In the last few months of the Trump administration, senior Justice Department officials have repeatedly tried to stop federal prosecutors in Manhattan from taking a a crucial step in his investigation of Rudolph W. Giuliani’s negotiations in Ukraine, delaying a search warrant for some of Giuliani’s electronic records, according to people with knowledge of the matter.
The actions of political appointees in the Washington Department of Justice effectively delayed the investigation as it was gaining momentum last year.
In the final months of 2020, prosecutors were still investigating whether Giuliani had illegally lobbied the Trump administration on behalf of Ukrainian authorities and oligarchs who helped him search for dirt in 2019 over Joseph R. Biden Jr., then a Democratic Candidate leader, said the people.
Giuliani denied any wrongdoing. His lawyer, Robert J. Costello, declined on Wednesday to comment “on media speculation.”
Unswervingly loyal to former President Donald J. Trump, Giuliani has been a central figure in both of the former President’s impeachments, first working on Trump’s behalf in Ukraine and then leading a campaign to reverse the election results that culminated in .6 demonstration shortly before Trump supporters violently invaded the Capitol.
Last summer, prosecutors and FBI agents in Manhattan were preparing to seek a search warrant for Giuliani’s records related to his efforts in Ukraine, said the people, who spoke on condition of anonymity because they were not authorized to discuss the investigation. In progress.
But first, investigators in Manhattan had to notify Justice Department officials in Washington, who must be consulted on search warrants involving lawyers because of concerns that prosecutors might inadvertently obtain confidential communications with clients. The warrant involving Mr. Giuliani was particularly sensitive because of his most important client – Mr. Trump.
While career officials at the Department of Justice in Washington broadly supported the search warrant, senior officials raised concerns that the warrant would be issued very close to the election, people with knowledge of the matter said.
In the 60 days leading up to an election, the Justice Department generally tries to avoid taking aggressive investigative actions that could affect the outcome of the vote if the actions were made public.
Manhattan prosecutors observed officials in Washington who initially raised the idea in the summer, before the 60-day cut, people said. And after the election, prosecutors tried again.
But even so, political appointees in the Trump Justice Department, including officials from the assistant attorney general’s office at the time, did not approve, noting that Trump was still contesting the election results in several states – a legal effort led by Mr. Giuliani, people said.
The opposition angered prosecutors in Manhattan and some career officials in Washington, who questioned whether senior officials were treating all politically sensitive investigations in the same way after the election. Although Manhattan prosecutors still faced opposition to examining Giuliani’s records, federal prosecutors in Delaware were allowed to issue subpoenas for a tax investigation into Biden’s son, Hunter Biden.
And while political nominees were skeptical that there was enough evidence to accuse Giuliani, the career officials involved felt that there was sufficient reason to believe that the search would result in evidence of a crime, the legal standard for obtaining a warrant.
Ultimately, senior officials in Washington proposed to postpone the decision on the subpoena until the Biden government took over. It is not clear whether prosecutors have obtained a warrant since Biden was sworn in.
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The episode was not the only time that the Trump Justice Department tried to intervene in a politically sensitive investigation by the United States Public Prosecutor’s Office in Manhattan, one of the most independent prosecutors’ offices in the country. In June, Trump fired office chief Geoffrey S. Berman, who oversaw a series of investigations into Trump’s allies, including Stephen K. Bannon.
CNN first reported on Wednesday that the potential search warrant met resistance from Justice Department officials in Washington, who questioned the strength of the evidence against Giuliani. In December, NBC News reported that Manhattan prosecutors discussed making a legal request for Giuliani’s electronic communications.
The Giuliani investigation focused on his dealings with Ukrainian officials and oligarchs who claimed to have damaging information about Biden’s son Hunter, who was on the board of a Ukrainian energy company, people said.
As part of that approach, federal prosecutors in Manhattan examined Giuliani’s ties to Dmitry Firtash, a Ukrainian oligarch who is being indicted in the United States, according to documents and people familiar with the matter.
Hoping to avoid extradition to the United States, Firtash hired two lawyers close to Giuliani to discuss his case at the highest levels of the Justice Department, while Giuliani sought Firtash’s help to collect negative information about the Bidens, these people said.
It is unclear whether the investigation will result in any charges against Giuliani, the former mayor of New York City and a former United States attorney in charge of the same office that is now examining his conduct.
Although Giuliani has not been accused of transgression, he remains vulnerable to federal scrutiny because Trump left office last month without granting pardon, despite months of speculation that Giuliani might receive preventive clemency.
Before Trump issued a wave of forgiveness on his last day in office, Giuliani said on his radio show that he needed no forgiveness. “I don’t commit crimes,” he said.
In the final weeks of the Trump administration, Giuliani discussed with his associates whether to ask for forgiveness before choosing not to, said two people with direct knowledge of the discussions.
The White House Council Office warned against Giuliani’s preemptive forgiveness, said one of the people, because that could raise questions about whether he needed clemency for his involvement in the January 6 rally, the focus of the current Trump trial meeting. impeachment. It is unclear whether federal prosecutors in Washington who investigate the riot are also examining Giuliani’s speech at the rally.
In Manhattan, the federal investigation into Giuliani came out of a case against two Soviet-born men, Lev Parnas and Igor Fruman, who helped on their mission in Ukraine.
Before even working for Trump, Giuliani already had business in Ukraine, including a 2017 contract to help the city of Kharkiv improve its emergency services and reinforce its image as an investment destination. The deal was settled by Pavel Fuks, a wealthy Ukrainian-Russian entrepreneur who said that Giuliani was hired to lobby the city, a statement that Giuliani denies.
Manhattan prosecutors examined Giuliani’s negotiations with Fuks, informed people said.
Manhattan prosecutors also interviewed at least one witness who testified before Congress during Trump’s impeachment process as part of an examination of Giuliani’s potential business in Ukraine and his role in pressuring the Trump administration to oust the American ambassador in Kiev.
While pressing Ukraine to investigate Trump’s political rivals, Giuliani was determined to remove the ambassador, whom he saw as an obstacle to these efforts. At the request of Giuliani and other Republicans, Trump ended up dismissing the ambassador, Marie L. Yovanovitch, a decision that was at the heart of the first impeachment trial.
Giuliani said he served as Trump’s attorney, but federal prosecutors in Manhattan investigated whether he also worked secretly for Ukrainian officials or oligarchs who wanted the ambassador to be removed for his own reasons, according to people familiar with the matter.
Under the Foreign Agent Registration Act, it is a federal crime to attempt to influence or lobby the United States government at the request or guidance of a foreign public official without disclosing it to the Department of Justice.
Yuriy Lutsenko, one of the officers who pressured Giuliani and his associates to fight for the removal of the ambassador, helped with the Ukrainian earth-digging mission. At the same time, Giuliani sought hundreds of thousands of dollars in deals with Lutsenko, a possible deal that has attracted scrutiny from prosecutors and the FBI. Giuliani said he declined the deal.
Maggie Haberman, Kenneth P. Vogel, Andrew Kramer, Maria Varenikova, Benjamin Weiser and Nicole Hong contributed to the report.