Former New York mayor Rudy Giuliani told reporters on Friday that his advice to President-elect Donald Trump is "out of great loyalty" and has "no expectation" about his role in Trump's administration. (Victoria Walker/The Washington Post)

Among the names being tossed around for Donald Trump’s attorney general is Rudy Giuliani, a politician that the journalist Jimmy Breslin once called “a small man in search of a balcony.” Of course, Giuliani’s name isn’t a surprise. The former New York mayor — who once said that “freedom is about the willingness of every single human being to cede to lawful authority a great deal of discretion about what you do” — has been a Trump adviser and surrogate for months. He’s actively lobbying for the Justice Department post, but he has also been mentioned as a possibility to head up the Department of Homeland Security.

It seems likely that Trump’s election is the end of criminal-justice reform at the federal level. Given his campaign rhetoric, and Trump’s endorsement by nearly every law enforcement agency in the country, I doubt we’ll see any more damning reports on police abuse from the Justice Department’s Civil Rights Division. But Giuliani at Justice is an especially troubling proposition. This is a man whose career has been marked by prosecutorial excesses, knee-jerk defenses of abusive cops and an affinity for using the power of his political offices to get vengeance on his enemies.

Let’s look first at his tenure as the mayor of New York. Giuliani has always been a stalwart defender of abusive cops. In 2000, two undercover New York Police Department detectives shot and killed 26-year-old Patrick Dorismond. The detectives asked Dorismond if he knew where they could find some pot. Dorismond, no pot dealer, was offended at the question, and a scuffle broke out. One of the officers pulled a gun. The detectives claim Dorismond tried to grab it. After the incident, Giuliani released Dorismond’s juvenile record, which by law was supposed to remain sealed. Citing Dorismond’s record as a minor, Giuliani said the dead man was “no altar boy.” (Actually, Dorismond had been an altar boy.) The city eventually paid $2.25 million to Dorismond’s family. The detective was cleared. Giuliani defended the release of Dorismond’s juvenile records by claiming the man had no right to privacy after death. Giuliani also defended the officers who shot Amadou Diallo 19 times after he pulled a wallet out of his jacket to show them his ID.

Former New York City Mayor Rudy Giuliani (R) is a big fan of Donald Trump – and he said some strange things while campaigning for the Republican nominee. (Peter Stevenson/The Washington Post)

Giuliani of course was also the mayoral architect of “Stop & Frisk,” and still widely touts its success, despite the fact that murders in New York have continued to decline since the NYPD largely stopped the practice. Giuliani also stepped up street-level enforcement of the drug laws, often with the use of SWAT tactics and no-knock raids. In 1990s New York, raid teams kicked down doors left and right, often based on little more than tips from shady informants. Despite increasing complaints and media reports of brutality, excessive force, and raids on innocent people and families throughout the decade, the Giuliani administration did nothing. By the time Alberta Spruill — an innocent, 57-year-old woman — was killed in a mistaken raid in 2003, the NYPD was conducting 450 such raids per month. Police Commissioner Ray Kelly said after Spruill’s death that about 10 percent were on the wrong address. That 45 or so New York residences were wrongly raided each month was apparently an acceptable figure. But Kelly also conceded that the number could be higher, because the department didn’t really keep track of how often they mistakenly waged volatile terrifying raids on innocent people. (Today, the NYPD is one of the more restrained big-city police departments when it comes to such tactics, although there are still some problems.)

Under President Obama, at least some parts of the Justice Department tried to encourage less militaristic, less reactionary, more community-oriented policing. That will likely end no matter whom Trump puts at DOJ. But it would certainly end under Giuliani.

Giuliani  the mayor was also hostile to the First Amendment. He waged war on a Brooklyn art museum because it displayed a painting he found offensive. He later tried to assemble a “decency task force” to seek out art at public museums for possible censorship. Giuliani often boasts of his crackdowns on pornography. Earlier this year, Trump vowed to do the same. (He has also added famous anti-porn crusader Ed Meese to his transition team.) Should he head up the Justice Department, we can probably expect Giuliani to invest considerable resources toward eradicating Internet pornography. That will never happen, of course. But they could certainly make examples of a lot of people. Giuliani also used zoning laws and quality-of-life ordinances to crack down on protests, street vendors and advertisements he found distasteful (or, in many cases, were critical of him). He took New York magazine to court (and lost) over a bus ad the magazine took out because it mentioned his name.

In giving Giuliani a lifetime “muzzle award” for his hostility to free speech, the Thomas Jefferson Center for the Protection of Free Expression wrote, “He has stifled speech and press to so unprecedented a degree, and in so many and varied forms, that simply keeping up with the city’s censorious activity has proved a challenge for defenders of free expression.” First Amendment attorney Floyd Abrams called Giuliani “the single most consistent opponent of First Amendment rights in living memory.” In a 2007 profile for Washington Monthly, Rachel Morris pointed out that as mayor Giuliani lost 35 First Amendment lawsuits.

As the New York Times reported in 2008, Giuliani was also an incredibly vindictive mayor. The paper likened him to a boxer, writing that “he made the vengeful roundhouse an instrument of government, clipping anyone who crossed him.” One man confronted Giuliani during a radio show about a red light sting in his neighborhood. When Giuliani didn’t respond, the man went to the New York Daily News. The same morning the article ran, NYPD cops showed up at the man’s door to arrest him on a 13-year-old traffic warrant. The NYPD then released the man’s decades-old record, despite the fact that it was supposed to be sealed. An NYPD spokesman also falsely claimed the man had been convicted of “sodomy.”

The Times article lays out how Giuliani used licensing bureaus, housing codes and other city government infrastructure to punish whistleblowers, critics, detractors and disloyalists. He not only tried to get his political opponents fired; when he heard they were being considered for other positions, he’d call the potential new employers to pressure them to look elsewhere. Giuliani’s vindictiveness could be incredibly petty.

After AIDS activists with Housing Works loudly challenged the mayor, city officials sabotaged the group’s application for a federal housing grant. A caseworker who spoke of missteps in the death of a child was fired. After unidentified city workers complained of pressure to hand contracts to Giuliani-favored organizations, investigators examined not the charges but the identity of the leakers.

“There were constant loyalty tests: ‘Will you shoot your brother?’ ” said Marilyn Gelber, who served as environmental commissioner under Mr. Giuliani. “People were marked for destruction for disloyal jokes.”

Mr. Giuliani paid careful attention to the art of political payback. When former Mayors Edward I. Koch and David N. Dinkins spoke publicly of Mr. Giuliani’s foibles, mayoral aides removed their official portraits from the ceremonial Blue Room at City Hall.

When civil rights attorney and New York University law professor Joel Berger wrote a New York Times op-ed criticizing Giuliani in 1997, the mayor’s aides called NYU and threatened to cancel an apprenticeship program the city ran with NYU unless the school fired Berger from the course he was teaching.

Donald Trump is of course famously vindictive himself. He has banished reporters from publications who criticize him. He has openly suggested altering the libel laws to make it easier to sue journalists who write things he doesn’t like. He sued author Tim O’Brien for $5 billion because in his biography of Trump, O’Brien suggested that the now president-elect was merely worth $150-$200 million, not the $9 billion Trump claimed. Trump knew the lawsuit was a loser. He just wanted O’Brien to suffer.

Trump’s campaign aides have already declared that he’s keeping an enemies list, and that he and they fantasize about retribution. Giuliani had no qualms about using his power as the mayor of New York to settle personal and political grievances. Now imagine Giuliani settling scores — his and Trump’s — with the vast resources of the Justice Department at his disposal. He’ll have the FBI. He’ll have an army of U.S. attorneys. And he’ll have virtually unlimited funding.

As noted, Giuliani was quick to release the sealed criminal records of police critics and victims of police shootings and brutality. He wasn’t as forthcoming with his own records. Just before he left City Hall, he cut a shady deal with the city that transferred all of his records to his own private company, so only he could control who accessed them.

For all Giuliani’s criticism of Black Lives Matter protests, the prospective next attorney general launched his political career by inciting an actual violent protest. When he ran for mayor in 1992, Giuliani spoke to a raucous crowd of white cops protesting then-mayor David Dinkins’s proposal for a civilian review board. From the New York Times:

Hundreds of white off-duty officers drank heavily, and a few waved signs like “Dump the Washroom Attendant,” a reference to Mr. Dinkins. A block away from City Hall, Mr. Giuliani gave a fiery address, twice calling Mr. Dinkins’s proposal “bulls–t.” The crowd cheered. Mr. Giuliani was jubilant.

“If you’re acculturated to like cops, you don’t necessarily see 10,000 white guys who don’t vote in the city, don’t write political checks and love you for the wrong reason,” an aide said. He spoke on condition of anonymity because he is working with the Giuliani presidential campaign.

Mr. Dinkins has not forgotten that sea of angry cops. “Rudy was out there inciting white cops to riot,” Mr. Dinkins said in a recent interview . . .

Incite them he did. Nearly 10,000 cops rampaged through the city. Nat Hentoff and Nick Hentoff recently recalled the riot in a piece published at the Cato Institute:

Reporters and innocent bystanders were violently assaulted by the mob as thousands of dollars in private property was destroyed in multiple acts of vandalism. The protesters stormed up the steps of City Hall, occupying the building. They then streamed onto the Brooklyn Bridge, where they blocked traffic in both directions, jumping on the cars of trapped, terrified motorists. Many of the protestors were carrying guns and openly drinking alcohol.

Blocking traffic. Occupying public buildings. Sounds familiar, no? And yet Giuliani never condemned the rioters. From the New York Times: 

The Giuliani campaign later conducted a “vulnerability study” to identify their candidate’s weaknesses in 1993. This study, obtained by Wayne Barrett, author of “Rudy!” — an investigative biography — offers an unsparing critique: “Giuliani’s shrieking performance at the cop rally may be his greatest political liability this year. Giuliani has yet to admonish those who attacked the mayor with racist code words on signs and banners. Why not?”

Giuliani later ordered the report destroyed.

It’s hard to think of a politician more punitive than Giuliani. As a federal prosecutor, he was credited for inventing the “perp walk,” the practice of parading arrestees before television cameras that prosecutors have notified ahead of time. He made a name for himself with high-profile prosecutions of Wall Street traders and mob bosses, but on more than a few occasions, Giuliani had to drop the charges against suspects he perp-walked. In others, the charges were later dismissed by an appellate court. Perhaps his most famous prosecution was of “junk bond king” Michael Milken. But as William L. Anderson explains in great detail here, in doing so Giuliani pioneered abusive prosecutorial practices like the expansive application of racketeering and conspiracy laws, and the seizing of all of a suspect’s assets before trial. Both are now common, and not just in cases against wealthy Wall Street barons. Conspiracy is now a tool prosecutors use to rope in the girlfriends and relatives of suspected drug dealers, or to connect unconnected events into criminal conspiracies that bring mandatory minimum prison sentences. It has led to some serious miscarriages of justice.  In 2014, the U.S. Supreme Court (inexplicably) upheld the government’s power to seize defendants’ assets before trial, thereby denying them the ability to hire good legal representation.

As Dan Baum documented in his book “Smoke and Mirrors,” during his time at DOJ in the 1980s Giuliani also helped expand the scope and reach of civil-asset forfeiture laws more generally. As mayor of New York, he instructed city officials to seize the cars of first-time drunk-driving suspects. Even if the suspects were acquitted, under Giuliani’s proposal, they’d have to go to court (plus hire an attorney, pay court costs, etc.) to win back their automobiles.

It’s probably safe to say that under Giuliani, the Justice Department would roll back the modest civil-asset forfeiture reforms implemented during the Obama administration. We’d also likely see even less effort to discipline wayward federal prosecutors and a big push to expand prosecutorial power. As a federal prosecutor, Giuliani was also known for prosecuting low-level drug crimes as federal cases.

As Kevin Baker pointed out in a profile for Politico a few months ago, Giuliani wasn’t always the politician he is today. He seems to have grown more authoritarian as he has sought and accumulated power.He voted for George McGovern in 1972.  “He only became a Republican after he began to get all those jobs from them,” Baker quotes Giuliani’s mother saying in 1988. The first job was with the Nixon-Ford Justice Department in the mid-1970s. Giuliani then worked in the private sector during the Carter administration. When Ronald Reagan was elected, he was offered the number three position at Justice. He accepted, but later requested an appointment to be U.S. attorney for the Southern District of New York so he could litigate — and make a name for himself.

But even after a decade as a federal prosecutor, Giuliani’s politics were well to the left of where they are now. In a 1989 profile, New York magazine wrote of Giuliani, “He is perhaps the only white politician in town who draws a positive emotional response — hugs and cheers — in Harlem.” That of course would quickly change after he was elected mayor in 1993.

Yet after his two terms as mayor, Giuliani’s politics were well to the left of much of the GOP, especially on cultural issues such as gay rights and abortion. When he ran for the GOP nomination in 2008, Giuliani lurched to the right, not on taxes or regulation, but by boasting about his efforts to censor art and combat pornography while he was mayor. He also tried to compensate for his cultural liberalism by doubling down on crime and national security issues, running on his longtime support for cops and his record as a prosecutor, as well as support for torturing terrorism suspects, the detention of American citizens without trial and other war-on-terror policies. It was all enough for the the American Conservative — obviously no liberal rag — to portray Giuliani as a fascist on its cover.

Perhaps no issue illustrates how Giuliani’s authoritarianism grows as he seeks higher office than immigration. As Jelani Cobb recently pointed out at the New Yorker, during his tenure as mayor, Giuliani was staunchly pro-immigrant. Recall that during the 2007 campaign, Mitt Romney accused Giuliani of running a “sanctuary city” in the 1990s. (He was right.) As mayor, Giuliani also chastised anti-immigration demagogues like former California Gov. Pete Wilson. Cole cites this remarkable quote Giuliani gave in 1996: “The anti-immigration issue that’s now sweeping the country in my view is no different than the movements that swept the country in the past. You look back at the Chinese Exclusionary Act, or the Know-Nothing movement—these were movements that encouraged Americans to fear foreigners, to fear something that is different, and to stop immigration.” (There is one exception to his early record on immigration. As a Justice Department official in the early 1980s, Giuliani fought the asylum claims of 2,100 Haitian refugees arguing, as the New York Times reported, that “repression in Haiti ‘simply does not exist now’ and that refugees had nothing to fear from the Government of Jean-Claude Duvalier.” The Haitian dictator of course tortured and murdered thousands of his own citizens, and sold the body parts of some of his victims on the black market.)

By the time he ran for president in 2008, Giuliani was talking about border fences and national ID cards. But even then, he still opposed mass deportation and supported a path to citizenship for undocumented people currently in the United States.

Today, he’s lobbying to be the chief law enforcement officer for a president-elect who wants to immediately deport 2 to 3 million undocumented people, and has at various times promised to deport all 12 million. Trump of course also famously promised to ban all Muslims from entering the country. Giuliani initially rejected the plan in December, but in May Trump suggested Giuliani as someone who might head up his task force to hash out his plan for Muslim immigrants.  (Today as a Trump surrogate, Giuliani boasts that as mayor, he sent police officers to infiltrate and spy on city mosques and has suggested “tagging” people on the terror watch list with GPS devices.)

If Giuliani’s authoritarianism does indeed grow as he seeks and collects political power — and there’s ample evidence that it does — imagine what he’ll do if given most powerful position of his life.