Shortly before midnight on July 14, 2018, Tomas Medina was outside a car dealership in Washington Heights, in the northernmost part of Manhattan, hanging out with friends and listening to music coming from a speaker. Then came the police.

What followed became the subject of a civil lawsuit in federal court.

A police officer placed Medina in a chokehold, a banned move, for 23 seconds and later tased him 13 times from a close distance, according to documents filed in Manhattan federal court. Later on, Medina was handcuffed to a post, his pants pulled down to his ankles, while another officer slapped his back.

After a legal battle lasting more than a year, Ishita Kala of Covington & Burling LLP and her team, working with The Legal Aid Society of New York, secured a settlement on July 20 for the brutal treatment Medina received from the cops.

"It really is an absolutely egregious incident," Kala told Law360 Pulse. "It's dehumanizing and inhumane, and it's a brutal assault."

In the $567,500 settlement, the city paid $295,000 to Medina and $267,500 to his counsel. Fabio Nunez, the police detective that first confronted Medina, agreed to pay him $5,000 out of pocket.

"Being attacked by the NYPD was one of the scariest things to ever happen to me. I could have died," Medina said in a statement announcing the settlement. "What they did to me, and what they do to so many other people is not okay, but I take some comfort in knowing that Detective Nunez is no longer a police officer and that both he and the City have to pay for what they did to me."

Nicholas Paolucci, a spokesman for the New York City Law Department, which represented the police department, said the settlement "was in the best interest of the city."

James M. Moschella of Karasyk & Moschella LLP, who represented Nunez, said the officer agreed to settle the suit with Medina to avoid being left alone in defending it.

"It was purely a business decision," Moschella said. "Once the city decided to commit a substantial amount of money towards the settlement, it was really a no-brainer for Detective Nunez to contribute towards that settlement so that the claims could be dismissed against him."

Nunez never admitted to violating Medina's rights in agreeing to the deal. The cop continues to maintain that Medina caused their encounter to escalate, Moschella said.

"Nunez did the best he could to deal with a violent individual who was resisting arrest," Moschella said, whose firm regularly represents police unions such as the Detectives' Endowment Association and the Lieutenants Benevolent Association.

Medina, who at the time of the incident was 33, declined to be interviewed for this story. His lead counsel, Molly Griffard of The Legal Aid Society, pointed to a statement she made on the day of the settlement.

"While this settlement will never completely right the injustice that Tomás Medina suffered or dismantle the NYPD's culture of impunity for excessive force, it does provide some closure and sends a message to the NYPD that violence against civilians will be met with consequences. So long as the NYPD brutalizes our clients, we will continue to seek accountability and an end to NYPD violence," she said then.

That night, Nunez and another police officer, Shanee Hansler, approached the car dealership for a suspected noise violation and asked to whom the speakers belonged, demanding IDs. Medina walked away and went to help his friends who were packing up the sound equipment. As he turned his back on the cops, Nunez pushed him against a car and grabbed him by the neck.

Medina raised his hands in a pleading gesture, but Nunez escalated the situation, locking him into a chokehold as he attempted to put Medina under arrest. He then tased Medina repeatedly from a close distance, video recorded by a security camera, and later picked up by media outlets, shows.

Medina was charged with two counts of assault in the second degree and one count of resisting arrest in criminal court, but all the charges were later dismissed.

Court proceedings later revealed that Nunez told a fellow officer, "I would have choked him but I didn't want to do that because you would have get (sic) in trouble."

The 47-page civil complaint — filed in October 2019 against the eight officers involved in his arrest, department leaders and the city itself — went beyond just seeking individual justice for Medina, Kala said.

"What this matter and this incident comes down to is the NYPD's systemic failure to take affirmative steps to minimize the use of force against civilians and really is reticent to impose sufficient consequences for officers who utilize excessive force," Kala said.

Kala, a white-collar criminal defense attorney, said she got involved in the Medina case after seeing the video of his encounter with the cops.

"I was horrified at the behavior of the NYPD detective," she said. "I knew I had to work on this case to fight for Mr. Medina's rights and send a message that this is entirely unacceptable."

The Covington team she led included David Kornblau, Micha Nandaraj Gallo, Flannery Gallagher and Jessica Gerson.

The complaint filed by Covington and Legal Aid Society attorneys, said the officers who participated in Medina's arrest — about 20 cops arrived at the scene that night — violated his constitutional rights in various ways. They claimed false arrest and search under both federal and state law. They alleged the officers engaged in assault and battery. Medina sought compensation, punitive damages and asked a judge to compel the Police Department to address the misuse of chokeholds and tasers through training and by punishing bad actors.

But the heart of the suit was what is known as a Monell claim, from the 1978 case Monell v. Department of Social Services of the City of New York, with which a plaintiff can sue a municipality on allegations that a policy it knowingly adopted violates the rights of people who come in contact with municipal employees.

Medina's lawyers argued the Police Department failed to properly train officers to properly use tasers and to not use chokeholds, and that the police leadership failed to establish a real system of accountability for officers that deviated from the department standards. They also pointed to lobbying efforts by police leaders to criminalize the use of chokeholds and to allow the department to deal with violations of official chokehold policy internally, away from the eye of judges and local prosecutors.

The NYPD effectively banned chokeholds in 1993, citing a rising number of suspects dying in police custody involving the maneuver.

However, police officers have continued to use chokeholds. The death of Eric Garner in 2014 at the hands of a police officer who had placed him in a chokehold during an encounter caught on video by a bystander, triggered massive protests and ignited a national debate about police use of deadly force.

NYPD officers have been accused of using chokeholds in at least 40 federal civil rights lawsuits filed between January 2015 and June 2018. The city spent $1,236,502 to settle at least 30 lawsuits arising from police officers using chokeholds, the complaint says.

According to New York City Civilian Complaint Review Board data, the agency received 1,811 chokehold allegations from January 2009 to December 2018, the suit says.

There were nearly 1,400 suits filed over police misconduct in state and federal courts in 2019, according to Law Department data reviewed by Law360 Pulse. In 2020, there were just over 1,400. During the first six months of this year, about 700 suits have been filed.

"The NYPD is on notice of this custom — abusing chokeholds and tasers, and excessive force against civilians — and they are doing little to rectify it," Kala said.

Kala and her colleagues told the court the NYPD knew about officers using chokeholds and misusing tasers but did nothing to address the issue. Officers engaging in patterns of excessive force were not investigated, and when they were, they weren't fired, the complaint says.

Nunez has been the subject of 37 allegations of misconduct reported to the CCRB, arising out of 17 separate complaints, including some that involved the use of chokeholds. He has also been the subject of five separate settlement agreements involving alleged excessive force, which cost the city more than $220,000 in payouts, the Medina complaint says.

The NYPD shot back in court, saying Medina's lawyers didn't produce enough evidence to show that while officially banning chokeholds, the department tacitly allowed them in practice. It also argued that the officers had probable cause to arrest and search Medina.

Paolucci declined to comment on why Nunez was left looking for his own counsel.

"We don't discuss representation decisions," he said.

Under its policies, the Law Department may decide not to represent police officers in lawsuits if it believes they violated department rules or engaged in misconduct. Refusal to represent might also involve a conflict of interest: in a suit filed against both officers and the city over department practices, like in the Medina case, officers might shift blame by saying they were simply doing their job, while the city might claim the officers are liable for breaking the rules.

In the 15 months between Medina's arrest and the day the suit was filed, the Police Department defended Nunez's actions as justified. But on Feb. 25, 2019, the CCRB substantiated claims that the officer used excessive force in using the chokehold and misusing the taser. Nunez was hit with administrative excessive force charges and faced a departmental trial.

Moschella told Law360 those charges prompted the city to deny Nunez representation in the civil suit. The attorney filed cross claims against the city alleging a wrongful denial of representation under Section 50 K of New York General Municipal Law, which spells out the duty of the city to represent an employee in any civil action in federal or state court. Nunez agreed to drop those claims as part of the settlement, Moschella said.

Nunez also struck a deal with the department, agreeing to retire and forgo 30 vacation days.

A turning point came in November of 2020 when U.S. District Judge Alison J. Nathan allowed claims against Nunez, the Police Department's top brass, and the city to survive, while dismissing the ones against other officers, in an order that accelerated the parties toward a settlement.

Though Judge Nathan ruled Medina had no standing for injunctive relief, she said then-Commissioner James P. O'Neill and former Chief of Department Terence Monahan could potentially be held liable for knowing about some officers' use of excessive force including the banned chokehold, yet turned a blind eye.

"Medina has raised a plausible inference that the NYPD has maintained a custom of tacitly endorsing or tolerating the improper or unconstitutional use of chokeholds and Tasers. And Medina has also raised a plausible inference that O'Neill and Monahan were on notice as to the frequency of chokehold use," Nathan said in the order. "Plaintiff has sufficiently alleged a plausible claim that both O'Neill and Monahan were personally involved to the extent that they allowed a custom of improper chokehold use to continue."

Months later, the parties reached a deal.

--Editing by Alex Hubbard.

Update: This story has been updated with comment from Molly Griffard of The Legal Aid Society of New York.