Rudy Giuliani. Photo Credit:

In May of 1985, when Rudy Giuliani offered me a position as one of his assistants in the United States Attorney’s Office for the Southern District of New York, I was thrilled. It was the premier federal prosecutors’ office in the country, and even then Rudy’s fame preceded him. As a young assistant U.S. Attorney (“AUSA”) in the same office years before, he had made headlines, prosecuting corrupt NYPD narcotics officers in what would become known as the “Prince of the City” cases and had secured the conviction of Bertram Podell, a Brooklyn congressman, on bribery charges. Podell had been so flustered by Rudy’s aggressive cross-examination of him at trial, that he asked for a recess at the end of which he pleaded guilty. And so the legend of Rudy grew…….

I remember well my first day as an AUSA. I was instructed to arrive at 9 a.m. sharp and to bring whomever I wished with me to meet with Rudy in his private office prior to his swearing me in. I brought my beaming parents. Old Brooklynites, they listened eagerly as Rudy regaled them with the story of the Podell prosecution and then gave them what I later learned was one of his stock speeches concerning the proliferation of, and the need to aggressively investigate and prosecute, white collar crime. There is enough fraud going on on Wall Street, said Rudy, that if all of my assistants devoted all of their time to it, it might not even make a dent. But, he said, we have to try. And we have to use the same tools we’ve been using on the mob and drug king-pins—undercover operatives, wiretaps, and search warrants—on white collar crooks. It was high time, he said, to take the gloves off when it came to fighting “crime in the suites.”

It was a heady time to be a Southern District AUSA. All at once, it seemed, there were any number of high-profile prosecutions going on—prosecutions of the  mob (including the famed “Pizza Connection” case targeting the leadership of the Sicilian Mafia and the “Commission Case” charging the heads of the five organized crime families comprising La Cosa Nostra), prosecutions of securities fraudsters (including those of Ivan Boesky and Michael Miliken), and prosecutions of corrupt public officials (including the Wedtech cases ensnaring Bronx Congressmen Mario Biaggi and Robert Garcia and the Parking Violations Bureau case, which Rudy prosecuted himself, cross-examining and convicting Stanley Friedman, the Bronx Democratic leader).

Beyond all of that, as a young prosecutor, working for Rudy was fun and exciting. He had a great sense of humor, was smart, energetic, supportive. When you went into court to do battle, whether with unscrupulous defense attorneys or irascible judges, he always had your back. And he infused “the Office” with his professed ethos by repeating a mantra: “We always try to do the right thing for the right reasons.”

Then, at the beginning of 1989, Rudy stepped down from his position as U.S. Attorney. And in the years that followed, as he sought ever greater fame and fortune, he morphed into someone entirely different, almost unrecognizable. What happened after he left the prosecutor’s office, his subsequent history in both the public and private sectors, is worth repeating at this point.

Rudy ran three times for the mayoralty in New York City, the last two times successfully. By his second term as mayor, though, the city had grown weary of him and his “my way or the highway” style of governance. No matter; Rudy, term-limited, had already set his sights on higher office. In April of 1999, he formed an exploratory committee to run for the U.S. Senate seat vacated by Daniel Patrick Moynihan. A year later, his campaign—against Hillary Clinton—devolved into shambles and he pulled out of the race.

Then came 9/11. Rudy valiantly lead the city through the darkest moments in its history, earning him the epithet—from Oprah, no less—of “America’s Mayor.” Even here, however, Rudy’s ever-growing sense of self-importance and zeal for power were on display. He sought an unprecedented emergency extension of his term because, apparently, only he could save the city from the tragedy that had befallen it. Fortunately, cooler heads prevailed; Michael Bloomberg, who won the November election, took office in the ordinary course on January 1, 2002; and the city somehow managed to recover and prosper without Rudy at its helm.

With no office left to run for at the moment, Rudy decided to trade on his reputation as “America’s Mayor” and cash it in for big bucks. He set up Giuliani Partners, a private investigation/security firm, and Bracewell Giuliani, a law firm, and made a fortune from both. With more money in the bank than he could ever spend, Rudy, ever on the lookout for more power and acclaim, finally laid eyes on the presidency. In November 2006, he announced the formation of an exploratory committee toward a run for president of the United States and in February 2007 confirmed that he was indeed running. A year later, after a disastrous showing in the Florida primary, he pulled out of that  race, his very last.

Since Rudy abandoned the pursuit of electoral office—or, more accurately put, since the electorate abandoned him—he has struggled, desperately, to remain relevant, in the limelight, in a position of power. But, it seems, the more he struggles to do so, the more outlandish the things he says. Whether on the hustings for others, or as a talking head on cable television “news” programs, or as a criminal defense attorney, he has made statements that are arguably racist, false, and/or outright nonsensical. Examples abound.

At a Republican fund-raising event in February 2015, Rudy hatefully opined of our first African-American president: “I do not believe, and I know this is a horrible thing to say, but I do not believe that the president [Barack Obama] loves America…. He doesn’t love you. And he doesn’t love me. He wasn’t brought up the way you were brought up and I was brought up, through love of this country.”

In August 2016, campaigning for Trump at an Ohio event, Rudy astonishingly declared: “Before Obama came along, we didn’t have any successful radical Islamic terrorist attack inside the United States….” This from the man who led the city after 9/11 and was crowned “America’s Mayor” as a result of his leadership after that historic calamity.

In May of this year, Rudy, who had envisioned himself Trump’s Secretary of State, but who is now his lawyer/p.r. agent in connection with multiple criminal investigations—the same Rudy who in August of 1985 lectured my parents on the need to get tough on white collar crime and the need to use aggressive investigative tactics like search warrants on white collar criminals—referred to the FBI agents who executed the search warrants on Trump lawyer Michael Cohen’s offices and residence (warrants approved by the Acting United States Attorney for the Southern District of New York, the Deputy Attorney General of the United States—a Republican appointed by Trump—and a federal magistrate judge) as “storm troopers.”

Later that same month, appearing on This Week With George Stephanopolous, Rudy gave answers to the moderator’s questions that amounted to incoherent drivel, referring to a statement he himself had made days earlier explaining how Trump had reimbursed Michael Cohen for the latter’s $130,000 payment of hush money to porn star Stormy Daniels as a “rumor.”

Finally, just days ago, with evidence mounting that the Trump campaign knowingly accepted Russian offers of assistance, Rudy added new spin to his boss’ favorite tweet, “No Collusion!” Said Rudy in an interview on Fox & Friends: “I have been sitting here looking in the federal code trying to find collusion as a crime….Collusion is not a crime.”

That’s right Rudy. “Collusion” is not a federal crime. But—and this goes to only one of the many allegations Special Counsel Robert Mueller is investigating—the knowing and willful acceptance of a campaign contribution in the form of money or a thing of value (including negative information about an opponent, hacked emails and the like) from a foreign national is. As Yankee great Casey Stengel used to say, “You could look it up.” See Title 52, United States Code, Sections 30121 & 30109. And Rudy might also want take a look at the order appointing Mueller. The word “collusion” doesn’t appear anywhere within the four corners of the document. “Collusion” is just a straw man set up by Trumpistas to be knocked down by Trumpistas.

It has been said that when Rudy was in college he considered entering the priesthood. One wonders what his religious tenets are now, in his senescence, other than self-aggrandizement, pursuit of the almighty buck, and unquenchable lust for power. What happened to Rudy Giuliani? Where is the sharp-as-a-tack, reform-minded, valiant corruption fighter who was one of my mentors and role models? Where has that man gone who exhorted us to do the right thing for the right reasons? As I look back over the arc of Rudy’s career—the Rise and Fall of Rudy Giuliani—I can sum it up in one word that he, a Trump sycophant, can undoubtedly understand: “Sad!”

Elliott B. Jacobson retired from the United States Attorney’s Office in March of 2017 after serving under eleven successive United States attorneys.