Rudy Giuliani speaks at the Iran Freedom Convention for Human Rights and democracy in Washington in May. Photo: Andrew Harnik/AP
As counsel to President Donald Trump, former New York City Mayor Rudolph Giuliani has made statements, ostensibly in his client’s defense, that have left some in the legal realm scratching their heads.
One critic, a retired federal appellate judge, even asked in a letter to the editor of the New York Law Journal why the former mayor and Manhattan U.S. attorney hasn’t been brought up on disciplinary charges.
As for New York attorneys who have worked closely with Giuliani and the offices he has led in the past, some recall his days as the hard-charging U.S. attorney for the Southern District of New York or the two-term mayor who took credit for making New York City safe and leading the city in the wake of the Sept. 11, 2001, terrorist attacks and wonder what’s become of him.
Others, however, say that, despite Giuliani’s marquee accomplishments, he might not have much to boast about in terms of his legal acumen.
Martin & Obermaier name attorney John Martin, who served as U.S. attorney for the Southern District of New York immediately before Giuliani became the head of the office in 1983, and later served as a district judge in the Southern District for 13 years, spoke of a dissonance between the Giuliani he’d known and the one he sees working for Trump today.
“Back in the day he and I had differences on some things but I always thought of him as a good lawyer,” Martin said of Giuliani. “I’m not so sure I think the same thing about him today.”
Giuliani himself did not respond to direct requests for comment. A number of past and recent allies of his likewise did not comment, either by not responding to requests sent by the New York Law Journal, or explicitly declining those requests.
Giuliani’s reputation for pugnacity extends back to his time as U.S. attorney, according to prosecutors who served in the office at the same time. According to one person, the trait cut both ways.
The attorney, who is now a partner at a top law firm and was granted anonymity to be able to speak freely about his time working under the future mayor, said in some ways Giuliani’s approach as U.S. attorney was a good thing. He was extremely aggressive, the litigator said, and gave line assistants a lot of leeway, while pushing them hard on their cases.
These same tactics earned Giuliani and the office criticism from judges and the public for at times stepping out of line, such as the use of public "perp walks," which predictably garnered media coverage for the SDNY and placed the accused in a harshly negative light, and accusations of leaks to the media.
“He was criticized and praised for just that—being very aggressive, not being shy about going after anybody,” the attorney said.
Now, the attorney joins Martin and others, some of whom declined to go on the record, in echoing various levels of bewilderment, frustration, and concern about the turn they've seen their old boss and colleague take in representing Trump. In some instances, the bond was even closer; the attorney said that Giuliani joined in some family functions.
“The new Rudy we don’t understand,” he said.
The attorney said two specific issues stood out for him and others he’d been in discussions with. First, there was disappointment at what the lawyer described as Giuliani “turning a blind eye” to what he believed were evident issues with Trump’s actions and behaviors. Similarly, former prosecutors were frustrated at Giuliani’s new-found concerns over law enforcement and prosecution tactics by Special Counsel Robert Mueller III and other federal prosecutors that are, by the attorney’s account, “tame compared to some of the shit Giuliani used to do.”
“This is like routine prosecution. There’s been no overreaching that any of us have seen in any of those offices,” the attorney said. “Mueller doesn't hold press conferences. Rudy would hold press conferences every week, beating his own drum and carrying on.”