Rudy Giuliani Could Be at the Ultimate Crossroads: To Protect Trump or Protect Himself 

Rudy Giuliani has faced almost every professional, personal and legal woe imaginable while connected to Donald Trump: multiple criminal investigations, mounting civil liabilities and likely disbarment. 

With so many sources of distress, it is little wonder why current and former Trump insiders and a number of legal experts think the former New York City mayor and ex-personal attorney to the president of the United States might want to be “queen for a day.”

In late June, Giuliani voluntarily sat down with Special Counsel Jack Smith’s office to answer questions, another in a series of interviews that federal prosecutors have conducted with the former president’s innermost circle as part of the Justice Department’s sweeping criminal probe into the chaotic and violent events surrounding the last White House election. 

Such proffer sessions typically last a day, usually with the benefit of an agreement immunizing the interviewee from any criminal liability for their answers — hence the royalty moniker that often brings witnesses to a decision point of playing ball with prosecutors or defending themselves on trial in court. 

But Giuliani didn’t simply sit with prosecutors for one day, a seemingly small distinction that has nonetheless raised eyebrows by raising the prospect that a man who was once hailed as “America’s Mayor” after the Sept. 11, 2001, terrorist attacks and more recently central to so many moments in the Trump era could be at the ultimate crossroads: To protect Trump or protect himself. 

Giuliani attorney Robert Costello confirmed in a phone interview that his client spoke with the special counsel’s office over the course of two consecutive mid-week mornings for about three to four hours each day.

Prosecutors wanted to discuss with Giuliani the events between Election Day 2020 and Inauguration Day 2021, Costello said. He attributed the separate sessions to DOJ accommodating his client due to mundane scheduling matters connecting to Giuliani needing to leave early in the afternoon to host a local New York radio show. 

"Nothing damaging was disclosed," Costello said. "Rudy Giuliani, when asked the question, tends, you know, he's asked a one-sentence question, and he answers in paragraphs. That's just the way he is. He gives complete and fulsome answers, and oftentimes volunteers information that he thinks is relevant that they didn't ask about, which takes a lot of time.”

‘Different Landscape’

Current and former Trump insiders who noticed the scheduling shake-up with Smith's investigators didn’t view it so blithely. 

“One day? You don’t know what to make of [it],” Trump’s former White House attorney Ty Cobb told The Messenger, noting it could be a mere courtesy or an attempt to negotiate for something else from federal prosecutors as they consider whether to bring federal charges against Trump tied to the 2020 election and Jan. 6, 2021, insurrection at the U.S. Capitol. 

“Two days though suggests that the DOJ may be considering his value as a witness,” Cobb added.

Former federal prosecutors and a defense attorney also viewed that outcome as a possibility. Mitchell Epner, who formerly served inside the U.S. District of New Jersey, called proffer sessions typically short and grueling affairs. In a reverse proffer, prosecutors may reveal evidence that they could deploy to convict a target if they do not plead guilty. 

“That is not standard operating procedure,” Epner said of the two-day questioning of Giuliani.

Ex-federal prosecutor Renato Mariotti noted that the Justice Department had no need to keep the septuagenarian on the hot seat for so long on ceremony — or to hurry him out the door.

“Giuliani touched a lot so they have a lot to ask about,” Mariotti told The Messenger.

Over the past two years, at least three criminal investigations into Giuliani’s activities have been publicly known: two tied to efforts to overturn Trump’s defeat and one seemingly linked to the former president’s first impeachment. In 2021, the FBI conducted a court-authorized search of his home and office in connection with an investigation into his lobbying in Ukraine. Federal prosecutors from the Southern District of New York, a jurisdiction he once led as a U.S. attorney, disclosed last November that charges against Giuliani are not “forthcoming” in that investigation — but court papers filed earlier this month suggest that authorities still have electronic devices from that raid.

Against this backdrop, Giuliani’s back-to-back sessions last month with the special counsel’s office may make Trump’s inner circle raise an eyebrow — and by one account, already has. 

A source familiar with the Trump team's thinking told The Messenger they know a good lawyer like Bob Costello doesn’t send Giuliani in for one day, let alone two, without getting something in return from the Justice Department. They're asking themselves — and they're not sure the answer — whether Giuliani shared incriminating material.

“I’m sure the pressure is immense,” the source said, adding when asked if Giuliani could end up on the MAGA outs if he becomes a Smith witness: “At this point in Rudy’s age and career, does that matter?”

Attorney Joseph Bondy, who represented Giuliani’s ex-associate Lev Parnas in a criminal case associated with Trump’s Ukraine scandal, noted that the former mayor now finds himself in a “different landscape” than when the 45th president of the United States was first impeached in late 2019 for abuse of power and obstruction of Congress connected to his lawyer’s overseas bid to entice another country’s government into investigating the Biden family.

“He is older and more fragile, no longer protected by the Trump cabal, and involved in multiple criminal investigations that, if brought, could each result in his potential conviction and imprisonment,” Bondy told The Messenger. “Of course, Rudy understands this. The question is really, will he fall on the sword and protect the former president — who, it currently appears, could care less about him — or attempt to cooperate with the special prosecutor and mitigate the potential for conviction and a prison sentence at the age of 79?”

For his part, Costello insists that Trump has nothing to worry about from Giuliani's conversations with the special counsel — and anyone suggesting as much is mistaken.

"I can tell you point blank, outright, without fear of retribution or correction, there was no quid pro quo," Costello told The Messenger. "We didn't get anything in return. We were telling the truth and we had nothing to hide because Rudy Giuliani didn't do anything wrong. It’s that simple."

"There is nothing for Donald Trump or anybody associated with Donald Trump to worry about," he added, "because we didn't implicate anybody in anything."

Asked if Giuliani would accept a cooperation agreement in exchange for DOJ not pursuing criminal charges against his client, Costello replied, "I'm not gonna answer their speculative question like that. They're not going to charge him."

Giuliani could not be reached for comment, and Smith’s DOJ spokesman Peter Carr declined to comment.

‘This Is Not a Fraud Case’’

Giuliani has been shouldering another host of burdens in the wake of his efforts to overturn the 2020 election results. 

On election night, a visibly inebriated Giuliani was the only Trump advisor to support the former president’s plan to declare victory, according to the House Select Committee that investigated  the Jan. 6 insurrection — an event that led to five deaths and Trump’s second impeachment. The former mayor’s efforts to overturn Trump’s defeat only grew more visible, and less dignified, from there. 

Sharing a stage with fellow Trump-aligned lawyer Sidney Powell, Giuliani appeared to have hair dye dripping down his face as the legal team unveiled a map announcing “MULTIPLE PATHWAYS TO VICTORY.” States where Trump and his allies planned to contest the results were highlighted in red, and Giuliani focused on a federal court in Pennsylvania, where then-President-elect Joe Biden won by 80,555 votes.

The contrast between Giuliani’s public rhetoric and courtroom argument was stark. At that press conference, and one in front of Four Seasons Landscaping in Philadelphia, Giuliani alleged massive voter fraud. Once in court, Giuliani told a federal judge: “This is not a fraud case,” focusing instead on supposed procedural irregularities. In one memorable gaffe, Giuliani told a federal judge to apply “normal scrutiny” to the case — a standard of review that doesn't exist. 

Skewered in the press and among his professional colleagues, Giuliani lost his lawsuit in blistering rulings in the lower court and on appeal. A three-member panel of the D.C. Bar’s Board of Professional Responsibility found Giuliani’s courtroom antics “frivolous” enough to recommend his disbarment, and a federal judge recently took time out of sentencing a convicted Jan. 6th rioter in an unrelated case to marvel at how flimsy Giuliani’s arguments were.

"I was so dumbfounded that the lawyer representing the president would make such a poor presentation,” remarked U.S. District Judge Royce Lamberth, a Ronald Reagan appointee who said he knew Giuliani "in my previous life” as a former top Justice Department official.

But Giuliani's multi-pronged role in Trump's efforts to stay in office went far beyond litigation. 

He memorably went to several 2020 battleground state capitals across the country to claim what he refused to allege in court: widespread voter fraud. Those efforts also failed, with state and local authorities certifying the election results in every forum the specious claims of fraud were aired.

Giuliani’s attacks on Biden’s victory, however, did not end there. The former mayor participated in the scheme to send fake Trump electors in states where Biden won, and he stood on a stage at the Ellipse outside the White House on Jan. 6, 2021, exhorting a crowd of restive supporters of the former president to engage in “trial by combat.” 

Now, Giuliani’s variegated attempts to keep Trump in office are up for a reckoning in at least two active criminal investigations by Smith and Fulton County District Attorney Fani Willis, a Democratic-elected official who has refused to rule him out as a target of her investigation in Georgia. 

‘My Rudy’

The ongoing criminal investigations also will test how Trump rewards the steady loyalty of a man he nicknamed “My Rudy,” who lent a New York City developer and reality TV star the gravitas that came with support from “America’s Mayor.” His steady hand in the wake of Sept. 11 made Giuliani Time’s “Man of the Year,” and he parlayed his acclaim into an unsuccessful Republican presidential run in 2008. 

By the time the Trump train veered toward the White House, Giuliani’s mayoral gloss already had lost some of its sheen. His off-the-cuff 2015 comment that President Barack Obama didn’t “love America” got widely lampooned and ultimately inspired Obama to swing back during remarks commemorating the 50th anniversary of ‘Bloody Sunday’ and the civil rights march from Selma to Montgomery, Alabama.

In 2017, Biden jeered that Giuliani formed every sentence with “a noun, a verb and 9/11,” but Giuliani still startled some observers by how he spent reputational currency on Trump. 

In one instance, Giuliani represented Turkish-Iranian gold trader Reza Zarrab in a case that embarrassed Turkey’s strongman leader Recep Tayyip Erdogan, a Trump ally. Giuliani shuttled between the U.S. and Turkish capitals trying to broker a prisoner swap to free Zarrab, who was accused of funneling billions of dollars from Iran, with the help of friendly Turkish officials and institutions.

A federal judge told a reporter that the move seemed to encapsulate the “new Rudy,” seemingly out of step with the anti-Iran hawk he knew. His then-firm, Greenberg Traurig, appeared to be a registered agent for the Turkish government, prosecutors were quick to note. 

Before his term as mayor, Giuliani served in the Reagan administration as U.S. Attorney for the Southern District of New York, launching high-profile racketeering cases that loosened organized crime’s grip on the city. Decades later, the same prosecutorial office’s investigation of him came as a personal shock. In one interview, Giuliani called his SDNY investigators “a**holes."

Trump relied upon Giuliani’s then-solid legal pedigree long before the 2020 election, including during Special Counsel Robert Mueller’s investigation into Russian interference in the 2016 election. Giuliani had a unique qualification for handling that probe: There’s a photograph of him shaking the hand of Mueller, who was an FBI director when he visited the fallen World Trade Center site in 2001.

That image of Giuliani stands as a testament to long bygone days. He’s been at the tip of the MAGA spear for several years now, and like his longtime friend and former client Trump blames persecution for his potential criminal exposure. Now Giuliani’s law license may be on borrowed time. He also faces multiple civil lawsuits in connection with the 2020 election — and another accusing him of sexual assault. 

At a time when he needs Trump’s help more than ever, those who know Giuliani describe him as an outcast. 

“The business of politics is not known for loyalty,” Hank Sheinkopf, a longtime Democratic consultant in New York who has worked with Trump, told The Messenger. “It is known for character assassinations and gossip and competition. Right now, Rudy Giuliani is a carcass that political people are feasting on and for anyone he ever hurt in the course of his business there’s joy, not pity, for what he’s experiencing.”

While Trump may have sworn off his hometown in favor of South Florida, Giuliani remains a New Yorker, one whose fortune is intricately bound to the city’s other native son.

“Trump is a curse word in NYC, and Rudy’s association with Trump makes him part of the curse word,” Sheinkopf said. “It’s not even detestation. It’s hatred. He’ll suffer for it. His fellow New Yorkers will never forgive him.”

Costello dismissed any speculation or commentary that his client is being shunned from the ex-president's orbit. "That's bulls**t," he said. "And I know that for a fact. That's just nonsense."

"Do you know what it's like when you have somebody in Trump's position and you have, what I refer to as the palace guard? All of these people around," the Giuliani attorney added. "I mean, there's always naysayers in any group. There are people out there with their own agenda and this is no different."

A Trump spokesman didn’t respond to an email requesting comment.

For Cobb, the former Trump White House lawyer whose tenure overlapped briefly with Giuliani’s arrival as a personal attorney to the president during the Mueller probe, Giuliani’s travails point to a larger, national truism.

“There is no country that cannibalizes its heroes the way America does,” Cobb told The Messenger. “The higher you are, the farther you fall.”