It’s nearly unheard of for a federal prosecutors’ office to investigate one of its own, but in 1985, the Manhattan US Attorney’s office did just that.
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.