Rudy Giuliani discusses his time working with James Comey, says 'he was like a choir boy who turned into a devil'

• Former FBI Director James Comey and President Donald Trump's outside attorney, Rudy Giuliani, have been at each other's throats in recent weeks.
• That level of animosity between the two is relatively new, as they once had great admiration for each other.
• Giuliani was Comey's boss in the late 1980s.
• Giuliani told Business Insider in an interview that he knows Comey "very well" and that he hired him.
• "He was like a choir boy who turned into a devil," Giuliani said.

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James Comey and Rudy Giuliani aren't bit fans of each other.

But it wasn't always like that.

Before Giuliani, now President Donald Trump's outside attorney, was calling the former FBI director "Judas" and Comey was discussing the "resentment" for Giuliani that existed in the US Attorney's Office for the Southern District of New York when Comey took over as US attorney in 2002, Giuliani was Comey's boss.

And there was mutual admiration.

"Comey? Of course I know Comey," Giuliani said in an interview with Business Insider. "I know Comey very well. I hired him."

Giuliani hired Comey in 1987 to work as an assistant US attorney in the Southern District of New York. At the time, Giuliani was the US attorney. They worked together from Comey's hiring until Giuliani departed the office in 1989.

"I remember his work in the office," Giuliani said of Comey. "I met with him a few times when he was in the Justice Department, when he was FBI director. I had a high regard for Comey until he pulled the Clinton thing in July of 2016. And strangely, even though it condemned Hillary ... I thought it was one of the most unethical things I've ever seen."

The "Clinton thing" refers to Comey's decision to make a public announcement - somewhat unprecedented for an FBI director - exonerating 2016 Democratic presidential nominee Hillary Clinton for the scandal surrounding her use of a private email server while she was secretary of state.

Comey would, just prior to the election, reopen that investigation upon the discovery of additional emails on disgraced Democratic Rep. Anthony Weiner's laptop, but none of the emails proved to be incriminating, and the FBI's prior conclusions were reaffirmed.

"He was like a choir boy who turned into a devil," Giuliani said.

That level of disdain coincides with Trump's relentless campaign against Comey as special counsel Robert Mueller's Russia investigation intensifies. Comey's memo describing his previous interactions with Trump led to Deputy Attorney General Rod Rosenstein appointing Mueller in the days after Trump fired the FBI director. In turn, Giuliani has taken to deeply criticizing Comey on behalf of the president.

During a recent appearance on ABC's "This Week," Giuliani said Mueller seems to be more likely to believe Comey's version of events surrounding his firing than Trump's. Trump previously told NBC News that the Russia investigation, which Comey oversaw, played a role in his firing, even though the initial reason provided was Comey's handling of the Clinton email investigation.

"The special counsel so far seems to think that Comey is Moses," Giuliani said. "And I happen to think Comey is Judas."

'I used to be one of his star prosecutors. It appears I'm not anymore.'

Comey, who declined a request for comment from Business Insider, has responded to the recent criticism. Comey joked that he guessed "the love is gone" between the two from their time working together in the US attorney's office.

"I used to be one of his star prosecutors," he said during an event last month with The Washington Post. "It appears I'm not anymore."

Comey wrote about Giuliani at length in his recently released book, "A Higher Loyalty: Truth, Lies, and Leadership," in which he both expressed his admiration for Giuliani and decried his leadership style.

"There was something of an unwritten code about working in the office of Rudy Giuliani, as I suppose there is in most organizations," Comey wrote. "In his case, the message was that Rudy was the star at the top and the successes of the office flowed in his direction. You violated this code at your peril."

Comey wrote that Giuliani "had extraordinary confidence" and Comey "found his brash style exciting."

"I loved it that my boss was on magazine covers standing on the courthouse steps with his hands on his hips, as if he ruled the world," Comey wrote. "It fired me up."

But he later wrote that it took him "a while to realize that Giuliani's confidence was not leavened with a whole lot of humility."

Comey's commentary on Giuliani was surprising to some. James Gagliano, a former FBI agent who worked in the New York office for 20 years, told Politico that Comey's passages on Giuliani "jumped out at" him.

"Every mention he made of Giuliani" as US attorney, "there were gratuitous shots," Gagliano said, adding that it seemed like Comey "had an ax to grind with" Giuliani.

Giuliani, meanwhile, told Business Insider that Comey "was not that senior" and "wasn't involved when I was there."

"But I never heard anything bad about him," Giuliani continued. "He was a good guy. He did his work. I wasn't surprised when he moved up the ladder."

Now, Giuliani is "shocked" at Comey's "behavior," which he said "just gets worse and worse."

"And I think we're on the cusp of a very blistering report by the inspector general," Giuliani added, pointing to the Justice Department's inspector general report on the handling of the Clinton email investigation.

On Thursday, that report was released. Justice Department Inspector General Michael Horowitz wrote the Comey "deviated" from FBI and DOJ procedures in handling the Clinton probe, damaging law enforcement's image of impartiality. But, Horowitz wrote that Comey was not motivated by any political bias.

In his book, Comey wrote that no "fair-minded person with any experience in the counterespionage world" could think the Clinton investigation "was a case the career prosecutors at the Department of Justice might pursue."

"There was literally zero chance of that," he wrote.