Rudolph W. Giuliani, President Trump’s lawyer who has led the most extensive efforts to damage his client’s political rivals and undermine the election results, discussed with him as recently as last week the possibility of receiving a pre-emptive pardon before Mr. Trump leaves office, according to two people told of the discussion.
It was not clear who raised the topic. The men had also talked previously about a pardon for Mr. Giuliani, according to the people. Mr. Trump has not indicated what he will do, one of the people said.
Mr. Giuliani’s potential criminal exposure is unclear. He was under investigation as recently as this summer by federal prosecutors in Manhattan for his business dealings in Ukraine and his role in ousting the American ambassador there, a plot that was at the heart of the impeachment of Mr. Trump.
Mr. Giuliani did not respond to a message seeking comment, but after a version of this article was published online, he attacked it on Twitter and said it was false.
Christianné L. Allen, his spokeswoman, said Mr. Giuliani “cannot comment on any discussions that he has with his client.”
And Mr. Giuliani’s lawyer, Robert Costello, said, “He’s not concerned about this investigation because he didn’t do anything wrong, and that’s been our position from Day 1.”
A spokeswoman for Mr. Trump did not respond to an email seeking comment.
Such a broad pardon pre-empting any charge or conviction is highly unusual but does have precedent. In the most famous example, Gerald R. Ford pardoned Richard M. Nixon for all of his actions as president. George Washington pardoned plotters of the Whiskey Rebellion, shielding them from treason prosecutions. And Jimmy Carter pardoned thousands of American men who illegally avoided the draft for the Vietnam War.
Mr. Trump has wielded his clemency powers liberally in cases that resonate with him personally or for people who have a direct line to him through friends or family, while thousands of other cases await his review.
A pardon for Mr. Giuliani is certain to prompt accusations that Mr. Trump has used his pardon power to obstruct investigations and insulate himself and his allies. Andrew A. Weissmann, a top prosecutor for the special counsel Robert S. Mueller III, has said that Mr. Trump’s dangling of pardons for his allies impeded their work.
In July, Mr. Trump commuted the sentence of his longtime adviser Roger J. Stone Jr., who had refused to cooperate with the special counsel’s investigators and was eventually convicted of seven felonies. Last week, Mr. Trump pardoned his former national security adviser Michael T. Flynn, who had backed out of his cooperation agreement with the special counsel’s office for “any and all possible offenses” beyond the charge he had faced of lying to federal investigators.
The Flynn pardon raised expectations that Mr. Trump would bestow clemency on other associates — like his former campaign chairman Paul Manafort, who refused to discuss matters from the 2016 election with prosecutors — in his final weeks in office.
The president’s discussions of a pardon for Mr. Giuliani occurred as he has served as one of the loudest voices publicly pushing baseless claims of widespread election fraud that cost Mr. Trump the election. Many of Mr. Trump’s longtime aides have refused to do the president’s bidding on the election results, but Mr. Giuliani has repeatedly thrust himself into the spotlight to cast doubt on them, further ingratiating him with the president.
Mr. Giuliani has asked Mr. Trump’s campaign to pay him $20,000 a day for his work on trying to overturn the election, a figure that would make him among the most highly paid lawyers in the world. The staggering sum has stirred opposition among Mr. Trump’s aides that Mr. Giuliani has perpetuated the claims of election fraud in hopes of making as much money as possible.
Mr. Giuliani has expressed concern that any federal investigations of his conduct that appear to have been dormant under the Trump administration could be revived in a Biden administration, according to people who have spoken to him.
Legal experts say that if Mr. Trump wants to fully protect Mr. Giuliani from prosecution after he leaves office, the president would most likely have to detail what crimes he believed Mr. Giuliani had committed in the language of the pardon.
Federal prosecutors in Manhattan have been investigating since 2019 the role of Mr. Giuliani and two other associates in a wide-ranging pressure campaign directed at pushing the Ukrainian government to investigate Mr. Trump’s rivals, namely the son of Joseph R. Biden Jr.
The two Giuliani associates — Lev Parnas and Igor Fruman — were arrested in October 2019 as they prepared to board a flight from Washington to Frankfurt with one-way tickets. Mr. Parnas and Mr. Fruman were charged with violating campaign finance laws as part of a complex scheme to undermine the former American ambassador in Kyiv, Marie L. Yovanovitch, whom Mr. Giuliani and Mr. Trump believed should have been doing more to pressure the Ukrainians.
Prosecutors in Manhattan continued to investigate Mr. Giuliani’s role in the scheme over the past year, focusing on whether he was, in pushing to oust the American ambassador to Ukraine, essentially double dipping: working not only for Mr. Trump but also for Ukrainian officials who wanted the ambassador gone for their own reasons, according to people briefed on the matter.
It is a federal crime to try to influence the United States government at the request or direction of a foreign official without disclosing their involvement. Mr. Giuliani has said that he did nothing wrong and that he did not register as a foreign agent because he was acting on behalf of Mr. Trump, not any Ukrainians.
Even as Mr. Trump maintains that the election was stolen and files lawsuits aimed at delaying its certification, his White House is preparing for the final stages of his presidency. The end of any administration typically prompts a wave of pardons, particularly when a term has been engulfed in controversy like Mr. Trump’s, in which several people close to him became ensnared in federal investigations.
“The pardon power has been used by many presidents in politically self-serving ways, whether it was George H.W. Bush or Clinton,” said Jack L. Goldsmith, a professor at Harvard Law School, citing how Mr. Bush pardoned six of his associates — including the former Defense Secretary Caspar W. Weinberger — for their role in the Iran-contra affair.
“Politically, a pardon of Giuliani would be explosive,” Mr. Goldsmith added, “but pardoning pals has been done before.”
Under previous administrations, presidents have largely granted pardons after they have gone through a formal review process at the Justice Department, where lawyers examined the convictions, discussed the ramifications of the potential pardon with prosecutors and then provided the White House with recommendations on how to proceed. On several occasions, Mr. Trump has gone against the Justice Department’s recommendations and the advice of his own White House advisers, granting pardons to political allies and celebrities.
When presidents have deviated from that process, scandals have occasionally occurred, especially on pardons in the final days of the administration. On the final day of Bill Clinton’s presidency, he granted a pardon to Marc Rich, a wealthy financier and longtime Democratic donor who was considered a fugitive as he had fled the United States to avoid tax charges.
Prosecutors in Manhattan investigated whether the pardon had been part of a quid pro quo, but no one was ever charged. At the time, Mr. Giuliani, who had helped bring criminal charges against Mr. Rich years earlier as a federal prosecutor, was deeply critical of the move, calling it “a disgrace” and declaring it “a midnight pardon.”
No president has tried to grant someone a pardon for crimes they have not yet committed — essentially a prospective get-out-of-jail-free card — and legal experts say it is unlikely to hold any weight.
Ben Protess contributed reporting.
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