Rudy Giuliani's SDNY saga: from top prosecutor to subject of scrutiny

Prosecutors brought a criminal case against their own colleague, a well-regarded prosecutor who was charged with stealing more than $41,000 in cash and five pounds of drugs from the office evidence locker.

The US Attorney who brought the case? Rudy Giuliani.

Thirty-five years later, Giuliani is now under investigation for a wide range of possible crimes by the very office he led from 1983 to 1989, a scenario that has prompted intense public interest and media attention and has led Giuliani to lash out against those investigating him, in one instance referring to the prosecutors as "assholes."

But current and former members of the office known as the US Attorney's office for the Southern District of New York, or SDNY, have been disappointed and dismayed to witness the predicament of their former leader, even as they believe the office should pursue any potential wrongdoing.

The SDNY community has watched in disbelief as Giuliani continues to seek the spotlight even as the investigation has unfolded and expanded into new fronts on a nearly weekly basis. The impeachment inquiry has also unleashed new evidence regarding his role performing shadow diplomacy on behalf of President Donald Trump as recently as Tuesday.

New documents disclosed by House Democrats showed Giuliani wrote a letter with Trump's "knowledge and consent" to Volodymyr Zelensky, Ukraine's president-elect, seeking a meeting last spring.

"He was like all of us. He's imperfect, but he was a very good and inspiring United States Attorney who made major prosecutions," said Paul Shechtman, a partner at law firm Bracewell LLP who worked under Giuliani as a federal prosecutor, including as head of the office's appeals division.

"For those of us who worked for him, the fact that our old office is investigating him is a dark day," Shechtman said.

It's a sentiment shared by the younger generation of alumni, many of whom point to their years in the office as the highlights of their career.

"It's one thing to be investigated. Innocent people get investigated," said Glenn Kopp, a former assistant US attorney in Manhattan from 2008 through 2013. If Giuliani is indicted, Kopp said, "it will be a sad day. I can speak for myself, and I would not be happy with that result."

But Kopp added he has confidence that the office would bring a case only if warranted by the evidence. "SDNY will make a well-reasoned, thoughtful, and well-investigated determination of whether to pursue a case against Rudy," he said. "I think they will do it smartly and thoughtfully and carefully and they won't rush to judgment."

In October, prosecutors charged two of Giuliani's associates, Lev Parnas and Igor Fruman, with campaign-finance crimes, and since then investigators have expanded their inquiry to include Giuliani. Authorities are examining his business dealings with the Soviet-born men in Ukraine, and FBI agents and prosecutors have questioned witnesses about their potential or actual business arrangements with Giuliani, his work on the ground in Ukraine and the identities of his clients, CNN has reported.

Giuliani has denied wrongdoing. In a text message to CNN he suggested SDNY has behaved improperly.

"If they are investigating me they are acting irresponsibly and allowing massive leaking of things I didn't do to harm my reputation," he wrote, noting that prosecutors haven't requested any documents or other material from him. "I learn what I know from press and that is one false charge after another."

"I'm sorry any of my former colleagues are disappointed," he added, "I'd just have to say is all we know are leaks and they should give me the benefit of the doubt on those."

Giuliani took a personal interest in some cases

His position as the subject of scrutiny is a dramatic turn from his time atop perhaps the most powerful prosecutors' office outside of Washington. As Manhattan US Attorney, Giuliani, who was appointed to the post by President Ronald Reagan after having worked as a lower-level prosecutor in the office and the number three lawyer at the Department of Justice, was known as a charismatic leader, using both the bully pulpit and the courtroom to win high-profile victories that burnished the office's reputation.

He is credited with mobilizing prosecutions against the five heads of the New York crime families, a feat that, to some, seemed impossible. He also attracted attention to white-collar crime cases, not without controversy, by ordering "perp walks" of Wall Street executives being led in handcuffs from their bustling trading floors.

Giuliani took a personal interest in some cases. He was the lead prosecutor in the high-profile public corruption trial of Stanley Friedman, the chairman of the Bronx Democratic Party who was charged with racketeering and bribery involving the city's Parking Violations Bureau. Giuliani cross-examined Friedman, who testified in his own defense. Friedman and two others were convicted on all counts.

In the years after he left the office, Giuliani departed from the traditional path of doing defense work, becoming mayor of New York City and then rising to a national political figure in the aftermath of the terrorist attacks of September 11, 2001.

Though he didn't maintain strong ties with his former office, he wasn't always estranged from it, as he is today. As recently as November 2014, he was welcomed back as a guest speaker in its lecture series for prosecutors, which has featured high-profile guests including Supreme Court Justices Elena Kagan and Stephen Breyer, former US Attorney Mary Jo White and former FBI Director Robert Mueller.

And Giuliani has some professional ties to the current senior members of the office. US Attorney Geoffrey Berman and Giuliani were partners at law firm Greenberg Traurig, but a person familiar with the matter has told CNN they did not work on any cases together. Craig Stewart, chief counsel to Berman, was a young assistant US attorney when Giuliani led the office.

A spokesman for the US attorney's office declined to comment.

But more recently, particularly amid Giuliani's work as President Donald Trump's personal attorney, New York federal prosecutor alumni have bristled at his behavior and his comments, particularly his criticism of the office's actions in cases such as the prosecution of Michael Cohen, a former personal attorney to the president.

"I think the biggest constant from the Southern District community has been, can you believe that Rudy Giuliani was ever US attorney? What an embarrassment," said Alvin Bragg, a former prosecutor in the office who is running for Manhattan district attorney as a Democrat. "I've heard that from several people. How repugnant and foolish his conduct has been."

Referencing Giuliani's appearance at the office's lecture series, he added: "If he's getting invited back now to speak, it's going to be with a lawyer by his side."

For Giuliani's part, he has criticized his former office's handling of the investigation of him, saying in a December interview in New York Magazine that, "If they're investigating me, they're assholes. They're absolutely assholes if they're investigating me."

But he is one of the few people personally familiar with the particular sensitivities that accompany an investigation of someone with ties to the office.

Public figure with 'his own baggage'

In the 1985 case, Giuliani oversaw a swift investigation of his then-employee, Daniel Perlmutter, an assistant US Attorney who later pleaded guilty to drug possession and stealing government property.

Perlmutter, then 29, had abruptly stopped showing up to work, leading members of the office to believe he was sick, and prompting Giuliani to personally deliver food to his home, recalled Benito Romano, who was then executive assistant US attorney under Giuliani and who later himself became US Attorney. Perlmutter didn't respond to an email sent to an address associated with him.

Perlmutter, however, in fact was deep in the midst of a drug binge, Romano said, and when Giuliani and the office later realized what Perlmutter had done, Giuliani initially sought to prosecute the case himself, representing the office in Perlmutter's initial court appearance, according to media accounts.

Giuliani later conceded that prosecutors from the Department of Justice should take the lead going forward, to avoid a conflict of interest.

"He felt very strongly that the Southern District could manage this on his own, but he came around, and I think he understood why it was important," Romano said. "On the whole, looking back on it, I think Rudy handled it extremely well."

Romano said he hasn't spoken to Giuliani in several years. Regarding SDNY's investigation of his former boss, he said, "the office is doing what it has to do."

"I doubt seriously whether Rudy is considered one of its own" at this point, he said. "It's been a long time, and he's been a public figure in his own right, with his own baggage."