High-profile nature of search highlights inquiry’s seriousness and suggests officials may have new Ukraine-related leads to follow Rudy Giuliani at the White House last year. Former prosecutors say the warrant’s details suggest some potential charges against Giuliani. Photograph: Chip Somodevilla/Getty Images The extraordinary FBI raid on Rudy Giuliani’s New York apartment and office has sparked debate about what criminal charges Giuliani may face, and signals a widening criminal investigation into his Ukraine drive to help Trump in 2020 by sullying Joe Biden, former prosecutors say. The high-profile nature of the raid meant it required senior Department of Justice signoff, and underscored the investigation’s seriousness and progress. It also obtained several of Giuliani’s electronic devices and thus may have harvested a rich trove of new evidence and leads for investigators to follow. “A search warrant involving a lawyer is always a sensitive matter, and even more so when the lawyer was the president’s lawyer,” said Mary McCord, a former prosecutor who led the national security division at the DoJ at the end of the Obama administration until May 2017. She added: “This would have needed approval at a very high level within the Department of Justice, which would not have been given absent very solid grounds. And department lawyers would have thought through legal issues like the expected assertions of privilege.” Ex-prosecutors and lawyers note that Giuliani seemed to rely heavily on several controversial Ukrainian officials, including a politician linked to Russian disinformation in his drive to dig up dirt on Joe Biden and his son Hunter, who had ties to a Ukraine energy firm, to boost Trump. They also point out Giuliani played a key part in ousting the US ambassador in Kiev, suggesting the probe could be looking at whether Giuliani broke multiple laws. Several outlets have reported that Giuliani is being investigated to determine if he broke the Foreign Agents Registration Act, requiring people who lobby the US government on behalf of foreign officials to disclose that to the justice department. The inquiry is reportedly focused on Giuliani’s role in Trump’s firing of ambassador Marie Yovanovitch in May 2019, a move that Giuliani and two close associates – indicted earlier on charges of campaign finance violations – pushed, and a central issue in Trump’s first impeachment. The criminal inquiry into Giuliani, an ex-New York mayor and former federal prosecutor, grows out of one that in 2019 charged Lev Parnas and Igor Fruman, two Soviet-born Giuliani associates who were heavily involved in his Ukraine projects, with illegal campaign donations from a foreign source. Parnas and Fruman are slated for trial in October. Among the 2019 charges against Parnas and Fruman were several alleged illegal donations, including a $325,000 check to a pro-Trump Super Pac. In 2020, a second indictment charged Parnas and another associate, David Correia, with running a sham company called Fraud Guarantee, which was aimed ostensibly at protecting investors against corporate fraud, but allegedly bilked its investors out of $2m, and paid $500,000 to Giuliani for legal and technical advice. Correia pleaded guilty late last year and has been sentenced to a year in jail. According to the 2020 indictment, a Long Island backer of Trump loaned the $500,000 to Fraud Guarantee for Giuliani’s services in 2018, the year that Giuliani began working as Trump’s personal lawyer. Reuters has reported that the search warrant authorizing the raid, which seized over 10 cellphones and computers, was seeking information about Giuliani’s communications with more than a dozen individuals, including ex-Ukrainian prosecutors and political figures, and trying to learn of contacts he had with US officials about Yovanovitch. Former prosecutors say the warrant’s details suggest some potential charges against Giuliani. Andrew Giuliani condemns the raid outside his father’s New York home last week. Photograph: Lev Radin/Pacific Press/Rex/Shutterstock “It’s a very aggressive tactic to seek an attorney search warrant,” said Michael Zeldin, a former federal prosecutor. “The warrant lists a who’s who of Ukrainian officials with whom Giuliani is believed to have been working in 2019-20. The fact that a judge issued the warrant despite the high bar for obtaining one, would seem to indicate that Giuliani is at least a subject of what appears to include violations of the Foreign Agents Registration Act (Fara).” Giuliani has denied lobbying for any foreign officials. In a post-raid statement, he said his “conduct as a lawyer and a citizen was absolutely legal and ethical” and Monday he told Fox News federal investigators are “trying to frame him”. Likewise, Giuliani attorney Robert Costello has called the raids “legal thuggery”, noting that Giuliani offered twice to answer prosecutors’ questions – except ones involving privileged talks with Trump – and was rebuffed. Costello, who did not return several calls seeking comment, has indicated that attorney-client privilege issues will figure in Giuliani’s defense. Despite Giuliani’s adamant denials, DoJ veterans say the search warrant underscores the inquiry’s progress and multiple directions. “The search warrant could be a microcosm leading to several potential charges, including violations of Fara,” said Paul Pelletier, a former acting chief of DoJ’s fraud section. “And following the money could open up a pandora’s box of possible charges against Giuliani and his associates.” Other recent FBI moves suggest the Giuliani probe may be wider than Fara issues. The FBI also seized electronic devices from the home of Victoria Toensing, a conservative DC lawyer and Giuliani ally, who with her lawyer husband Joe diGenova represented a wealthy Ukrainian oligarch Dmitry Firtash fighting extradition to the US for several years on complex charges he violated the Foreign Corrupt Practices Act which bars bribes to win business. Firtash, who had a $1m contract with the two Washington lawyers for a year, reportedly played a role through associates in assisting Giuliani’s Ukraine search for Biden dirt. Toensing has indicated she was informed she is not a target in the federal inquiry. Phil Halpern, a recently retired federal prosecutor who spent 36 years dealing with corruption and campaign finance cases, said Giuliani’s Ukraine political work “exposes him to a veritable potpourri of different federal offenses”. “His efforts to assist the Trump campaign directly – and through his indicted associates Lev Parnas and Igor Fruman – could be viewed as illegal campaign finance violations as they were never recorded in any campaign finance disclosures.” Further, the $500,000 payment Giuliani received from Parnas and Fruman “could be seen as part of a wider bribery or money-laundering conspiracy”. With complex legal battles looming, Giuliani has been getting advice from Alan Dershowitz, the Harvard law professor emeritus who helped represent Trump during his first impeachment, and recently has launched high-decibel media attacks on the raid.