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The Long, Cruel Career of Rudy Giuliani

After decades of polluting the political landscape with authoritarianism and race-baiting, is Rudy Giuliani's career finally over?

Rudy Giuliani speaks at a Donald Trump event in Phoenix in August 2016. Gage Skidmore / Flickr

Over the course of a four-decade-long career, Rudy Giuliani has gone by many monikers (“Rudy,” “America’s Mayor”) and picked up and dropped even more personas: the hard-charging public prosecutor cracking down on mob bosses, corrupt politicians, and white-collar criminals; the crime-busting mayor for whom no misdeed was too petty to discipline; the Churchillian leader who shored up a nation’s courage in the midst of attack; the well-connected corporate lawyer who greased the wheels for a parade of special interests.

For a while, it looked like Giuliani was poised to add yet another designation to this formidable track record: secretary of state, or at least a top position of some kind, in the Trump administration.

But it was not to be. On Friday, Trump announced that Giuliani had removed his name from consideration — not just for secretary of state, but for any cabinet position. Giuliani later explained that his “desire to be in the cabinet was great, but it wasn’t that great,” and that once the field expanded and he was happy with the candidates, “there was no reason to complicate [Trump’s] life any longer.”

Giuliani’s comments are likely an attempt to save face after campaigning aggressively for the secretary of state job, only to be eclipsed in recent weeks. It must have been a bitter disappointment for a man who spent 2016 transforming himself into an implacable yes-man for Trump, willing to appear on virtually any public platform and paper over (or even defend) his candidate’s latest remarks, no matter how odious.

For most of the campaign, when the vast majority of media commentators saw the Trump campaign as a dangerous yet slowly sinking ship, Giuliani’s sycophantic role was viewed as the final debasement of an otherwise relatively respectable, even venerable, legacy — the “appalling last act” of a man who was once the country’s most popular politician. In the wake of Trump’s election, his actions seem more like one final, risky (and ultimately unsuccessful) bid for power.

But Giuliani’s career and legacy were also never as pristine as many commentators would have the public believe. Over the course of his chameleon-like political career, Giuliani displayed an authoritarian streak and penchant for corrupt deal-making that should’ve disqualified him from having his hands anywhere near the levers of power.

In fact, as nightmarish as Trump’s team already is — rife with racists and union-busters and plutocrats — a thorough look at Giuliani’s record shows that his presence could have made it even worse.

Animosity for Asylum

Giuliani’s career bore a black mark from the start, when he was put in charge of Reagan’s Haitian refugee policy. The episode is a sobering glimpse at what could have been if Trump had nominated Giuliani.

A “Robert Kennedy Democrat” for most of his life, Giuliani switched party allegiances in early 1981 — just in time for the newly inaugurated Ronald Reagan to appoint him the number three person in the Justice Department. He was tasked with spearheading the administration’s response to the ongoing Haitian refugee crisis. Each month, around 1,500 Haitians were arriving in Florida fleeing political repression and crushing poverty.

Even though vastly more Cubans were streaming into the US at the time — 125,000 in less than a year compared to 40,000 Haitians over the previous ten years — the Reagan and Carter administrations greeted the Cubans with relatively open arms.

The Haitians absconding from “Baby Doc” Duvalier’s Haiti met a different fate. Giuliani negotiated an agreement with the Coast Guard to intercept incoming Haitian ships and send them back. Refugees, risking everything to board ramshackle boats that often capsized, were forced to return to the place they were so desperate to escape.

The Haitians that managed to reach the States were placed in overcrowded detention centers. Some were shipped to Puerto Rico’s Fort Allen, which an attorney fighting the decision warned would be “used as a concentration camp” and wasn’t fit for humans.

It was the Krome detention center in Miami that earned the most notoriety, however. Thousands of refugees were kept in overcrowded conditions, some longer than eighteen months. Those detained at Krome eventually launched a hunger strike and attempted to escape. But while one top official admitted the refugees were in “jail,” Giuliani dissented, arguing the refugees were “not held behind bars.”

Ronald Reagan with Rudy Giuliani. dis magazine

Giuliani also insisted the refugees were economic refugees, not political ones — a crucial distinction, as the latter necessitated that the US grant them asylum. “They left because they were starving,” he said, and so “do not fit the definition of refugee.” In court, Giuliani (falsely) claimed that “no political repression” existed in Haiti and that he had received a personal assurance from Duvalier that returning refugees weren’t being persecuted. “There is not a problem, a major problem, a systematic problem of political repression in Haiti,” he testified.

The core issue, Giuliani told Barron’s National Business and Financial Weekly in 1983, was the country’s ability to control its own borders, as well as the rights of those immigrants who came to the US legally — who “play by the rules and have not gotten into boats and planes and crashed in.” Giuliani saw himself as the victim, professing that he “was personally hurt” that people were accusing him of being a racist.

He complained that television cameras “would show these pathetic people sort of holding hands and kissing each other, and then say that this man and wife were separated by this cruel vicious government.” But, he said, “these people don’t come over with marriage certificates,” and “they keep claiming that different people are their wives.” He added that “if you let the men into the women’s camps, they go around raping them.”

Giuliani’s actions under Reagan showed a disturbing willingness to crack down on not just refugees, but society’s most marginalized. And of course, immigration was just one area in which Giuliani meted out draconian measures against those he viewed as the enemy.

Crusading Against Crime

No account of Giuliani’s career is complete without examining his record on crime. For much of his early career, the name “Giuliani” was synonymous with an aggressive, uncompromising — one might say pathological — posture toward lawbreaking.

Giuliani first catapulted into the nation’s consciousness as a take-no-prisoners United States attorney for the Southern District of New York — technically a demotion from his previous post in the Justice Department, but one he eagerly pursued, likely owing to the national platform it gave him. He soon built a reputation as a relentless crimebuster who zealously attacked criminal wrongdoing wherever it reared its head.

Giuliani’s work in the US attorney’s office deserves some credit. He took on corrupt politicians, put the heads of New York’s five mafia families behind bars, and cracked down on white-collar crime, earning himself plenty of headlines in the process. One of his chief claims to fame was his innovative use of the RICO statute to target mob bosses, and even bankers. Even if he didn’t “dream up” the strategy like he claimed, his adoption of it was still significant. And even if the number of prosecutions he later boasted about were less impressive than he made them seem, his formidable record as a prosecutor is undeniable.

But it came at a cost. In the process of taking the fight to well-heeled criminals — and tirelessly chasing the associated publicity — Giuliani often ran roughshod over basic civil liberties.

Amid a sea of fawning profiles of Giuliani in the 1980s, the New York Civil Liberties Union’s Richard Emery sounded the alarm, accusing Giuliani in an op-ed of resorting “to an array of extreme measures that threaten the presumption of innocence and the right to an adequate defense in six criminal trials.” These included freezing the assets of the accused (thereby restricting their ability to pay for attorneys) and using “carefully orchestrated press conferences, news releases and luridly phrased indictments” to convict them in the court of public opinion.

In one infamous incident, Giuliani used allegations of tax fraud to indict the investment firm Princeton/Newport Partners on racketeering charges. He dispatched fifty armed federal marshals kitted out in bulletproof vests to raid and lock down its offices, and demanded pretrial forfeitures worth tens of millions of dollars, prompting spooked investors to abandon the firm, which was consequently liquidated. Despite the hoopla, the firm’s conviction was later overturned on appeal, and the IRS found it had actually overpaid its taxes.

Granted, investment bankers aren’t the most sympathetic of victims. But just imagine that kind of unchecked power turned against, say, a civil rights organization.

The Princeton/Newport case wasn’t the only one of Giuliani’s high-profile convictions that was eventually overturned. After Giuliani left the US attorney’s post in 1987, four of his white-collar cases were quashed, a nigh-unprecedented string of reversals. “You cannot read the appellate decisions without being disturbed by the way some of these cases were prosecuted,” journalist James Traub wrote in an otherwise sympathetic account at the time. One such questionable tactic: wiretapping a suspect’s defense attorney.

Giuliani’s time spent toeing the line between prosecutorial fervor and total disregard for legal niceties revealed authoritarian leanings that would only intensify upon winning the New York mayoralty in 1993. Once in office, he launched a full-fledged war on crime.

Giuliani outlined his law-and-order philosophy in an interview with New York magazine six years earlier. “[P]rotection against crime is going to emerge as the most important civil right in the country,” he said, “because if you don’t have protection against crime, all the other civil rights are basically academic matters.”

Giuliani’s language echoed the apocalyptic tone of an op-ed he had written for the New York Times four years prior, warning that the “Lower East Side as we know it, and as our parents and grandparents knew it, may disappear” and casting the city’s crime problem as a “territorial war” between “hard-working, law-abiding people” and “invaders” flooding the streets with drugs. Rather than getting at the root causes of crime, Giuliani’s solution was to punish offenders “with sentences that frighten those who might be contemplating such crimes.”

When he assumed the mayoralty, Giuliani put this vision into action. Under Giuliani’s “broken windows” theory of policing, he declared even panhandlers and squeegee operators targets of law enforcement. He instituted the ultimately unconstitutional policy of stop-and-frisk, which as early as 1999 was found by the attorney general’s office to be grossly discriminatory.

He nearly tripled the size of the NYPD’s Street Crime Unit, an elite squad of hundreds of officers who did the bulk of stopping and frisking, opening the doors to inexperienced, less well-trained officers to join the squad.

It was members of this unit (known for wearing T-shirts that read, “there is no hunting like the hunting of man”) who caused one of the biggest scandals of Giuliani’s mayoralty: the killing of Amadou Diallo. Officers fired at the innocent Guinean immigrant forty-one times after he pulled his wallet out of his pocket.

A protester holds an edition of the Daily News on Amadou Diallo’s death on February 15, 1999. Elvert Barnes / Flickr

It wasn’t just the rank and file who were the problem, however. The unit’s commanders at one point asked NYPD borough commanders to maintain lists of all West Indians they arrested in order to create a database of suspects.

Giuliani tried going even further in his second term, launching a “civility campaign,” that attempted to turn New York into a more polite, “civilized” city by force. The police, Giuliani decreed, would crack down on everything from littering, speeding, and loud car alarms to, perhaps most outrageously for New Yorkers, jaywalking. He also went after street artists and food vendors. Not surprisingly, the campaign proved toxic to his popularity.

For his supporters, Giuliani’s singular accomplishment as mayor was driving down New York’s sky-high crime rate. And indeed, in the years after Giuliani left office, the idea that his policies substantially reduced crime in the city was largely internalized by the press and public.

Today, there’s far less certainty. For one, crime had already started falling before Giuliani became mayor, dropping 16 percent over the last three years of the term of his predecessor, David Dinkins. (Giuliani nonetheless dismissed these numbers and attacked Dinkins as soft on crime.) Secondly, the fall-off in crime corresponded with a countrywide plunge in crime rates, including in cities with vastly different law enforcement policies.

At best, Giuliani implemented overzealous measures that may have saved some lives but also infringed on civil liberties. At worst, he unnecessarily erected an exceedingly punitive, highly discriminatory architecture for policing that regularly trampled on people’s rights.

But there’s little indication Giuliani ever had any regrets. This year, as one of Trump’s leading surrogates, he called for requiring anyone put on the government’s deeply flawed terror watch list to wear electronic monitoring tags. He also bragged about instructing police to spy on mosques, a policy he’s been advocating since at least 2014.

No doubt influenced by Giuliani’s advice, Trump has called for stop-and-frisk to be instituted nation-wide.

Admiring Authority

For Giuliani, carrying a badge and a gun has always granted one immunity from criticism. Time and again, whether the incident was murky or a clear case of police abuse, Giuliani defended law enforcement.

Barely two weeks into Giuliani’s mayoralty, two separate acts of police violence had community members up in arms. In the first, officers charged into a Harlem mosque after receiving what turned out to be a fake 911 call, leading to a brawl that injured eight officers and culminated in a tense standoff. Giuliani defended them to the hilt.

A day later, police killed an unarmed seventeen-year-old, claiming he had scuffled with an officer and then tried to run away. Giuliani immediately proclaimed that the “officer reacted both properly and bravely.”

Except neither eyewitnesses nor a forensic analysis backed up the officer’s story. Instead, witnesses said — and, according to the family’s lawyer, an autopsy later showed — that the boy had his hands up when police fired on him. The city later paid $318,000 to settle a lawsuit brought by the family.

These two incidents set the tone for an administration that virtually made shielding law enforcement from accountability official policy. According to journalist Wayne Barrett, who wrote a biography of Giuliani, only 5 percent of complaints to the Civilian Complaint Review Board were ever substantiated by the agency, and in two-thirds of the 635 cases reviewed between January 1996 and July 1998, the agency took no action against police. Even so, Giuliani proposed massive cuts to the agency in every one of his first four budgets (all were overridden by the city council).

Often, Giuliani was on the front lines, vocally admonishing the victims of police shootings. When sixteen-year-old Michael Jones was shot six times while carrying a toy gun, Giuliani contended that “adult supervision” would have kept him from going out in the middle of the night with a fake weapon. “I don’t think the purpose for which he was out was a salutary one,” he added. Giuliani doubled down when police shot sixteen-year-old Dante Johnson, deciding that the fact that they were “sixteen-year-olds at 12:30 in the morning” helped “explain and justify what happened here.”

On the day of the indictment for the four officers responsible in the Diallo killing, Giuliani gave a speech defending the “right to demand more respect from the citizens of the city for the police” and asserting that police were being “second-guessed by some of the worst in society.”

Most notoriously, after undercover police shot twenty-six-year-old Haitian immigrant Patrick Dorismond in an unnecessary confrontation that officers had incited, Giuliani launched what one author called a “one-man crusade to tarnish” his image. Giuliani authorized the public release of Dorismond’s arrest record and cautioned that “people do act in conformity very often with their prior behavior.”

Giuliani’s act quickly turned off the public. Yet he refused to budge. Barrett reported that after he secretly sat in on an all-white focus group of New Yorkers, who unanimously agreed that the mayor had handled the Diallo shooting poorly, Giuliani began shouting that the exercise was “a waste of time” and that he was “not going to turn against the police.”

Throughout his career, Giuliani has switched positions on a dime when it threatened his popularity. The one thing he’s never been willing to compromise on is defending law enforcement.

In the wake of the Justice Department’s damning report outlining the Ferguson Police Department’s widespread racism, Giuliani opined that Darren Wilson, the officer who shot eighteen-year-old Michael Brown, “should be commended for what he did.” When two NYPD officers were killed in 2014, he blamed it on “four months of propaganda, starting with the president, that everybody should hate the police,” and argued that “police misconduct is a minor part of the problem.”

And after watching Bill de Blasio’s emotional speech about the killing of Eric Garner, in which the current mayor expressed his own fears for his biracial son’s safety, Giuliani remarked that such language “helps to create this atmosphere of protest and sometimes even violence.”

The Vindictive Despot

As mayor, Guiliani didn’t just use his office to defend police and attack shooting victims — he used it against his critics, too.

The New York Times related a story about one citizen who crossed the mayor by informing the New York Daily News about a red-light sting run by the police. Soon after, he was arrested on a thirteen-year-old traffic warrant and had his previous criminal record read out to the press (with a made-up sodomy conviction thrown in). Giuliani publicly mused that given his rap sheet, “maybe he’s dishonest enough to lie about police officers.” The man subsequently suffered a breakdown and was hospitalized.

This wasn’t an isolated incident. A city official pressured New York University’s law school to remove a teacher who had criticized Giuliani’s record on police brutality. Officials sabotaged a nonprofit’s application for a federal housing grant because they’d questioned Giuliani’s record on AIDS. Giuliani had the Transit Authority get rid of New York magazine’s city bus ads because they described the magazine as “possibly the only good thing in New York Rudy hasn’t taken credit for.” (The publication won the ensuing lawsuit, but only after Giuliani twice appealed the decision.)

Giuliani combined this thin-skinned response to criticism with a penchant for secrecy. Desiring strict control over all information released from the mayor’s office, Giuliani banned press conferences outside City Hall, until a federal judge ruled his actions unconstitutional.

When Police Commissioner Bill Bratton had the nerve to praise Giuliani in an interview, he was summoned to Deputy Mayor Peter Powers’ office and threatened with termination. “We will control how these stories go out,” Powers reportedly said. “The mayor has an agenda, and it’s very important that everybody stay on message and that the message come from the mayor.”

One First Amendment lawyer deemed Giuliani “the worst [mayor] in living memory” on matters of free speech and public records. His mayoralty spurred dozens of (successful) lawsuits from news organizations for public information, and advocacy groups were forced to file freedom of information requests for relatively mundane information.

And in an unprecedented move, his associates secretly signed a deal that saw 2,100 boxes worth of documents covering his mayoralty transferred to the Rudolph W. Giuliani Center for Urban Affairs to be copied and archived, before being returned to the city, presumably with all of the original documents intact. (The city council quickly passed a law prohibiting any future mayor from repeating Giuliani’s gambit.)

New York’s City Hall. Mike Steele / Flickr

Giuliani’s attempt to strictly shape perceptions of his administration often involved surrounding himself with questionable yes-men, a tendency that backfired more than once.

The Albert Terranova debacle was the first such episode. Giuliani had initially represented Terranova after he was indicted for defrauding the government. Later, Terranova and his wife acquired a vocational school in Brooklyn, for which Giuliani not only drafted incorporation papers and notarized the application for a license, but also wrote a letter to state officials on Terranova’s behalf calling his management “experienced, dedicated and responsible.”

The school eventually went bankrupt, and years later Terranova pled guilty to stealing tens of thousands of dollars in tuition funds from the school as part of a countrywide, multi-school fraud scheme. In the intervening years, Terranova bought Giuliani a $500 wedding gift and a $250 gift for his newborn son. Unfortunately for Giuliani, the issue flared up ahead of his 1989 mayoral run and dented his image as an honest cop with unimpeachable character.

Giuliani didn’t learn his lesson. Despite his early criticism of “systematic patronage” — accusing New York officials of “turn[ing] over blocks of jobs in agencies to a political leader to fill” — and his promise to do away with it on the campaign trail, he continued the practice and installed associates and their relatives in top posts.

For Giuliani, loyalty was a potential underling’s most prized characteristic. Qualifications were somewhere lower down the list.

The man he chose to run New York’s Housing Development Corporation, the son of a top campaign backer, didn’t even have a background in the field, and took off with $300,000 of the agency’s money. (He was eventually sentenced to prison for embezzlement and possession of child pornography.) Two key appointments failed to obtain federal security clearances. And to top it all off, Giuliani demoted two judges recommended by a judicial screening panel in favor of his own choices, one of which had flunked out of law school twice.

Giuliani, one frustrated former appointee told the Washington Post, “had a blind spot when it came to people he knew well,” resulting in the hiring of “borderline-incompetent people” who drove away the capable ones. “He ran off the professionals because they were difficult to work with,” the former appointee explained. “If they didn’t do things the way he wanted or overshadowed him, he got furious.” Others outright accused him of cronyism.

But Giuliani’s most disastrous appointment by far was Bernard Kerik, a high school dropout and former NYPD narcotics detective who met Giuliani while serving as his driver-cum-bodyguard during the 1993 mayoral campaign. Although Kerik had never even passed a promotional exam, the bond he forged with Giuliani led to an appointment in the Corrections Department, and eventually to a promotion to NYPD commissioner.

After both men had left city government (and started a security consulting firm together), Giuliani recommended that George W. Bush nominate Kerik to be head of the Department of Homeland Security. Kerik’s nomination sank under a hail of scandals.

He had, among other things: not paid taxes on the salary of a nanny who was an undocumented worker, accepted expensive gifts as police commissioner without reporting them, and convinced the owner of a luxury apartment building to allow police and firefighters working at Ground Zero to use his apartments, which he then used to carry out an affair. He was later sentenced to four years in prison after pleading to tax fraud and six other felonies.

“I made a mistake in not clearing him effectively enough,” Giuliani said, in one of the biggest understatements of his career.

Playing the Race Card

It’s impossible to separate Giuliani’s coddling of law enforcement and alacritous use of the bully pulpit to, well, bully his enemies, from the issue of racism.

To be sure, his record on this score isn’t all bad. As US attorney, Giuliani charged two police officers that targeted mostly people of color with false arrests after the Manhattan district attorney declined to charge them. He also rewrote allegedly discriminatory police exams and prosecuted a rental agency accused of discriminating against African Americans. However, these aberrations were few and far between, and came early in Giuliani’s career when he was still burnishing his image as an incorruptible public servant.

By the time 1989 rolled around and Giuliani was campaigning against Dinkins — vying to be the city’s first black mayor — this more conciliatory approach evaporated. Giuliani, twenty-four points behind Dinkins in September 1989, needed something to give him an edge. He appears to have settled on race-baiting.

Giuliani repeatedly tried to present Dinkins as a clone of Jesse Jackson, who was unpopular with many Jewish voters for making antisemitic remarks and previously associating with Louis Farrakhan (who Jackson subsequently disavowed). Giuliani placed an ad in a Yiddish newspaper that was framed as a “personal message to the Jewish people” on Rosh Hashanah, accompanied by a picture of Giuliani with George H. W. Bush and Dinkins with Jackson. (His smear campaign ignored the fact that Dinkins had denounced Farrakhan, possibly risking his own safety.)

Giuliani also accused Dinkins of taking “the weakest position on criminal justice” and said he was “almost always on the permissive side” on crime.

While Dinkins narrowly beat Giuliani in the 1989 election, the former prosecutor spent the intervening years intensifying his attacks. In 1991, he charged that Dinkins “retreats into black victimization,” even though Dinkins had refused to chalk up criticism of himself to racism. “From a cold political calculation, you take the issue of race out of this and I win by 15 to 20 points,” Giuliani told the New York Times in 1993. “You make this a normal American election between an incumbent and a challenger, and I win.”

Joe Schumacher / Flickr

Most notorious, however, was Giuliani’s role in stirring up a racist police riot in September 1992.

The riot began as a ten-thousand-strong, predominantly white rally that included six thousand off-duty officers. They were demonstrating against an all-civilian agency that Dinkins had proposed to investigate police misconduct.

Even before Giuliani rose to speak, officers were carrying signs that had messages like “Mayor, have you hugged your dealer today,” “Dump the washroom attendant,” and “The Mayor’s on crack.” One displayed a racist caricature of Dinkins. Within a couple of hours, the demonstrators had occupied the Brooklyn Bridge, blocking traffic for an hour, and climbed over barricades, jumped on cars, shouted racist epithets, and attacked journalists.

Giuliani received a tidal wave of criticism for delivering a profanity-laden speech that many believed incited the crowd. The New York Post called him an “accomplice” and labeled him “The Human Scream Machine.” Newsday accused him of giving “one of his Young Mussolini speeches.” The Daily News decried him as an “apologist” and said the speech was “shameful.”

Incredibly, Giuliani didn’t let up. In the days after the riot, Giuliani called Dinkins “a mayor who invites riots” and “a hack politician,” and derided him as “anti-police,” blaming him for low police morale. When Dinkins’s deputy mayor compared Giuliani to David Duke, Giuliani accused him of “playing the race card.”

Even Giuliani’s “vulnerability study” — commissioned by his campaign prior to his 1993 run — referred to his actions as an example of “arrogance and self-righteousness” and cautioned him to avoid sounding “strident and shrill.” “Simply put,” it stated, “Dinkins won’t have to work hard . . . painting Giuliani as a racist.”

Despite his promise that “no ethnic, religious, or racial group will escape my care, my concern and my attention,” Giuliani’s ostensible concern mostly fell by the wayside once he was in office.

Under Giuliani, across a host of government departments, the workforce and managerial ranks became less black and more white, reversing a trend that had been moving in the opposite direction. Even worse, his punitive and invasive policing strategy disproportionately affected communities of color, with cases of police misconduct and brutality becoming more prevalent. In Giuliani’s New York, even the deputy mayor — one of his administration’s highest-ranking African Americans — wasn’t safe from being stopped and getting roughed up by the police.

Additional episodes — former Mayor Dinkins’s arrest at a protest over the Diallo killing; the Dorismond shooting — coupled with Giuliani’s refusal to listen to complaints about police misconduct — he belittled and dismissed the suggestions of his own task force about how to reduce tensions between police and residents — accelerated this trend.

One month after Dorismond’s funeral, Giuliani’s approval rating hit a nadir of 37 percent, with a mere 6 percent of black voters saying they supported the job he was doing. In November 2000, the Village Voice referred to him as the “disgraced Republican mayor.”

Freed from the shackles of the mayoralty, Giuliani has become increasingly unrestrained in recent years. After de Blasio spoke about he and his wife “training” their son to be careful when dealing with police, Guiliani commented that “if he wants to train young black men in how to avoid being killed in this city,” he should “spend 90 percent of [his] time talking about the way they’re actually probably going to get killed, which is by another black. To avoid that fact, I think is racist.”

Debating with Georgetown professor Michael Eric Dyson after the Michael Brown shooting, he told Dyson that “white police officers wouldn’t be there if you weren’t killing each other.” It’s not hard to see why Giuliani quickly became one of Trump’s top advisers, given that the president-elect built his campaign on remarks that can barely be classed as dog-whistling.

The Guru of 9/11

For the United States and the world, September 11 was a horrific disaster and a cataclysmic event that sent the world hurtling into a dangerous new direction. But for Giuliani, September 11 was something of a godsend, rescuing his political career from the doldrums.

In addition to his criminal justice policies, a lackluster Senate campaign and a highly publicized affair had conspired to bring down Giuliani’s standing with the public.

The September 11 attacks — and Giuliani’s well-publicized stewardship of the city in their wake — turned him into a hero, an object of admiration for celebrities and world leaders. David Letterman called him “the personification of courage.” Oprah praised his “extraordinary grace under pressure.” French president Jacques Chirac dubbed him “Rudy the Rock.” Time feted him as “Mayor of the World,” named him 2001’s person of the year, and declared he would “be remembered as the greatest mayor in the city’s history.”

By 2006, he was the most popular candidate mulling a run for president. Celebrities like Robert Duvall, Kelsey Grammar, and Adam Sandler — who gave Giuliani a flattering cameo in his 2003 comedy Anger Management lined up in droves to support his 2008 presidential campaign.

The attacks didn’t just give Giuliani’s career a boost. They also gave him one more title to add to his résumé: terrorism expert.

Over the past fifteen years, nearly everyone, it seems — countless journalists, even Giuliani’s political rivals — has been united in assuming that the man who led New York after the attacks has something important to say about terrorism and national security. In making a pitch for his appointment to secretary of state, Giuliani suggested that terrorism and decimating ISIS would be at the top of his agenda.

Yet Giuliani’s actual record on the matter has always been questionable.

In a flattering post-9/11 Time profile, Giuliani told the magazine that unlike other policymakers, he had always understood the danger of a terrorist attack in the city. “I assumed from the time I came into office that New York City would be the subject of a terrorist attack,” he claimed, citing the 1993 World Trade Center bombing. “[W]hile most New Yorkers pushed the memory aside, Giuliani did not,” the profile stated, pointing to his creation of the Office of Emergency Management (OEM).

However, Wayne Barrett and Dan Collins have reported that the OEM took more than six years after the bombing to open, during which time it had next to no budget or staff. And while the OEM carried out ten major drills, none involved an attack on the World Trade Center. The OEM also never developed a plan to deal with a high-rise fire.

In fact, Bratton and a variety of other public officials told Barrett that Giuliani and his team never once asked about terrorism upon his assumption of the mayoralty in 1993, consumed instead by fighting day-to-day crime. Bob Kerrey, the 9/11 commissioner, told the Times that the “preparation for another attack on the World Trade Center was almost zero.”

Giuliani’s administration, it turned out, made a number of fatal mistakes in planning for an attack. The administration opted to put the OEM command center in the World Trade Center itself over the objections of other officials and departments (including the NYPD, which produced a detailed memo in 1998 warning against it). Not only was the center a prime target for an attack, the memo pointed out, but, in its longest section, the memo noted that a large bomb could bring down the building, taking the OEM out of the picture — precisely what happened in the attacks.

Even though communications equipment had malfunctioned during the 1993 bombing, Giuliani declined to replace the radios until eight years later. When he finally did, he gave Motorola a $14 million no-bid contract to supply the new radios, which began having technical problems within a week. The equipment was then recalled, and the city continued using the original malfunctioning radios. On the day of the attacks, 120 firefighters stayed in the North Tower when a police helicopter warned of its collapse.

Giuliani also bears responsibility for the first responders, recovery workers, and others near the site that became fatally ill. After the towers fell, he took jealous control of the recovery operation and kept out federal agencies. In his rash push to get the city up and running as quickly as possible, he unevenly enforced federal requirements for those at the site to wear respirators.

Giuliani’s personal conduct didn’t help either. When he visited Ground Zero, Giuliani elected not to don a respirator, suggesting to the public that it was safe to follow his example. In fact, Giuliani made this explicit. “[The air] may be uncomfortable and it may be offensive — and it is in many ways — but the reality is, it is not dangerous,” Giualini told CNN a month after the attack, in an article that made the case that the polluted air wasn’t a health threat.

Since 2001, Giuliani has used the national platform the attacks afforded him to promote an aggressively neoconservative foreign policy.

“Thank God that George Bush is our president, and thank God that Dick Cheney . . . is our vice president,” Giuliani proclaimed in his 2004 Republican National Convention speech. He went on to compare Bush to Churchill and stated that “in any plan to destroy global terrorism, Saddam Hussein needed to be removed.”

Four years later, this time on the presidential campaign trail, Giuliani called the idea that US foreign policy helps fuel terrorism “absurd.” While he agreed that the United States shouldn’t torture, he expressed doubt that waterboarding qualified and said that banning sleep deprivation was like saying he was “getting tortured running for president.”

Giuliani on the presidential campaign trail in January 2008. Reese Derrenberger / Flickr

Unsurprisingly, Giuliani was the darling of the neocons during his failed run. His supporters included Charles Hill (a former Reagan official who pushed for both the Iraq War and intervention in Syria), Daniel Pipes (who, among other things, advocated a military conflict with Syria in 2000), and Norman Podhoretz (one of neoconservatism’s “founding fathers”). At the time he was Giuliani’s leading adviser, Podhoretz was advocating for the US to bomb Iran.

Giuliani continued beating the same drum after his abortive presidential bid. In 2009, he complained that the Obama administration was drifting away from the idea that the Unites States was “at war” with terror, and believed it was showing “an overconcern with the rights of terrorism.” More recently, he’s (incorrectly) made the case that “anything’s legal” during war, including seizing a country’s oil reserves.

Much of this was somewhat ironic considering that Trump positioned himself as something of a noninterventionist during the campaign, touting his (nonexistent) opposition to the Iraq War and attacking Bush for lying the US into the war. Indeed, former Bush officials and other assorted hawks — including Podhoretzopposed Trump for most of the campaign.

For his part, Giuliani gamely played the role of shape-shifter, defending Trump against neoconservatives’ criticism earlier this year and calling the national security officials opposing him “the people who have been running policy for the last eight or ten years, twelve years.” The American people “say America is headed in the wrong direction. These are the people who headed it in the wrong direction,” he said, forgetting his prior support for exactly the same direction.

A Question of Ethics

At first glance, Giuliani’s early history might seem to indicate his prowess as a “swamp drainer.” After all, this was the US attorney who was dubbed the “modern-day Elliot Ness,” who loathed corruption in all its forms and went after it with a vengeance.

This reputation wasn’t based on nothing. Giuliani prosecuted corrupt politicians and political bosses, and went after Wall Street figures involved in insider trading and other shady dealings. He had three financial executives from Goldman Sachs and Kidder Peabody handcuffed in their offices and arrested.

The Wall Street Journal, dissatisfied with his targeting of financial firms, at one point ranked him “the most dangerous man in America” to appoint as Securities and Exchange Commission chairman, after his name was floated for the position. “One strain seen in much of Giuliani’s work,” the Christian Science Monitor wrote the same year, “is a concern for ethics.”

Giulani did much to play up his probity. In his Christian Science Monitor profile, he expressed his disdain for those who grew up “with all the advantages” and turn to white-collar crime, spoke of his disgust for the prevalence of bribery in New York, and rued the fact that “we’re going to have to drag people kicking and screaming into making a lot of the reforms and changes [needed in the political system].”

He told Vanity Fair that, contrary to accusations that arrested Wall Street executives had been handled unnecessarily roughly, they had been treated like any other criminals — the only difference being that “they’re rich and powerful and have the ability to affect public relations.”

In a 1986 op-ed for the Times titled “How to return ethics to New York,” Giuliani warned that government spending was permeated by graft. “[A]ll opportunities for private profit from public employment,” he argued, “should be thoroughly eliminated.” He recommended, among other things, banning the holding of private investments by public officials that would be affected by government action, prohibiting public officials from conducting private business, and requiring appointees to put their investments in blind trusts.

It was the kind of populist, anti-elite rhetoric that might have resonated with voters this year. Unfortunately, Giualini has also consistently shown he’s more than happy to jump into bed with the same interests he’s sometimes demonized when angling for public office.

Rudy Giuliani at a Trump rally in Phoenix on August 31, 2016. Gage Skidmore / Flickr

After losing the 1989 election to Dinkins, Giuliani immediately turned his back on his reputation as the scourge of Wall Street by becoming a corporate lawyer. He made $500,000 a year as a partner with the law firm Anderson Kill Olick & Oshinsky.

Prosecutors chuckled at the irony of a man who had made his name arguing for an expansive application of the RICO law suddenly making his living by winning dismissals of RICO actions against his clients. AT&T’s vice president told the Wall Street Journal they had hired Giuliani specifically for his “expertise in the RICO area.”

For all Giuliani’s talk of creating a more ethical government — and his complaints that New York under Dinkins’ predecessor, Mayor Ed Koch, had become “a city that could be purchased” — his actions belied his rhetoric.

In 1997, Giuliani was slapped with the biggest fine in the history of the New York City Campaign Finance Board when it surfaced that his campaign had violated contribution limits 157 times. Many of the donations in question came from corporations who were doing, or planning to do, business with his administration.

While he made sure to stay within the letter of the law in subsequent years, Giuliani continued to take money from businesses doing deals with the city, raising more than $1.2 million in 1999 alone. (His spokesperson at the time claimed the donations had no influence on him.) After a Manhattan Supreme Court Justice ruled in 2000 that a $104 million city contract had been corruptly awarded, Giuliani dismissed it as a “jerky decision” from a “Democratic judge.”

A Corporation’s Best Friend

Giuliani’s willingness to mix money and politics — and trade off his name — went into overdrive once he left the mayoralty. In 2002, “America’s mayor” founded the consulting firm Giuliani Partners.

The firm’s office was located in Five Times Square, a high rise owned by Ernst & Young, which had received a $20 million incentive package from the Giuliani administration to build it. The accounting firm also happened to have helped the former mayor get Giuliani Partners off the ground. Later, Giuliani Partners forged a “strategic alliance” with Bear Stearns for private equity investment, six years after Giuliani awarded the bank a $75 million tax incentive.

Once he rejoined the private sector, Giuliani’s former reputation as the policeman of Wall Street proved no obstacle for his new role as its ardent champion. In one embarrassing instance in 2002, Giuliani personally phoned then–New York attorney general Eliot Spitzer to try to persuade him not to go public with allegations that investment bank Merrill Lynch had knowingly promoted unsound stocks to cozy up with the companies. At the time, Giuliani was receiving $200 an hour to represent the bank. (Later, when Giuliani launched his presidential campaign, many Wall Street banks returned the favor and supported their former foe.)

The same year, Purdue Pharma, the makers of OxyContin, took advantage of Giuliani’s star power and hired him to help them block impending restrictions on the drug, which the DEA was investigating. Giuliani — who was also helping raise money for a DEA museum — personally met with the head of the DEA and successfully persuaded her that the restrictions were unnecessary. If that conflict of interest wasn’t enough, Giuliani’s security consulting firm, Giuliani-Kerik, was also being paid $1.1 million to reorganize a task force that was partly in charge of preventing the illegal use of OxyContin.

In his new private sector endeavors, Giuliani rarely missed an opportunity to exploit the September 11 attacks and warn of purported national security threats. When lobbying to prevent cheaper prescription drugs from being imported from Canada, he testified before Senate committees and produced a report that claimed doing so “risks undermining security and safety” at a time when “the nation [is tightening] its borders against possible future terrorist attacks.”

He promoted wireless-phone company Nextel as crucial to national security, sometimes leaving out that they were a client and at one point claiming that the “chaotic scene at Ground Zero . . . might have been worse” without Nextel’s equipment. This despite the fact that Nextel phones had a well-earned reputation among New York police and firefighters for getting jammed. Nevertheless, when Nextel’s stock later soared before being bought out by Sprint, Giuliani Partners pocketed around $15 million.

Giuliani’s private sector escapades took him around the world. He jumped from country to country, spreading his “zero-tolerance,” crime-busting wisdom, for a price. He was hired to advise a Peruvian presidential candidate in 2011, counseling him to, among other things, build more jails. The city of Rio de Janeiro brought him on as a security consultant ahead of the 2016 Olympics, and soon implemented a range of draconian policies. Mexico City paid Giuliani Partners $4.3 million to help fix the city’s crime problem, with little to show for it.

Incredibly, even while Giuliani was using his government connections and post-9/11 luster to enrich himself and his clients, he never registered as a lobbyist. Giuliani also continued working part time for Giuliani Partners when he ran for president in 2008, and took six-figure speaking fees (complete with a lavish contract that mandated opulent hotel rooms and jets that were Gulfstream IV or bigger) right up until he announced his campaign.

And Giuliani Partners wasn’t even the extent of it. In 2005, Giuliani joined the law firm Bracewell & Patterson, which promptly changed its name to Bracewell & Giuliani. The firm’s managing partner was a “top-shelf Bush fundraiser,” according to the New York Times, and its employees ended up giving hundreds of thousands of dollars to Giuliani’s 2008 campaign.

In 2007, 175 companies were listed as law and lobbying clients for the firm, including NewsCorp, AOL Time Warner, Apple, Bank of America, GE, and Bechtel. It also represented a medley of high-profile polluters, including Chevron/Texaco, Shell Oil, and Citgo.

Many of the companies are past, present, and/or potentially future recipients of government contracts, particularly in the defense sector, such as the Airborne Tactical Advantage Company, a supplier of tactical aircraft and various services for the US military that has received over $200 million worth of government contracts over the past eight years.

For one year, Bracewell & Giuliani also represented AKAL Security, which describes itself as “the largest provider of contract Judicial Security services.” It also provides security for state and local government agencies as well as “critical federal government facilities,”  including immigration detention centers.

Not content to consort with odious domestic figures, Bracewell & Giuliani branched out to international villains. As mayor, Giuliani famously rejected a $10 million donation from Saudi Prince Alwaleed bin Talal that was intended to go to the September 11 recovery effort — the then-mayor was upset at the prince’s claim that US policies contributed to the attacks. But Giuliani appears to have had no qualms with Bracewell & Giuliani taking Saudi Arabia on as a client, despite the monarchist government’s promotion of Wahhabism, a reactionary branch of Islam.

In January of this year, Giuliani left Bracewell (as it’s now known) and joined Greenberg Traurig, a global law firm based in Miami that embodies the revolving door between government and business.

As the firm’s website boasts, its Chicago office alone “includes a former United States Attorney, five former Assistant United States Attorneys and two former Cook County Assistant State’s Attorneys,” as well as “a former supervisor of the Financial Crime and Government Fraud Unit in the Cook County State’s Attorney’s Office, a former senior official of the United States Department of Health and Human Services, and a former White House Chief of Staff and Unites States Secretary of Transportation.”

And its clients? In the past, pharmaceutical giant Amgen, Comcast, General Motors, Hyundai, and several tobacco companies. And currently: a subsidiary of private prison operator Corrections Corporations of America, the chemical and pharmaceutical company Bayer, and the Business Roundtable, a trade association of American CEOs that supported the Trans Pacific Partnership and wants to cut Medicare and Social Security.

A far cry from Giuliani’s ostensible anti-corporate roots indeed.

Goodbye Rudy?

Giuliani’s entire career has been one long, ambitious climb to power, one rung at a time. Now, it appears to have ended — or at the very least, been placed on hold.

His failure to secure the secretary of state post, and his decision not to seek any other position in the Trump administration, should be met with a nationwide sigh of relief (even if he’s reportedly been bested by Rex Tillerson, the Exxon Mobil CEO whose record is filled with black marks roughly the shade of crude oil).

Whether trampling basic civil liberties as a prosecutor, fiercely defending abusive authorities while cracking down on the most marginalized as mayor, or using his office to retaliate against political enemies and critics, Giuliani has spent decades putting into practice some of the worst tendencies people fear from a President Trump. And let’s not forget, he was as knee-deep in fossil fuels and corporate money as Tillerson is.

At the same time, we shouldn’t be too quick to pour one out for Giuliani’s political career. Giuliani has stated that he will continue to act as an unofficial adviser to Trump, similar to his role in the campaign, and pledged to keep “helping the President-elect in any way he deems necessary and appropriate” from the private sector.

And as for Trump? He “can see an important place for him in the administration at a later date.” If we’ve learned one thing from Giuliani’s career, it’s that he loves a comeback.