Rudy Giuliani's former colleagues reflect on his path from law-and-order champion to RICO defendant: "A tragedy"

Waving his glasses in front of his face while recording his YouTube show on Tuesday, Rudy Giuliani taunted the prosecutor who had just charged him with racketeering.

"You're screwed, Fani. Giuliani got new glasses. Ha! And he's like five times the lawyer … five times the lawyer you are? How can you? No. Well, you can't multiply by zero," Giuliani said.

Giuliani was one of 19 people, including former President Donald Trump, indicted in Georgia Monday in a broad racketeering case focused on their efforts to overturn the state's 2020 presidential election results. On his YouTube show Tuesday, he echoed the irony many of his former colleagues recalled in interviews in recent days, having watched Giuliani transform from a hard-charging federal prosecutor-turned-mayor — known for his tough-on-crime braggadocio — to defendant in a case painting him as a central figure in a "criminal enterprise" bent on overthrowing a president-elect. 

"What the hell do you know about racketeering? I know about racketeering," Giuliani said during his YouTube show, claiming, "I probably have done more against organized crime than any prosecutor in history."

Giuliani's sense that he was an original champion of racketeering, or RICO, prosecutions was echoed by Paul Shechtman, who in the early 1980s was chief of appeals under Giuliani, then the U.S. attorney for the U.S. Southern District of New York. At the time, Giuliani was becoming a household name in New York, known for pursuing mobsters and corrupt politicians. 

"In the 1980s, if you said that Rudy Giuliani had been indicted on RICO charges, someone would've thought it was a bad 'Saturday Night Live' skit," said Shechtman, who is now deputy commissioner of legal matters/general counsel for New York City's Department of Correction.

Columbia Law School professor Daniel Richman was a young federal prosecutor at the time working for Giuliani — in his own words, "a starry-eyed young assistant who thought Rudy was an inspiring leader and a prosecutor with a real moral compass and commitment to getting the law right."

Among Giuliani's major cases was the prosecution and racketeering conviction of Stanley Friedman, a former New York City deputy mayor and Bronx Democratic party boss. Before Giuliani prosecuted him, Friedman was a lawyer whose most famous client was local businessman Donald Trump; the firm Friedman worked for was founded by Trump's mentor, Roy Cohn.

"If you had told me that Rudy would be doing dirty work for Roy Cohn's protégé, I wouldn't have been able to fathom it," Richman said, "since I was involved in cases where Roy Cohn was deeply connected to mob figures."

Giuliani left the U.S. Attorney's Office in 1989 and four years later successfully ran for mayor, riding a "law and order" message to City Hall.

Giuliani's campaign rhetoric was brash and confrontational. During one September 1992 speech, he addressed hundreds of police officers who gathered near the Brooklyn Bridge to protest a civilian oversight board and other police reform efforts. Soon after, the police group rioted, shutting down the bridge, stopping traffic, shouting racial epithets and stomping on cars.

In the aftermath, some — including then-Mayor David Dinkins — criticized Giuliani for egging the police on, an allegation Giuliani called "dead wrong."

Giuliani was elected two months later, and reelected four years after that. He'd claim credit for a marked decrease in crime rates during his tenure, which ended a few months after the day that for years defined his legacy: Sept. 11, 2001.

"He was 'America's Mayor,' who led us through one of the most difficult periods in the history of the country," said Lou Ellen Barkan, who worked with Giuliani for four years as chief of staff to Deputy Mayor Randy Mastro.

After the attack on the World Trade Center, "people were pretty hysterical. And his behavior was so calming and reassuring, that even though we were all just beside ourselves, having him as the leader at that time was really great," Barkan reflected.

In the two decades since, Giuliani went into business for himself, ran for president and worked for a major law firm before serving as personal attorney to Trump, the role that ultimately led to his indictment. 

Giuliani faces 13 counts related to his alleged efforts to help Trump overturn the 2020 presidential election. By his own account, he spearheaded a campaign to challenge the results after Trump lost. He was central to internal planning and strategy, but also the most visible face of the Trump legal team — holding a famous press conference after the election at Four Seasons Total Landscaping in Philadelphia, saying Trump would not concede, and spreading misinformation in appearances before state legislatures.

The Georgia indictment alleges that Giuliani, "in furtherance of the conspiracy" to overturn the election, sought to push legislators in Arizona, Pennsylvania, Georgia and Michigan to "unlawfully appoint" presidential electors from their states.

He has not yet entered a plea in the case, but has denied wrongdoing.

One person who worked closely for years with then-Mayor Giuliani, but asked not to be identified, described his current situation as "tragic."

"It's hard, when you've worked closely with someone. Admired them, loved them. My time with him was the best job I've ever had," the person said. 

Asked about the comments by Giuliani's former colleagues, a spokesperson and political advisor for Giuliani brought up allegations about Democrats and "the Russian collusion hoax," a 2020 comment by then-candidate Joe Biden calling Giuliani "a Russian pawn," and "big tech" censorship of Hunter Biden's laptop.

"I would remind these 'former colleagues' that Rudy Giuliani is the most effective federal prosecutor in American history, he improved the quality of life for more people than any Mayor in American history, and he comforted the nation following September 11th," said the political advisor, Ted Goodman. "No one can take away his great accomplishments and contributions to the country."

Barkan struggles to explain a change in Giuliani's demeanor over the years that she also calls "tragic."

"Rudy Giuliani is a tragedy of biblical, Shakespearean proportions. I think a hundred years from now, somebody will write an opera about this guy's life," Barkan said.

"He achieved remarkable things with a group of remarkable people, and to see where he is today, for those of us who knew him at that time, is to recognize that he's no longer the same person," Barkan said. "That trajectory has been, in the classical sense of the word, really a tragedy, for him, of course, and for all the people who knew and loved him."

But how did the guy who went after Donald Trump's lawyer, and others close to his mentor, turn into the guy risking prison for Trump? 

Barkan says she frequently thinks about "how did we get so far down this road?"

"Politics brings people together who have a mutual agenda, whether it's personal or professional. The combination is like putting two chemicals in a jar where you don't really know what the response is going to be — like in a chem lab in high school," Barkan said. 

"And the teacher might say, 'don't put that in there, you'll have an explosion.'"

In:
• Rudy Giuliani
• Donald Trump

Graham Kates

Graham Kates is an investigative reporter covering criminal justice, privacy issues and information security for CBS News Digital. Contact Graham at KatesG@cbsnews.com or grahamkates@protonmail.com