What Rudy Giuliani Is Really Up To

Rudy Giuliani looking at his clasped hands.
Jacqueline Larma / AP

Updated on December 1, 2020, at 5:32 p.m. ET.

In his frenzied crusade to help President Donald Trump overturn the 2020 election result, Rudy Giuliani has displayed many of the characteristics that Trump has long demanded in his personal lawyers—albeit with more surreal and comedic elements.

Giuliani has shown unswerving loyalty, gleefully obfuscated facts, launched wild attacks on the media, hosted circus-style press conferences, and gone to court, all in a fruitless, evidence-free quest to persuade several states to block Joe Biden’s electoral victories.

But that might not be Giuliani’s only—or ultimate—goal.

The former New York mayor might just be trying to save himself, according to the Department of Justice veterans and legal experts I spoke with. Giuliani seems to be facing growing legal threats, and he may be angling for a presidential pardon, they told me in interviews over the past few weeks.

According to a new report in The New York Times, Giuliani has had more than one discussion with Trump about getting a preemptive pardon, but whether Trump has agreed is unclear. (Giuliani’s personal lawyer denied to me last week that his client wants to secure a pardon from Trump, saying Giuliani hadn’t done anything wrong; on Twitter today, Giuliani himself denied the Times story.)   

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Giuliani faces potential criminal exposure stemming from his lengthy campaign to dig up dirt on the Biden family in Ukraine. Lev Parnas and Igor Fruman, the two Soviet-born men who worked closely with Giuliani in a widely debunked drive to link Biden and his son Hunter to corruption in that country, have been charged with making illegal campaign contributions. The pair were slated to go to trial in March, but that’s since been postponed to later in 2021. (Both Parnas and Fruman pleaded not guilty.) The FBI is also reportedly investigating Giuliani’s Ukraine efforts, including his possible ties to Russian intelligence. A key Giuliani contact in Ukraine for anti-Biden materials was Andrii Derkach, a lawmaker whom the Treasury Department sanctioned in September as an “active Russian agent” attempting to interfere in November’s election.

Giuliani’s zealous, bumbling efforts to help Trump make sense if he’s spooked and wishes to save his own skin. “After the Biden administration takes office in January, I would expect the DOJ and [the Southern District of New York] to sharpen their focus on financial crime, corruption, and money laundering,” Paul Pelletier, who served as the acting chief of the DOJ’s fraud division under Presidents George W. Bush and Barack Obama, told me. “With his foreign entanglements” and “business relationships with charged fraudsters … Rudy Giuliani’s conduct would surely invite specialized scrutiny. The greater the threat of prosecution, the more a presidential pardon would be welcome.”

Other ex-prosecutors I spoke with concurred. “It would make sense for Giuliani to look to his boss for a pardon that could immunize him from possible federal indictment on campaign finance, obstruction of justice, federal tax, and other related charges,” Phillip Halpern, a recently retired federal prosecutor who spent 36 years focused on corruption and campaign-finance cases, told me.

Prosecutors in the Southern District of New York, the office Giuliani once ran, which is known for its independence and handles many of the Justice Department’s highest-profile prosecutions, have reportedly been scrutinizing Giuliani’s links to Parnas and Fruman since last fall. Investigators have examined Giuliani’s financial dealings with the pair in part to discern whether Giuliani’s Ukraine work violated lobbying laws that require foreign agents to register with the United States government, according to the Times.

Prosecutors have charged Parnas and Fruman with scheming with foreign donors to funnel hundreds of thousands of dollars in illegal donations to one U.S. government official and political-action committees, including a pro-Trump super PAC.

With their trial coming up, Parnas and Fruman are likely to face mounting pressure to cooperate with prosecutors in an attempt to cut their potential punishment, ex-DOJ lawyers told me. In September, Parnas and Fruman were charged in a superseding indictment with additional campaign-finance crimes. SDNY prosecutors also added wire-fraud violations to their raft of charges against Parnas. A Florida-based firm called Fraud Guarantee, which was run in part by Parnas and which prosecutors’ complaint charges was a scam, is alleged to have bilked investors out of more than $2 million. (The degree of Fruman’s involvement in Fraud Guarantee is unclear.)

Parnas and another partner, David Correia, used the funds they raised for personal expenses, including “hundreds of thousands of dollars in rent for Parnas’s personal residence” and political donations, according to an SDNY press release. (Correia pleaded guilty to two of the five charges against him.)

Giuliani has a direct link to Fraud Guarantee, which, according to its website, pitched potential clients on its ability to help them “reduce and mitigate fraud.” According to Giuliani, Fraud Guarantee hired him, in part, to offer legal counsel on regulatory matters. Additionally, a consulting firm Giuliani runs was paid $500,000 by a Long Island lawyer as part of an alleged agreement to invest in Fraud Guarantee.

Justice Department veterans say that the risks for Giuliani have grown with the added charges against Parnas and Fruman, as either one could feel additional pressure to cut a deal. “More charges generally mean more incentive to cooperate,” Joshua Geltzer, a senior lawyer in the Justice Department’s national-security unit under Obama, told me. “And more charges that relate to Rudy, in particular, may well mean more incentive to cooperate about his actions.”

Other warning signs of potential legal trouble for Giuliani involve his dealings with Derkach, the Ukrainian lawmaker and alleged Russia agent. Giuliani met with Derkach more than once. In an October story, The Washington Post revealed that the White House was warned in 2019 that Giuliani was the target of an influence operation by Russian intelligence. It identified two meetings between the men: in Kiev in December 2019 and again in New York two months later, when the lawyer hosted Derkach on his podcast. At the Kiev meeting, they filmed a segment together for the ultraconservative One America News Network, in which they promoted widely discredited allegations about Biden.

Giuliani has touted Derkach’s unverified claims about the Bidens as “very helpful.” (In an apparent belated attempt to downplay his earlier praise for Derkach, Giuliani told the Post he was never informed that Derkach was a Russian intelligence agent, and that the Ukrainian lawmaker had only “secondary information” and Giuliani did not consider him a “witness.”)

These legal threats may well have been on Giuliani’s mind as he has worked feverishly and clumsily to keep Trump’s challenges to the election barely alive after multiple courts rejected them.

“Rudy’s doing everything he can not just to help Trump undermine Biden’s election, but in anticipation that POTUS will save Rudy from further investigation and legal trouble with a possible pardon,” said a former senior intelligence official in the Trump administration, who, like another source, talked with me on the condition of anonymity in order to speak candidly.

“No one has been more loyal to Trump than Rudy, so he’s probably at the top of Trump’s pardon list,” a veteran GOP operative in Washington added.

Robert J. Costello, Giuliani’s attorney and a former top prosecutor at SDNY, scoffed at the idea of Trump issuing his client a pardon. “He hasn’t done anything to merit a pardon,” Costello told me last week. “You have to have done something wrong to need a pardon.” Costello said that neither he nor Giuliani has been contacted by SDNY investigators about his dealings with Parnas and Fruman, or heard from the FBI about his work in Ukraine and possible ties to Russian intelligence there. Costello added that they have “no concerns” about the upcoming trial of Parnas and Fruman.

Still, Trump is said to be enthusiastic about using his sweeping pardon powers, and expectations have grown that some allies he portrays as victims of politically driven “deep state” prosecutions and probes will receive pardons. Before Thanksgiving, he pardoned one such victim, his ex–National Security Adviser Michael Flynn, who had twice pleaded guilty to lying to the FBI about his contacts with the Russian ambassador prior to Trump’s inauguration. (He later attempted to withdraw his guilty plea.) Other potential pardon targets include Trump’s longtime confidant Roger Stone and the former Trump-campaign chairman Paul Manafort, both of whom were charged and convicted as part of the Russia investigation. (The president has already commuted Stone’s sentence.)

The president also has the power to preemptively pardon individuals, which is what he’d do for Giuliani. “The president’s pardon power is extremely broad,” Donald Ayer, a former deputy attorney general in the George H. W. Bush administration, told me. “He can pardon anyone, and he can pardon them for crimes that have not been charged. Look at what President Ford did in the case of Richard Nixon.” (The White House did not respond to multiple requests for comment.)

However, Giuliani’s prospects could be undercut, ironically, by his erratic drive to overturn the election results.

Trump and a number of his advisers were reportedly irked by Giuliani’s Inspector Clouseau–like performance and the far-reaching voter-fraud conspiracies he—and the lawyer Sidney Powell even more so—pushed during a November 19 press conference at the Republican National Committee headquarters; Powell was ultimately ousted days after the RNC event.

What’s more, the image-obsessed Trump had something new to fret over when Stephen Colbert, Jimmy Kimmel, and other commentators had a field day ribbing Giuliani for his personal appearance at the press conference, where he sweated profusely with what seemed to be black hair dye running down his cheeks.

Giuliani’s “assignment is to speak in public and muck things up and to egg on the conspiracy hunters and members of the cult of Trump,” Stephen Gillers, an NYU law professor who says he went to law school with Giuliani, told me. “His job is to influence, or, more accurately, to distort public opinion.”

But in Trump’s eyes, Giuliani’s indefatigable efforts, against all odds and facts, to undermine Biden’s clear victory may count more than any lousy reviews his lawyer has received.

Which may explain why, the day after Pennsylvania finally certified Biden’s win, Trump phoned in to join a “hearing” on election-fraud allegations that GOP lawmakers and Giuliani hosted in a Gettysburg hotel ballroom. During the call—notwithstanding one district judge who days before rebuked Giuliani for a court filing he likened to “Frankenstein’s Monster”—Trump effusively praised his top lawyer for spearheading the challenges to the election results in Pennsylvania. “This is going to be your crowning achievement because you’re saving our country,” Trump said. It’s just this kind of reassurance that Giuliani may be banking on.