Inside the dramatic departure of New York City Hall's top lawyer

NEW YORK — City Hall remains without a permanent top lawyer, more than four weeks since Mayor Eric Adams and his aides pushed out their corporation counsel.

Now, as the deadline looms for Adams to submit his preferred replacement to a restive City Council for consideration, new details have emerged about the mounting tension that ultimately led to the resignation of Sylvia Hinds-Radix.

Hinds-Radix entered the prestigious, $253,000-a-year job as a politically connected judge from Adams’ home borough of Brooklyn. She left the post two and a half years later amid a series of disagreements with the mayor’s office — among them her resistance to defending a top Adams aide facing sexual harassment lawsuits and clashes over asylum-seeker litigation, a POLITICO review has found.

Timothy Pearson — a former NYPD inspector with a plum salary and nebulous job duties — was accused of sexual harassment in March . Court papers outline how he allegedly touched a subordinate, made unwanted advances toward her and then derailed her career when she resisted his advances.

Pearson leads a clandestine mayoral unit closely tied to the NYPD that is focused on monitoring service delivery across city agencies. The division, the Mayor’s Office of Municipal Services Assessment, is housed in a City Hall-adjacent building where the incidents allegedly took place.

In the wake of the suit, the mayor’s office defended Pearson and indicated it wanted the Law Department to represent him — a move that would absolve the mayor's old friend of a mountainous legal bill if he were unable to get representation from a law enforcement union. Three people with knowledge of the situation, who were granted anonymity to discuss internal City Hall dynamics, said Hinds-Radix resisted.

When city officials are sued in civil cases and the allegations relate to their job, state laws entitle them to representation from the Law Department. There is, however, room for interpretation within that framework, which is why the city typically conducts an internal probe before deciding whether to take a case, according to a former government official versed in the city’s legal practices.

If municipal lawyers discover evidence suggesting an employee did in fact run afoul of workplace rules, the city is prohibited from representing that employee. And when a conflict of interest arises, the administration will foot the bill for outside counsel.

In the case of Pearson, Hinds-Radix lost her bid not to represent him. And because the Law Department had an unrelated conflict of interest with the plaintiff, the city hired the law firm Wilson Elser to represent the administration along with Pearson and a top NYPD official, court documents show.

John Scola, the attorney representing Pearson’s accuser, said he was first contacted April 15 by Wilson Elser, meaning the decision to retain lawyers for Pearson was likely made following the first accusation against the Adams confidante. Since then, two related suits have been filed.

Hinds-Radix did not return requests for comment, but she addressed the lawsuit at a March press briefing.

“This is a new case with multiple individuals and different entities,” she said in response to a question about whether the city would represent Pearson. She went on to cite local law requiring the city "conduct representation interviews" to determine its course of action.

City Hall spokesperson Liz Garcia pointed to those comments, saying proper procedure was followed. She disputed there was any disagreement over the final decision.

The Pearson incident marked one of the latest dustups between the mayor’s office and Hinds-Radix, but tensions had been building since the beginning of the administration, according to two additional people who spoke with POLITICO on the condition of anonymity.

In the spring of 2022, just months after Adams took office, an influx of migrants from the southern border began to stream into New York City by bus, swelling the municipal shelter system and creating novel legal questions around the city's response.

The two people who spoke with POLITICO said a marked difference in style between the mayor’s office and Hinds-Radix became readily apparent: City Hall’s inner circle wanted more nimble decisionmaking — including on the city’s efforts to dilute decades-old rules that guaranteed permanent shelter to migrants. Hinds-Radix was unwilling to bend, they said.

“You have to make fast decisions and synthesize legal precedents and economic issues quickly,” one of the people said in an interview. “To do all that, you can’t have lawyers sitting on things.”

Hinds-Radix, referred to as simply “the judge” by people inside and outside City Hall, was known as a plain-spoken operator within government. However, in the eyes of the mayor’s team, she walled herself off too quickly and completely within the vast Law Department.

And while Hinds-Radix formally resigned at the end of June, the drama didn't end there.

The appointment of her replacement — white-shoe attorney and former Giuliani deputy mayor Randy Mastro — has stalled amid pushback within the City Council.

As a result, the Law Department is now being led on an interim basis by Hinds-Radix’s former second in command, which stands to hobble the government’s legal arm at a time when the city is navigating complex matters in the courts.

“Over a few weeks [an interim leader] is nothing. But over months, the agency loses effectiveness because the boss is not empowered to make really important decisions,” John Kaehny of government reform group Reinvent Albany said in an interview.

Kaehny cited decisions about both personnel and policy that are more difficult to enforce without the imprimatur of the mayor. And the Law Department could easily be without a permanent leader through much of the summer.

Hinds-Radix has already been gone a month, and city rules allow Adams until the end of July to formally nominate a replacement. At that point, lawmakers have another 30 days to cast a vote under a 2019 law giving them veto power over the mayor’s pick.

Wrangling over Mastro had ebbed in recent weeks as budget negotiations took prominence in City Hall. But with a $112.4 billion deal in place as of Sunday, the mayor’s push to install his pick is set to begin anew.

"We're working in partnership with the Council to see how things can manifest," Chief Adviser Ingrid Lewis-Martin said at a Tuesday press briefing. "It hasn't changed. We've been in a good place with them, contrary to what the news has been reporting. We needed to get past the budget cycle."

The nomination process has been made more tumultuous by the messy departure of Hinds-Radix — whose short tenure was an aberration at the normally staid Law Department.

Since a charter-mandated overhaul of city government in 1989, every corporation counsel appointed at the outset of an administration has stayed for at least a full term, with one exception. And while the initial head of the Law Department under former Mayor David Dinkins stayed for less than two years, his exit was mutually agreed upon, and City Hall had an immediate succession plan ready.

For Hinds-Radix, signs of City Hall’s displeasure were clear even before an April report in The New York Times detailed City Hall's efforts to court Mastro.

Officials close to the mayor signaled to the former state Supreme Court judge six months ago they wanted her to go, according to one of the people who spoke with POLITICO, who added that the overtures were met with resistance. And a week before the Mastro news broke, the mayor’s team essentially bypassed Hinds-Radix altogether.

That month, Adams was accused of sexual harassment by a former colleague in the Transit Police, a separate law enforcement arm that was later consolidated with the NYPD. According to a graphic complaint filed in state Supreme Court in Manhattan, the woman alleged Adams sexually propositioned her 30 years ago while the two were sitting in his parked patrol car. Adams has denied the incident occurred.

In the wake of the allegations, Adams, via the Law Department, retained the services of Alex Spiro, a private attorney known for his celebrity client roster — a decision that sparked consternation at the agency, according to a report in the New York Post . Spiro is now serving as co-counsel on the case with municipal attorneys — an unusual arrangement for an agency whose expertise is defending city employees.

“That would be an uncomfortable situation,” a former government attorney, who was granted anonymity to discuss internal decisionmaking, said in an interview. “City Hall is saying: Even though this is what you do, we don’t trust you enough to handle it, and we want our own person. It’s kind of odd.”

Adams pushed back on that idea in an April press briefing, indicating Hinds-Radix made the call to hire Spiro.

“My confidence in the Corp Counsel is clear because they make any decisions on how to defend something,” Adams said.

Hinds-Radix often clashed with Brendan McGuire, the mayor’s former chief counsel, according to one of the people who spoke with POLITICO — a product of both differing styles and divergent job descriptions.

Friction between the corporation counsel and the mayor’s chief counsel is baked into the roles: The corporation counsel represents all of city government, which includes frequent mayoral adversaries like the city comptroller, the public advocate and the City Council. Whoever occupies the top slot must balance their decisions to account for those discrete constituencies, while the chief counsel is solely focused on City Hall.

And those jobs have become more distinct in recent years.

In 2019, a ballot referendum made the corporation counsel role subject to advice and consent from lawmakers in the Council, who have made sure to extract assurances that mayoral nominees will look beyond the needs of City Hall, putting more distance between the mayor’s office and the city’s chief lawyer compared with the years before the measure.

Garcia did not address Hinds-Radix's relationship with McGuire, who still represents Adams through his private white-shoe law firm.

When Hinds-Radix officially left at the end of May, the mayor commended her work.

“Sylvia Hinds-Radix played a critical role in furthering this administration’s vision to protect public safety, rebuild our economy, and make our city more livable,” he said in a statement at the time.

Hinds-Radix has said virtually nothing about her rocky departure from city government and her future plans, aside from a letter sent to colleagues in the Law Department.

In May, however, she did disclose some frank thoughts about how attorneys should comport themselves in contentious situations during a commencement speech at New York Law School.

“Be an advocate for your client, and in your advocacy always be honest, true and ethical,” Hinds-Radix said. “The ethical position that you take may not always please those around you or the ones you’re giving it to, but it will reward you in shaping who you are.”