnas and Mr. Fruman have pleaded not guilty to the campaign finance charges.
Spokesmen for the United States attorney in the Southern District of New York, Geoffrey S. Berman, whose prosecutors are handling the case, and the F.B.I. declined to comment.
The documents reviewed by The Times portray an evolving effort over the course of several months by Mr. Giuliani and lawyers close to him to consider taking on various Ukrainian officials or their agencies as clients.
The Times could not determine whether the documents it reviewed comprised the entirety of discussions between Mr. Giuliani and other lawyers about representing Ukrainian government officials.
In return, Mr. Giuliani would help the government recover money it believed had been stolen and stashed overseas, advising Mr. Lutsenko “on Ukrainian claims for the recovery of sums of money in various financial institutions outside Ukraine.”
The proposal came a few weeks after Mr. Giuliani met at his office in New York with Mr. Lutsenko to discuss Ukrainian corruption. Mr. Lutsenko told Mr. Giuliani and others about payments he claimed involved Mr. Biden, Hunter Biden and Burisma Holdings, a Ukrainian company that had named the younger Mr. Biden to its board, according to a memo summarizing the talks. Mr. Lutsenko also shared information he said he had about Ms. Yovanovitch.
Mr. Giuliani was critical of Ms. Yovanovitch, whom he and other Republicans have said was opposed to the president. Mr. Giuliani’s moves against her, however, were also aligned with the interests of Mr. Lutsenko, who had butted heads with the ambassador.
Ultimately, Ms. Yovanovitch was removed from her post in May, and Mr. Lutsenko was replaced in August after a new Ukrainian president took office.
In the interview, Mr. Giuliani said that after their meeting, Mr. Lutsenko broached the idea of hiring him to help deliver information about corruption in Ukraine to United States authorities.
Although Mr. Giuliani worked for free for Mr. Trump, he said he concluded that it would be a potential conflict of interest for him to represent the Ukrainian prosecutor in that capacity.
Still, he said, Mr. Lutsenko also wanted to hire Mr. Giuliani to help recover Ukrainian assets.
An updated proposal was circulated a few days later, along with instructions on how to wire money to Giuliani Partners. This version made no mention of Mr. Lutsenko, but instead sought $300,000 from the Ukrainian Ministry of Justice and the Republic of Ukraine. The proposal was signed by Mr. Giuliani, but not by the justice minister at the time, Pavlo Petrenko.
Asked why he signed that agreement and pursued payment, Mr. Giuliani said he considered the deal in order to learn more about the recovery of assets and money laundering in Ukraine.
“It did not come out of my desire to make a lot of money,” he said, adding that his typical retainer is much higher than a few hundred thousand dollars.
“Originally, I thought I would do it. And then when I thought it over,” he said, “I thought it would look bad.”
The Ukrainian Ministry of Justice said Wednesday that it did not enter into any contracts or make payments to Mr. Giuliani.
In March, a document proposed that the Ukrainian justice ministry would hire Ms. Toensing and Mr. diGenova for help with asset recovery. But it said that the General Prosecutor’s office, run by Mr. Lutsenko, would pay $300,000 to Giuliani Partners.
Several later draft retainer agreements involved Ms. Toensing and Mr. diGenova but did not reference Mr. Giuliani.
In April, Mr. Lutsenko reappeared as a potential client in some new versions of documents, along with one of his deputies. Under the proposals, which were signed only by Ms. Toensing and printed on her law firm’s letterhead, she and Mr. diGenova would represent the officials “in connection with recovery and return to the Ukraine government of funds illegally embezzled from that country.”
The proposed April agreement between Mr. Lutsenko and Ms. Toensing and Mr. diGenova also referenced another assignment: helping him meet with American officials about “the evidence of illegal conduct in Ukraine regarding the United States, for example, interference in the 2016 U.S. elections.”
Asked for comment by The Times, a spokeswoman for Mr. Lutsenko, Larisa Sarhan, on Wednesday referred to an interview Mr. Lutsenko gave to a Ukrainian news outlet confirming that aides to Mr. Giuliani had asked him to hire a lobbying company. He did not specify which company.
Mr. Lutsenko told Ukrainska Pravda he had been seeking a meeting with William P. Barr, the United States attorney general, and was in touch with unnamed advisers to Mr. Giuliani.
“In the end, they said the meeting would be impossible unless I hired a company that would lobby for such a meeting,” Mr. Lutsenko told the news outlet, adding that he declined to do that.
The proposals noted that Ms. Toensing and Mr. diGenova might have to register as foreign agents under American law.
“We have always stated that we agreed to represent Ukrainian whistle-blowers,” Mark Corallo, a representative for the law firm of Ms. Toensing and Mr. diGenova, said in a statement on Wednesday.
Mr. Corallo said the business proposals were “unaccepted” and the lawyers never represented the Ukrainians. “No money was ever received and no legal work was ever performed,” he said.
In another agreement signed by Ms. Toensing in April, the client would have been Victor Shokin, the top Ukrainian prosecutor before Mr. Lutsenko. Mr. Shokin was ousted after critics, among them Mr. Biden, said he was soft on corruption.
Mr. Shokin did not respond to a request for comment.
Mr. Shokin had also spoken with Mr. Giuliani and his associates in January, via Skype. In the call, Mr. Shokin asserted that American officials applied pressure on the Ukrainian government to kill an investigation of Burisma, and that he was fired after Mr. Biden accused the prosecutor of being corrupt, according to a memo summarizing the discussion.
Ms. Toensing proposed that, for $25,000 a month, her firm would represent Mr. Shokin “for the purpose of collecting evidence regarding his March 2016 firing as Prosecutor General of Ukraine and the role of then-Vice President Joe Biden in such firing, and presenting such evidence to U.S. and foreign authorities.”
The news of Mr. Giuliani’s efforts comes a day after Mr. Trump appeared to distance himself from Mr. Giuliani.
In an interview on Tuesday, the former Fox News host Bill O’Reilly asked Mr. Trump if he had directed Mr. Giuliani in his Ukraine efforts. “No, I didn’t direct him, but he is a warrior, he is a warrior,” Mr. Trump said.
When asked what work Mr. Giuliani was doing for him related to Ukraine, Mr. Trump replied, “You have to ask that to Rudy.”
Andrew E. Kramer, Maggie Haberman and Ken Vogel contributed reporting. Maria Varenikova contributed reporting from Kyiv.