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.