It is a musty notion from a bygone era, but once upon a time the idea that Rudy Giuliani and Donald Trump could be a tag team in search of political dirt on common enemies was as foreign as the Ukrainian soil they now till.
In the New York of the 1980s, when both rose to prominence, they were at opposite poles of the civic landscape.
One was a swaggering crime-buster taking down Mafia bosses, Wall Street predators, and corrupt politicians. The other was a rules-bending real estate tycoon, a shiny emblem of the age of Greed Is Good, bent on success at any cost.
Yet both reveled in public brazenness. Giuliani walked stockbrokers off the trading floor in handcuffs. Trump ripped down precious landmarks to make way for his buildings. Both were also fluent in the language spoken among the elite of New York deal-makers, where favors are traded, punches are pulled, and the public interest always finishes a dismal last.
And as laughingly obvious as it is today, those of us back then who cheered on the prosecutor, while raking the muck on the developer, eventually learned the hard way that these two were cut from the same cloth, destined for a partnership far more enduring than their many marriages.
The first glimmerings of that lesson surfaced one night in an Italian restaurant in Greenwich Village as Jack Newfield, the legendary investigative digger, and I dined with a federal agent named Tony Lombardi.
Although technically employed by the Internal Revenue Service, Lombardi’s only apparent duties were to serve as the trusted special investigator for Giuliani, then the hard-charging United States Attorney for the Southern District of New York.
While Giuliani had at his beck and call a squad of FBI agents and other investigators, he preferred Lombardi for sensitive assignments. It was Lombardi, a dapper man given to double-breasted suits and pocket hankies, who was asked to look afte the unstable daughter of a judge facing corruption charges, who had been persuaded to provide testimony for the prosecution against her own mother. It was Lombardi who was detailed to work on an investigation into city contracts granted to a health consultant rumored to have been the lover of Mayor Ed Koch, against whom Giuliani was then pondering a campaign.
Along with a bevy of other local reporters, we knew that Tony Lombardi was, as our friend and Village Voice colleague Wayne Barrett dubbed him, “the eyes, ears and mouth of Rudy Giuliani.”
That night, amid the opening pleasantries, Lombardi shot the French cuffs from his suit jacket, leaned forward on the table, and announced: “I have another year or so to go with the department, and then I’m going to be head of security for Donald.”
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No last name was needed to explain this promising exit plan from public service. This was 1988, and Donald Trump had forced himself into public consciousness like the car alarms that blared mercilessly without stop. He had already put his name on a soaring tower in midtown, repaired an ailing city skating rink in Central Park, launched casinos in Atlantic City, and publicly toyed with the idea of running for president.
Lombardi’s comment was decidedly off-kilter with what was on the menu that evening. Two years earlier, Giuliani had won convictions against a ring of scoundrels who had been happily looting city coffers under the nose of the Koch administration. Most prominent among his scalps was that of Stanley Friedman, the goateed Democratic Party chieftain from the Bronx who had been nailed while attempting a flimflam worth millions on the city’s transportation department.
A former deputy mayor, Friedman had been a partner in the law firm of Roy Cohn: Senator Joseph McCarthy’s Iago, a master of the legal dark arts, and lawyer to some of the biggest mobsters Giuliani was simultaneously pursuing. While Friedman had worked from the top floor of Cohn’s East Side townhouse and law office, Cohn had been on the ground floor offering lessons in the use of bluster, bravado, and outright lies to his prize client and pupil, Donald Trump.
If Rudy Giuliani was the anti-corruption scourge of New York, Cohn’s budding protégé should have been a likely suspect, even a prized quarry.
At the table, Lombardi offered no details about how his richly rewarding job offer had arisen. In the course of business, he said, he had come to know Trump. The two had grown friendly. The discussion then moved on to more pressing matters.
It wasn’t until several years later, thanks to the steady drilling of Barrett and fellow Voice reporter William Bastone, that we learned the back story: At the time of our meeting, Lombardi had recently finished a quiet inquiry on behalf of his boss into allegations that organized crime figures had laundered hefty sums of cash as they bought apartments in Trump Tower, the flagship of the developer’s then-growing empire.
The charge had come froma mob-tied financial consultant facing a federal tax fraud indictment looking to help himself by offering to tell a far more interesting story. The consultant said he had helped the underworld figures—most notoriously, Robert Hopkins, a numbers kingpin working for the Luchese crime family—buy the apartments at Trump’s complex with fraudulent mortgages. The developer himself, the consultant alleged, had been present as suitcases of cash had changed hands at Hopkins’s closing.
The purchase landed Hopkins two apartments worth $2 million on the upper floors of Trump Tower. That’s where the Manhattan DA found him when he was arrested in 1986, charged with orchestrating a mob hit. Hopkins’s defense lawyer? Another partner of Roy Cohn.
This was potentially rich Giuliani territory: the Mafia, bank fraud, and a possibly complicit high-profile figure. But the investigation ended before it even began. Instead of building a case by working his way through knowledgeable witnesses and records, Lombardi went straight to Trump himself with the allegation. He was quickly won over. As the agent later told Barrett in a 1993 Voice story about the episode, he was so impressed with Trump’s openness and honesty that he decided there was nothing to investigate. “The guy met me without an attorney,” Lombardi said. “He answered all my questions. There was never any hesitation.”
All of this, Lombardi insisted, was done with the approval of higher-ups at the US Attorney’s office. “[E]veryone that should have known about this thing knew,” he said.
There was another possible reason for the sudden lack of prosecutorial interest. That spring, Trump began touting Giuliani as a would-be mayor, claiming he could raise $2 million in a half hour if the US Attorney decided to run.
Of course, that was just Trump spin. He did briefly back Giuliani and raised a few thousand for his failed 1989 race, but by 1993 Trump was hedging his bets, hoping for approvals by David Dinkins, the sitting mayor, for his pending projects.
Things didn’t work out for Tony Lombardi in the end. An internal investigation by the IRS faulted him for engaging in prohibited fundraising for Giuliani and abusing his authority with sources. He wound up jilted by Trump, who gave the security job to someone else, and by Giuliani, who never offered him even a nominal post in City Hall. Lombardi died in 2015.
Giuliani now works feverishly on behalf of the man he once investigated. Eyes bulging, waving his phone with McCarthy-like flair as he insists it holds all the damning information he has discovered, he thunders away on the talk shows. Once-loyal fans say they hardly recognize that man. But he’s not the one who has changed. He is the same zealous, win-at-any-cost inquisitor he always was, a genuine “Made in New York” schemer. Just like his client.
