Donald Trump's most loyal surrogate, Rudy Giuliani, is reported to be in line for high-ranking positions within the administration, specifically secretary of state or attorney general. And many of his New York City legal rivals, who battled Giuliani during his time as mayor, have reservations what his potential appointment could mean for civil liberties.
“The most serious thing is how thin-skinned he is — and we saw that in a First Amendment context — he undermined, trashed, ignored the First Amendment,” said attorney Norman Siegel, the former executive director of the New York Civil Liberties Union (NYCLU) during Giuliani’s years as mayor.
Richard Emery, a New York civil rights attorney who has known Giuliani since the 1970s, called him “a very accomplished, experienced, sophisticated public servant and criminal prosecutor. Extremely vocal and aggressive.”
Emery suspects that if Giuliani served as Trump’s attorney general, we’d see a “dramatic retrenchment on civil rights and civil liberties.”
“For civil rights, he’s a serious threat,” Emery said. “I have a begrudging respect for him. But I don’t like the program.”
Spokespeople for Giuliani and for Trump's transition team didn't immediately return BuzzFeed News' requests for comment.
During Giuliani's mayoral years, the NYCLU was directly involved in 23 cases involving First Amendment issues against his administration. Of those 23 cases, the NYCLU came out on top — either by court order or settlement — in 19 of them.
“We brought more cases and won more cases against him than Mayor Koch or Dinkins,” Siegel said.
As mayor, Giuliani found himself fighting in court on First Amendment issues with a variety of different opponents, including public employees, police, protesters — and a city museum.
In 1998, Giuliani went up against activist groups wishing to hold big rallies on the steps of City Hall when his administration adopted a policy that limited groups to 25 or 50 people. “He thought they were his steps,” Siegel said.
At the time, Giuliani said the decision stemmed from safety concerns following the US Embassy bombings in Africa in 1997. “They ostensibly did that in the name of terrorism,” said attorney Chris Dunn, who litigated many of the NYCLU’s First Amendment cases against the Giuliani administration.
In July 1998, the civil rights group Housing Works sued the City to allow them to hold a big rally on the steps for World AIDS Day. In court, an NYPD official invoked the policy, no exceptions.
Then, in October 1998, Giuliani sponsored and attended a rally for the New York Yankees after they won the World Series. About 5,000 people gathered on and around the City Hall steps. After that, the administration adopted a new policy allowing big events to take place at City Hall if they had "extraordinary public interest" — such as a sports team’s championship.
Housing Works was able to obtain a temporary clearance to hold a rally in December 1998 for Worlds AIDS Day with about 200 people. Giuliani's administration reportedly enlisted a hundred NYPD officers — including sharpshooters on the rooftops around City Hall — to police the rally.
Giuliani continued to hold big events. In November 1998, Giuliani and the City’s administration held a rally for US astronaut John Glenn and distributed 3,000 tickets. The following year, when the Yankees repeated as World Series champions, Giuliani threw them another rally.
In the end, the court sided with Housing Works. Two years later, in 2000, Judge Harold Baer ruled that City Hall’s event policy was "not narrowly tailored to a significant government interest" and granted an injunction against limiting the size of public gatherings.
Giuliani’s deference to certain groups over others was addressed in Judge Baer’s ruling: “The City's recent sponsorship of a celebration for the Yankees after their 1999 World Series victory in October illustrates that the defendants' Rules are made to apply only to those events which the City has chosen not to sponsor.”
On several occasions, Giuliani clashed with NYPD officers who wanted to openly disagree with the force. In one case, a black NYPD officer, Yvette Walton, sued the NYPD and city, claiming she was fired in 1999 for speaking out in the aftermath of the Amadou Diallo shooting by four white officers in the NYPD’s Street Crime Unit, saying that the unit engaged in racial profiling.
A judge ruled in 2000 that Walton was fired as retaliation for what she said. But after the ruling, Giuliani said publicly that the judge had made a mistake.
"That decision is incorrect because I went over that decision with [the police commissioner] and I think the judge has made a mistake," Giuliani said. "I think the police commissioner fired her for entirely different reasons, and the reasons appear to be justified by the record including the absences, an altercation with a commanding officer and things that are left out of the decision.”
Giuliani’s administration vowed to appeal the case, but in the end it settled with Walton, paying her more than $300,000 in damages and allowing her to retire with full benefits.
In another memorable free speech case from the '90’s, Giuliani attempted to cut millions in financing to Brooklyn Museum over the exhibition Sensation by British artists Chris Ofili and Damien Hirst, which he called “sick stuff.”
The exhibition included a painting of the Virgin Mary with elephant dung — a trademark of Ofili’s work — smeared across her breast, which Giuliani said offended him as a Catholic.
"You don't have a right to government subsidy for desecrating somebody else's religion," Giuliani said. "The idea of having so-called works of art in which people are throwing elephant dung at a picture of the Virgin Mary is sick."
The Brooklyn Museum challenged Giuliani in federal court over his threat to cut its funding and the NYCLU joined the case. In the end, a district judge ruled that the administration’s actions violated the First Amendment.
The city appealed and at oral arguments, Leonard Koerner, the chief appeals attorney for Giuliani’s city law department, told the panel of judges, "we want to terminate the [museum’s] lease and maybe negotiate with a new group ... appropriate for schoolchildren."
One of the judges hearing the appeal, Jon Newman, responded, "Is every book in the New York Public Library appropriate for schoolchildren?"
"No,” Koerner said.
"Are they next?” Newman shot back, getting a laugh from the courtroom.
In April 2000, the Giuliani administration withdrew its appeal before the judges could rule and agreed to pay the museum a substantial settlement.
“That was purely a morals crusade on the part of Giuliani, if that gives you a flavor or what’s to come,” Dunn told BuzzFeed News.
More recently, Giuliani has been vocal about the demonstrations following Trump's election.
During an appearance this week at the Wall Street Journal’s CEO Council, Giuliani referred to the protesters demonstrating in New York City after the election as “goons and thugs that are in my city, that are taking over streets, and are yelling and screaming at Donald Trump.”
“Undercutting all this, it shows an utter lack of respect for the First Amendment,” Dunn said. “The common thread: Giuliani is completely prepared to run roughshod” over it.