He was, to the popular eye, Eliot Ness reincarnated, an unsparing prosecutor for a crime-shadowed age. And when the United States attorney in Manhattan resigned in January 1989, he earned a tabloid salute:
“Good News for Bad Guys,” The Daily News proclaimed. “Crimebuster Giuliani Steps Down.”
Rudolph W. Giuliani waved his prosecutor’s scythe in the 1980s, and Wall Street barons, political bosses and Mafia dons seemed to fall in serried rows. He inspired cinematic characters, took ovations in restaurants and battled the Reagan administration officials who had appointed him.
Michael Dowd, a streetwise lawyer whose trial testimony about bribe-taking exposed the ethical rot afflicting New York politics, found shelter beneath Mr. Giuliani’s cloak. “No one was going to back him off,” Mr. Dowd said. “He was charismatic, relentless and endlessly loyal.”
There was, however, another side to the young prosecutor, a moralistic and carnivorously ambitious man who desired public office. Mr. Giuliani, who was 38 when he became United States attorney in 1983, threatened his targets with long prison sentences, and he infuriated judges with leaks of grand jury testimony to the press.
His agents handcuffed Wall Street arbitrageurs before prosecutors investigated them. Apology was weakness; skeptics were “jerks.”
Like a medieval crusader, he rarely flinched at hard tactics in pursuit of exalted goals.
In 1987, about 50 armed marshals raided and locked down the investment firm Princeton/Newport Partners. A federal appellate court overturned that racketeering conviction, but the firm remained shuttered. “We were in the wrong place at the wrong time,” said financier Jay Regan, a principal at Princeton/Newport. “It’s strange to be sacrificed on someone’s altar.”
There are three founding stones in the public career of Rudolph Giuliani: His performance during the terror attacks of 9/11; his image as a crime-fighting mayor of New York; and his nearly five-year tenure as United States attorney. It was in this earliest incarnation that Mr. Giuliani is most plainly seen in the rawness of his promise and drive.
He possessed a junkyard-dog toughness and moral clarity that left his deputies exhilarated. Action, he told them, was preferable to hesitation, and so they laid low the mob and pressed reform on Wall Street.
Mr. Giuliani called his lawyers “the Yankees,” and he had the swagger of a team manager. “If you had offered me one job in government, I would not have said mayor, I would not have said president, I would have said prosecutor,” Mr. Giuliani said in a recent interview. “It’s really an ideal job for an idealistic man; you never have to do the wrong thing.”
Mr. Giuliani armored himself with a tight band of lawyers and investigators, men known as the “Yes Rudys!” One of them tended to the prosecutor’s political future, another to the deputies, a third handled leaks to the press. They shared cigars and drinks in the evening.
The timing of his ascension was fortuitous. The F.B.I. had completed an investigation of the Mafia that would provide the grist for several major prosecutions. Federal prosecutors in Chicago passed along a tip about bribery in New York City that stood municipal government on its head. Federal investigators were already investigating Wall Street corruption.
And a decade earlier Congress had permitted the resumption of wiretaps and had passed an anti-racketeering law that allowed prosecutors to take aim at crime bosses and their wealth rather than fishing for flunkies.
Those who worked with Mr. Giuliani came away impressed by his intuitive grasp of his new arsenal.
“Rudy was a sponge, willing to sop up any idea, any new strategy,” said G. Robert Blakey, a law professor at the University of Notre Dame, who crafted the anti-racketeering law as a consultant for the Senate Judiciary Committee. “He was very creative about wielding power.”
Mr. Giuliani married aggressiveness to moral absolutes, reflecting his steeping, he said, in the Catholic catechism. Asked about political corruption in 1987, he offered a wintry smile and said, “I don’t think there’s anybody much worse than a public official who sells his office, except maybe for a murderer.”
But many judges, lawyers and professors questioned Mr. Giuliani’s temperament and judgment, and their concerns linger. His pursuit of a political career while commanding the prosecutor’s stage stirred deep unease.
“We depend on prosecutors being capable of doubt and exercising discretion,” said Stephen Gillers, a professor of legal ethics at New York University and a former law school classmate of Mr. Giuliani’s. “You can’t push the throttle forward every time, and that’s what he did.”
Building a reputation
Mr. Giuliani was a husky young assistant federal prosecutor who was almost painfully hungry to make his mark in 1974. That was the year that he prosecuted United States Representative Bertram L. Podell of Brooklyn on conspiracy charges.
Mr. Giuliani described going at him like a boxer during the trial. “The next day, withering under continued cross-examination,” Mr. Giuliani wrote in his 2002 book, “Leadership,” “he asked for a recess, during which his lawyer told us he had decided to plead guilty.”
The recollections of the congressman’s lawyers are less dramatic. They had already reached a tentative plea deal, they said, and were simply awaiting Justice Department sign-off when Mr. Giuliani began his cross-examination. The deal went through during a recess.
“With all due respect, Rudy is a good trial lawyer, but there was no awakening of the congressman’s spirit,” said James M. LaRossa, who represented Mr. Podell during the trial. “That story is out of whole cloth.”
Mr. Giuliani applied for a judgeship while in his early 30s, then catapulted, with the help of influential mentors, into the high reaches of Ronald Reagan’s Justice Department. In 1983, he became the United States attorney for the Southern District of New York, the most prestigious such posting in the nation.
The Justice Department “thought I was unhappy” about living and working in Washington, Mr. Giuliani recalled in the interview. “I said, ‘No, no, you don’t understand. I could do things with that office that haven’t been done.’”
Mr. Giuliani’s legal kingdom stretched from Manhattan to counties further north, and he insinuated himself into every corner of New York City. In the Brownsville section of Brooklyn, a poor neighborhood, Manhattan-based union leaders were shaking down East Brooklyn Churches, a group that was building affordable houses. The ministers appealed to the new prosecutor.
Mr. Giuliani began an investigation and obtained indictments.
“He made the unindicted machine hacks and graying Village progressives look like wax figures,” Michael Gecan, an organizer with the group, recalled in his book, “Going Public.”
Mr. Giuliani’s wife at the time, Donna Hanover, was a television anchor, and they cultivated reporters like gardeners tending flowers. He sat for interviews that ran for hours. Announcements were timed for the 6 o’clock news.
He became known in the press as “the New Untouchable,” the “priestly prosecutor.”
The coziness with the press chilled others. Nat Hentoff, a columnist for The Village Voice, said that Mr. Giuliani once listed for reporters the officials he was likely to indict. Wayne Barrett, author of “Rudy! An Investigative Biography of Rudolph Giuliani,” said leaks came from those around Mr. Giuliani.
“Out of Rudy’s mouth? He was very careful,” Mr. Barrett said. “But people in his office would show you things that were completely illegal.”
Federal judges lashed Mr. Giuliani’s office for leaks. Judge Whitman Knapp declared in a 1986 ruling in one of Mr. Giuliani’s cases: “It may well be that the attorney general of the United States would be interested in ascertaining which of his employees was engaged in violating one or more of the statutes he or she was sworn to uphold.”
Walter Mack, chief of the office’s organized crime unit until Mr. Giuliani replaced him, watched camera crews troop by his office.
“There was a strong view that our office’s power was abused for political purposes,” said Mr. Mack, who, despite his history with Mr. Giuliani, supports his former boss’ presidential bid. “If you have in mind a career in politics, maybe self-abnegation has its limits.”
Nothing so defined Mr. Giuliani as his decision to toss his full weight against the five Mafia families. He had an epiphany in the early 1980s, he said, while reading a mob biography in his Washington apartment.
“I dreamed up the tactic of using the federal Racketeer Influenced and Corrupt Organizations Act,” he said in “Leadership,” “to prosecute the Mafia leadership.”
Few former federal officials credit his story. The Federal Bureau of Investigation had accumulated reams of taped evidence by that time, from bugs planted within cars and social clubs. Federal prosecutors in Brooklyn had already brought RICO cases.
“His claim that he revolutionized prosecutions is preposterous,” said Edward A. McDonald, a former chief of the federal Organized Crime Strike Force in Brooklyn. “Rudy’s epiphany came from reading F.B.I. wiretap applications.”
Mr. Giuliani conceived of a case of great sweep and persuaded the Justice Department to let him poach cases from Mr. McDonald’s shop. He indicted eight leaders of La Cosa Nostra, and jailed most of them.
Mr. Blakey of Notre Dame is philosophical about the complaints lodged against Mr. Giuliani. Did he find great raw material sitting there? Sure. And so what? “This is a merry-go-round; the golden ring only comes once,” Mr. Blakey said. “You grab it or you miss. Rudy didn’t miss.”
Mr. LaRossa describes himself as a “non-white-collar criminal defense attorney,” and Mr. Giuliani was the beginning of the end for his mob clients. He is inclined to tip his fedora.
“Other than Paul Castellano, who was shot dead outside a steakhouse, they all went to prison,” Mr. LaRossa said. “It’s hard to argue with that track record, O.K.?”
Wall Street, 1987
In February 1987 federal agents walked into the plush confines of the arbitrage department at Goldman Sachs & Company. They found Robert A. Freeman, who led the department, in his glass-enclosed office and escorted him outside the building, where they placed handcuffs around his wrists.
Richard B. Wigton, 52, a vice president at Kidder, Peabody & Company, was handcuffed in his office. Timothy L. Tabor, a former vice president at Kidder, spent the night in jail. All three were accused of insider trading.
To arrest white-collar defendants rather than asking them to surrender was unusual. On the other hand, when the time came to indict Mr. Castellano, the Gambino crime family chieftain, he was allowed to pick up a coat and buy a candy bar before turning himself in.
Mr. Giuliani waved off complaints. These men, he said without offering evidence, could have fled. “This isn’t,” he said, “an invitation to a party.”
Mr. Giuliani has made millions of dollars speaking to corporations since 2001 and has raised bundles of political contributions on Wall Street. He rarely talks of his financial sector prosecutions anymore. (In “Leadership,” he said he indicted Michael Milken, a top executive at Drexel Burnham Lambert, and “prostate cancer reunited us.”)
But he once surfed a wave of popular revulsion with Wall Street. It fit his worldview: He would restore “ethics and morality” to this dark land. He treated stockbrokers, rhetorically and legally, as gangsters, replete with RICO cases.
His crowbar tactics had a rough logic. Financiers are tough prey, safeguarded by the finest lawyers. His deputies threatened to chase down targets and worry about untangling the details later.
“The benefit was that people cooperated a lot quicker when the cases were treated aggressively,” said Edward J. M. Little, a former Giuliani deputy. “No one got hurt except those who richly deserved it.”
That judgment depends on one’s perspective. Gerald B. Lefcourt, a defense lawyer, talked with prosecutors after the Princeton/Newport raid. He was particularly disturbed that prosecutors applied a law intended for mobsters to the highly technical world of Wall Street finance.
“Rudy told me that my client would face 40 years in prison and a forfeiture of his assets,” said Mr. Lefcourt, who represented one of the Princeton/Newport defendants. “That strikes me as quite dangerous and unconstitutional.”
The courts overturned the racketeering case against Princeton/Newport and, in a separate case, tossed out the insider trading conviction of the stockbroker John Mulheren.
Mr. Giuliani also cut generous deals with those who cooperated with him. (“Minimal sentences for maximal felons,” the columnist Murray Kempton wrote in Newsday.) Ivan Boesky, the Wall Street arbitrageur, admitted making more than $100 million with stolen information. Yet he pleaded guilty to a single securities violation and kept his foreign bank and brokerage accounts. In return, he agreed to provide evidence against other people.
Martin A. Siegel, also of Drexel Burnham Lambert, took suitcases of cash from Mr. Boesky and was sentenced to two months in prison in exchange for offering to inform on Mr. Freeman, Mr. Wigton and Mr. Tabor.
Prosecutors authorized their arrests before turning to the grand jury. Mr. Giuliani later dropped the indictments, but vowed to bring bigger ones. “This is the tip of the iceberg,” Mr. Giuliani said.
He found no iceberg.
In August 1989, the United States attorney’s office announced that Mr. Tabor and Mr. Wigton would not be charged. “I exercised to the best of my power the power of mercy,” Mr. Giuliani added. “That doesn’t mean I didn’t get it wrong sometimes.”
As for Mr. Freeman, he passed a lie detector test, and none of Mr. Siegel’s allegations held up to legal scrutiny. Investigators with the Securities and Exchange Commission examined Mr. Freeman’s case years later and, in an extraordinary move, let him resume his career. By that time, he had pleaded guilty to a count of mail fraud. He had taken a glum view of his chances at trial.
“It was truly a surreal experience,” Mr. Freeman said yesterday.
“Had the prosecutors conducted an even cursory examination of the evidence prior to the arrests,” he added, “this whole tragedy could have been avoided.”
Rooting out corruption
New Haven in the autumn of 1986 was a moveable feast of preening and posturing. Each evening, two lions of the New York defense bar, Mr. Lefcourt and Thomas Puccio, would descend the federal courthouse stairs. Within earshot of each other, they would brag of their courtroom triumphs. Mr. Giuliani, uncharacteristically, kept a low profile.
They had come to New Haven to try a political corruption case with many tentacles: The sardonic Bronx Democratic leader Stanley Friedman, a close ally of Mayor Edward I. Koch, stood accused of racketeering.
Mr. Puccio, who defended Mr. Friedman, had demanded that the trial be moved out of New York to a city that was untainted by the prosecutor’s “prejudicial statements.”
Mr. Giuliani did not argue the point. “Rudy knew that juries outside New York were more pro-government,” said David Zornow, one of Giuliani’s deputies who worked that case. “His instinct was: ‘Fine, let’s do it. It will be a pox on these New York guys.’”
But it was a defendant’s hubris that was the trial’s turning point.
Mr. Giuliani accused Mr. Friedman of profiteering: “You got paid $10,000 to make two calls on behalf of the taxi drivers’ association?”
“That was one call, Mr. Giuliani,” Mr. Friedman said.
The trial might as well have ended there. Mr. Friedman was convicted and served four years in prison.
It was during this trial, Mr. Giuliani has said, that he first thought of running for mayor. A year later, he weighed a campaign against Senator Daniel Patrick Moynihan. All the while, he brought cases against politicians who had corrupted their offices.
In 1987, United States Representative Mario Biaggi was accused of selling his influence to win business for a Bronx defense contractor, Wedtech. To defuse charges that this prosecution was politically motivated (Mr. Biaggi was a Democrat) the prosecutor, Mr. Little, decided to invoke Attorney General Edwin Meese III, a Republican who was a close friend of a Wedtech lobbyist — and Mr. Giuliani’s boss.
Mr. Little bumped into his boss, Mr. Giuliani. “I’m going to have to tell that jury that Ed Meese is a ‘sleaze,’” Mr. Little said.
Mr. Giuliani smiled quizzically. “Are you really going to do that? Do you really need to?”
I’m afraid so, Mr. Little said.
Do it, Mr. Giuliani said.
A goodbye salute
On a frosty January day in 1989, with his first mayoral race looming, Mr. Giuliani assembled his staff in the library at the United States attorney’s office and offered a goodbye salute. The once-chubby prosecutor now was almost gaunt, a thinning shock of dark hair combed across his scalp.
Look, he said, here’s what I have to say about my time here. We may have made our mistakes along the way, but I don’t think we ever made mistakes for the wrong reason.
Mr. Giuliani has held tight to that image, the jaunty chieftain and his legal warriors, many of whom have remained admirers and, in some cases advisers. But those who battled him remember most of all his near-overwhelming moral certitude.
It still troubles some.
“The public wants to see tough prosecutors, but being tough is not always best,” said Mr. McDonald, the former prosecutor who led the Organized Crime Strike Force. “If you’re always concerned with looking tough, you’re not always looking to be fair. I wonder about that balance.”