Nearly two decades ago, the New York Police Department drew national headlines for its violent response to protests outside the 2004 Republican National Convention. Officers wrapped demonstrators in orange mesh netting and shipped them off to a dirty Manhattan pier, where they were fingerprinted and held, some for more than 24 hours.

The protesters sued, and after years of tense litigation, the city settled what the New York Civil Liberties Union then called the “largest protest settlement in history” — an $18 million payout to resolve claims that the police had violated the civil rights of about 1,800 people.

“While no amount of money can undo the damage inflicted by the NYPD’s actions during the Convention, we hope and expect that this enormous settlement will help assure that what happened in 2004 will not happen again,” Christopher Dunn, lead counsel in the NYCLU cases, said at the time.

But in June 2020, just six years after that settlement, history repeated. Facing mass demonstrations, this time in the wake of the Minneapolis police killing of George Floyd, the NYPD again became the focus of intense media scrutiny for its bellicose approach to protests, perhaps most notably for boxing in, or “kettling,” about 300 protesters in the Bronx before violently arresting them. Those protesters also sued, and earlier this month their lawyers announced yet another “historic” settlement, in which each protester would get $21,500. The total payout could cost taxpayers between $4 million and $6 million.

Now, the durability of that narrative is prompting some lawmakers to question not just the NYPD’s actions but whether the city effectively enables expensive payouts by aggressively defending against charges of police misconduct instead of leveraging its legal might to pressure the NYPD to change its behaviors and practices. Indeed, while the city charter requires the Law Department to represent “the city and every agency thereof,” it also says the department should “maintain, defend and establish” the interests of “the people.”

In the Floyd and RNC cases, city lawyers fought tooth and nail in court against misconduct charges, employing a litigation strategy that challenged disclosures and claims at every turn — an approach that critics say can prolong cases and actually drive up costs.

“It’s a bad practice,” said Councilmember Gale Brewer, a Manhattan Democrat, who plans on questioning Law Department officials when they appear before the City Council’s Committee on Governmental Operations for a budget hearing on March 22.

“The public may not care about the person getting arrested or the cops, but they do care about the money,” she said of settlements to civil rights lawsuits. “It’s millions and millions of dollars. And there’s always a push — ‘How can you push those settlements to be less?’ Well, that doesn’t answer the question: Why do they keep happening?”

It is a line of inquiry backed by the Council’s speaker, Adrienne Adams, whose spokesperson said in a statement that “city attorneys can play a constructive role in preventing future violations of constitutional rights, and they should.”

“It is a disservice to our city and its taxpayers when an agency tasked with protecting them not only violates their rights, but also passes on the cost back to them,” said Mandela Jones, the spokesperson for the Queens Democrat. “It’s equally bad when that agency is enabled to continue engaging in this problematic conduct that repeats this cycle.”

Spokespeople for the mayor’s office, the NYPD and the Law Department did not respond to requests for comment about the hearing. The NYPD said in a statement earlier this month that the department had “re-envisioned” much of its training and policies around “large-scale demonstrations” after the Floyd protests based on the recommendations of “three outside agencies who carefully investigated that period.” The Law Department has previously told ProPublica it takes its ethical responsibilities seriously and litigates each case with an open mind. “While we work to vigorously protect the interests of the city in every case, we are always mindful that opposing parties are also citizens who should be treated with respect and whose claims should be evaluated fairly,” a department spokesperson said last year.

The public scrutiny follows a December report from ProPublica and New York Magazine that examined the city’s Special Federal Litigation Division, the little-known unit within the Law Department that exclusively handles federal civil rights lawsuits alleging abuses by police officers, jail guards and prosecutors. Former attorneys described a culture within Special Fed that prizes winning, even if it means drawing out cases with merit and negotiating them down to the smallest possible payout. The hard-line approach has sometimes drawn rebukes from the bench. Last year, for example, in the Floyd protest case, a judge dressed down a senior Special Fed lawyer for failing to obey court orders. The city has also been sanctioned multiple times for not turning over records in a timely manner. (That lawyer has since been fired, though she denied any wrongdoing.)

Many within the Law Department see themselves as guardians of the city’s treasury, and argue that aggressively defending police cases weeds out frivolous claims, preventing undeserving plaintiffs from obtaining public monies that could otherwise fund city services. But plaintiffs’ attorneys and advocates for police reform counter that Special Fed actually wastes money and public trust by aggressively, and sometimes expensively, defending cases involving clear police misconduct. The NYPD has previously said that any allegation it has “undue influence” over Special Fed and its defense of officers is “outrageous and inaccurate.”

The purpose of damages in federal civil-rights litigation is “to incentivize the government to change policy so it doesn’t face the same exposure for similar kinds of violations in the future,” said Gideon Oliver, a civil rights attorney who represents protesters. “It doesn’t work if the city and the Law Department view cutting those checks as just the cost of doing business.”

Settlements and payouts for police misconduct cases totaled $121 million last year, up from about $85 million the year before, according to an analysis of city data by the Legal Aid Society, the city’s primary provider of indigent legal services. (The sharp increase was largely attributable to six payouts of $10 million or more stemming from decades-old wrongful conviction cases.) A Washington Post analysis of settlement data last year showed that, between 2010 and 2020, more than 5,000 NYPD officers were named in two or more claims, accounting for 45% of New York City taxpayer dollars spent on misconduct cases.

Meanwhile, the full price tag for lawsuits related to the Floyd protests will likely grow well beyond this month’s multimillion-dollar settlement. As of last July, 565 claims had been filed over the NYPD’s policing of the demonstrations, according to records maintained by the city’s chief financial officer, with 220 of them having cumulatively settled, many pre-litigation, for nearly $7 million. A consolidation of lawsuits that seeks widespread reform of how the police handle protests is also still active in Manhattan federal court.

An effort in the early years of then-Mayor Bill de Blasio’s first term sought to change the culture within the Law Department, pushing attorneys to think of their primary client as the broader public, not just the named officer in any given lawsuit. But that effort largely withered as the mayor’s relationship with the NYPD and its unions deteriorated. Brewer, citing the story by ProPublica and New York Magazine, said the role of the Law Department and how it represents the city should be subject to public debate. Lawyers for protesters agreed.

“The Council has an important opportunity when it’s approving its budget to demand that the city take a different approach to widespread NYPD legal violations,” said the NYCLU’s Dunn, who is also working on Floyd protest litigation. “When they’re there asking for large sums of public funds, the City Council should be demanding the Law Department be more responsible in the way it's addressing litigation like this.”