Damian Williams is taking on public corruption, pushing for federal oversight at Rikers and telling dad jokes

The 369th Regiment Armory, located on Fifth Avenue between 142nd and 143rd Streets, is named in honor of the U.S. Army’s 369th Infantry Regiment, an all-Black infantry unit better known as the “Harlem Hellfighters.” Formed in 1916 to fight in World War I, the regiment spent more time in combat than any other American infantry unit during the war. 

James Thomas Jr., a young Black attorney from Harlem, was one of the men who joined the regiment. While serving in France, he gained the respect of William Hayward, the white commander of the regiment and a fellow attorney. The two remained close after the war. In 1921, President Warren Harding named Hayward the U.S. Attorney for the Southern District of New York, and Hayward promptly hired Thomas – making him the first Black assistant U.S. attorney in the history of the southern district.

A century later, history was made again when Damian Williams was sworn in as the new U.S. attorney for the Southern District of New York, becoming the first Black man to ever lead the storied federal prosecutor’s office. Unlike many of his predecessors whose ceremonies were held within hallowed judicial halls, Williams chose to swear his oath at the Harlem Armory. Flanked by his wife Jennifer Wynn and his mentor, U.S. Attorney General Merrick Garland, Williams reflected on Thomas, Hayward, his immigrant parents who had come to America 50 years earlier and the generations of others who had made his appointment possible during his speech. 

“I wanted the focus to not be on me making history, but instead on the history that made me,” Williams told City & State, remembering the pivotal moment more than two years later. “As hard as I’ve worked, as lucky as I’ve been – I’m here because of folks you’ve never heard of, who made certain decisions, who did certain things that were much more courageous than anything I've ever done."

In the two years since he took the reins of SDNY, the office has taken on high-profile cases like crypto swindler Sam Bankman-Fried, Wall Street bullies, international terrorists, gun and fentanyl traffickers, and powerful politicians. Williams cemented himself as someone willing to speak with “moral clarity” last summer when he came out in favor of a federal receiver seizing control of New York City’s jails. In November, Williams again captivated the city’s political world when FBI agents seized New York City Mayor Eric Adams’ electronic devices, bringing what seems to be a sweeping federal probe into his 2021 mayoral campaign into the public eye. (Adams has not been accused of any wrongdoing.)

Interviews with over a dozen of Williams’ former teachers, colleagues, mentors and friends paint a portrait of an official driven by duty and bound to a moral code centered on fairness. Williams traces the driving force of his professional ascent to his parents’ decision to emigrate from Jamaica to the United States. 

Acutely aware of the distance they traveled and all that his family had gained as a result, Williams grew up wanting to give back and prove that his family and his country were right to welcome one another. As he got older and gained a better understanding of the flaws entrenched in American society, that desire steered him toward the law, blooming into a strong moral compulsion to try and better things with a nonpartisan hand.

Finding his path

On paper, Williams, 44, couldn’t be more exemplary. His glittering résumé paints a portrait of a brilliant, dedicated young man who soared seamlessly from Harvard to Cambridge to Yale Law School to two of the most prestigious clerkships in the country. But this list of accomplishments obscures the personal struggles and crippling self-doubt that Williams has had to overcome since he was a boy. 

“We cheer the mountaintops, but we get real quiet about the valleys in between as if the valleys aren’t part of the journey too,” he told students at Columbia Law School during a commencement address last year. “It doesn’t make any sense to me. It never has. Show me a mountaintop without a valley. I’ve never seen it and I bet you haven’t either.”

The son of two Jamaican immigrants, Williams was born in Brooklyn at Downstate Medical Center and raised in Atlanta, Georgia. Williams describes himself in his early formative years as “a little Black boy with a bad stutter growing up in the Deep South.” Nothing came easy for him. 

Hoping to get admitted to the same prestigious private school as his older sister, Williams took an admissions test that would hang over him for years to come. According to the school, his IQ was extremely low – or as people said back then, “borderline retarded,” he told the graduating Columbia students. “Even at 5 years old I knew that was not good,” he added. On his second attempt, Williams scored much better, leading the school to propose a compromise: He could enroll, but the first IQ score would remain on his record and he’d be placed in “the slow class.”

Within a few years, Williams moved to the fast class. He served as student graduate president in his senior year of high school and graduated at the top of his class. But the doubt stemming from the label he’d been slapped with as a young child never went away. With time, though, he has come to see it as a strength.

“I'm aware of my own blind spots,” Williams said. “I think the combination of self confidence and self doubt can operate together – to keep me honest, to keep me humble, and ultimately, to make me better.”

Williams’ path to the top of SDNY wasn’t linear. If someone had told his younger self that he would go on to become a U.S. attorney, he said, he’d probably have asked what that was. He didn’t know any lawyers, let alone prosecutors, growing up. The only thing he was sure about was his desire to find a way to give back to the country that had given his family so much. That was his compass as he wound his way through school.

His academic interests were wide-ranging. Williams said he viewed education as an intellectual exploration, not just a springboard to a good job. He studied economics as an undergraduate at Harvard University because he was curious about how markets worked. Hoping to understand why the U.S. was about to enter the war with Iraq in a post-9/11 world, he pursued a master’s degree in international relations at Cambridge. His initial decision to attend Yale Law School was fueled by a desire to understand how societies order themselves.

But a few weeks before he was set to begin law school, Williams’ carefully constructed academic world shattered when his 25-year-old sister Tiffani Simone Williams died unexpectedly from an infection after a root canal. “Anyone who has lived through not only grief but tragic grief – the kind that doesn’t make sense, where you’re going about your day and then suddenly it’s as if the world opens up and swallows you – that was what I was going through,” Williams said.

Harold Hongju Koh, the law school’s dean at the time, remembers Williams coming into his office one day and opening up about his loss and how he was struggling to focus. He’d assured him the best he could and the two continued meeting throughout the term. Koh recalls: “There was a real strength there. It was obviously the worst thing that had ever happened to him, but he was determined to help his family.” When Koh gave Williams the choice to not take his exams that term, Williams insisted on taking them.

“I didn’t really see him again until the spring of his first year. He came in and I was shocked. He was like a completely different person. Very sunny and cheerful,” Koh said. “He talked to me about how he’d spent a lot of time thinking about it and he’d dedicated himself to law school in memory of his sister. Then he really emerged as the leader of the class.”

“He wasn’t one of those students who talks every second and raises his hand in class, but he had this sort of quiet charisma and dignity and thoughtfulness that led everyone to sort of look at him as a leader,” recalled Heather Gerken, now the dean of Yale Law School. She remembers that Williams cared deeply about racial justice and was thoughtful in approaching difficult questions in an institutional setting. One particular paper that Williams turned in on the Voting Rights Act was powerful enough to change Gerken’s mind about how to approach the issue in class.

Having missed most of the summer internship application deadlines, Williams applied to SDNY unsure of what to expect. There he found an answer to what he’d always yearned for – a way to use his intellectual talents for the greater good and give back to the country.

“More than anyone I know, being in a position of public service and working for sort of the greater good has always been the thing that gets him out of bed,” said Ethan Fletcher, one of Williams’ longtime friends from law school.

After graduating from Yale in 2007, Williams clerked first for Garland – then a judge in the U.S. Court of Appeals for the D.C. Circuit – and then for Supreme Court Justice John Paul Stevens. 

Amid this blitz of early professional success, Williams’ personal life hit a new high. While on a routine bus ride from Washington, D.C., to New York, Williams – not normally one to talk with strangers on public transportation – and the woman sitting next to him struck up a conversation that has stretched on ever since. He and Jennifer Wynn, a clinical assistant professor at NYU Stern School of Business and founder of management consultancy Wynn Strategies, married in 2012 and are now the parents of two children.

The couple both describe their meeting as fate – one of those rare moments where the stars aligned. They later learned they had been born in the same hospital and that one of Wynn’s friends had even offered to give her Williams’ email address not long before they’d met. (She declined, not wanting to cold email a stranger.)

Wynn said Williams’ professional ascent has been a tremendous source of pride. But it’s also come with sacrifices at times, as they’ve poured themselves into one another’s dreams and the dreams they have for their children. Service, fairness and family have been defining themes, she said.

“Damian’s really loving and sweet and affectionate with the kids. It’s been really important to us and special to me to see that that hasn’t wavered despite a really big job,” she said. “He always has and still does sing Bob Marley songs to the kids at night when they go to bed. Lots of cuddles, and hugs, and kisses with the kids – dad jokes, of course, and playing sports with them.”

Following his clerkships, Williams spent a few years in the private sector working as an associate at the corporate law firm Paul, Weiss, Rifkind, Wharton & Garrison before landing back at SDNY in 2012 – this time as an assistant U.S. attorney. Focusing largely on white-collar crime, he came to lead the prestigious Securities and Commodities Fraud Task Force. In 2021, President Joe Biden appointed him the new head of the federal prosecutor’s office.

Reform and Rikers

The U.S. Attorney’s Office for the Southern District of New York is one of the most powerful and prestigious federal prosecutor’s offices in the county. It prosecutes everything from financial fraud on Wall Street and international organized crime to run-of-the-mill violations of federal drug laws. Williams is the first Black person to lead the office, and expectations were high when he got the job.  

“He gets the magnitude of the fact that he’s the first Black U.S. attorney for the biggest court. He also gets the magnitude of the fact that in the past some people who run that office have alienated other districts and other people,” said U.S. Attorney Trini Ross, the first Black woman to lead the Western District of New York, who was appointed within a week of Williams. “He doesn’t want to be that person. He really understands it from top to bottom and bottom to top.” 

For Williams, the heightened scrutiny was nothing new.

“Talk to anyone who was the first and I’m sure the answer would be the same. Yes, you feel an additional sense of obligation. The weight of the moment is kind of part and parcel of the job that comes with it,” Williams said. “But you know, one of the things about being a Black person in America is that you may often find yourself as the first in the space, the only in the space. So that kind of pressure isn’t necessarily a new thing. It’s just on a bigger stage.”

Williams has a strong sense of justice, shaped by his experiences growing up as the Black son of Jamaican immigrants. He believes strongly in the ideals of the country that welcomed his parents, though he is clear-eyed about the fact that the United States often fails to live up to those ideals – particularly when it comes to race and policing. 

“Damian was in some obvious ways a historic pick, (but) in many other ways he was essentially central casting for a U.S. attorney,” said Martin Bell, a Black former SDNY prosecutor. “He is whip smart, very principled, squeaky clean and somebody who buys into the office’s underlying ethos entirely. At the same time, he’s also somebody who recognizes the opportunity that he has enough that he’s willing to second guess a lot of things and be critical – even self critical – about a system that works.”

Central to Williams’ conception of justice is his belief that both white-collar and blue-collar crimes must be subject to the same standard of justice. As U.S. attorney, he has stressed “relentless enforcement” of corruption on Wall Street and in politics.

“I don’t think anyone is talking about there being a mass incarceration epidemic of powerful financiers on Wall Street and corrupt politicians,” Williams said. “If anything, people are worried about underenforcement of those laws, and I think it makes it even harder for the system to come across as legitimate if there is effectively a disparity.”

Under Williams, SDNY has been particularly aggressive toward financial fraud involving cryptocurrency. In December 2022, SDNY indicted cryptocurrency wunderkind Sam Bankman-Fried on numerous wire fraud and money laundering charges. After a high-profile trial, Bankman-Fried was found guilty on all counts and is due to be sentenced in March.

Jed Rakoff, a U.S. district judge for SDNY, said he has been impressed by Williams’ willingness to act decisively and tackle important cases in new areas like cryptocurrency. “That did not deter Damian at all,” Rakoff said of the Bankman-Fried case. “I also like that in that and in many other cases, he moved swiftly.”

Though hardly a radical criminal justice reformer, Williams has called for a reconsideration of how the federal justice system confronts race and discrimination. He has doubled down on anti-violence work and protecting communities that have historically borne a disproportionate amount of violence. 

“There's not this binary choice between public safety and good policing. People can have both,” he said. “We're not lawmakers. We don't promulgate policy … but it doesn't mean that we can't do things every single day to advance the cause of justice – to use our discretion fairly, to use our power wisely.”

Bell said Williams has shown creativity in tweaking “long-standing office machinery” with respect to some criminal justice questions and in reaching out to communities impacted by the criminal justice system. 

Others in the criminal justice space, particularly those who have appeared in court opposite SDNY, have questioned Williams’ commitment to reform. A defense lawyer familiar with federal practice in SDNY said that under Williams, the office has been just as aggressive, if not more so, when it comes to charging mandatory minimum sentences. 

“It’s been disappointing,” this attorney said. “There’s really no difference between him and any Republican or Trumpian U.S. attorney. They don’t actually seem interested in reform.”

“His talking points might make people think, ‘My God, this guy’s just a great progressive liberal reformer,’ but that’s not what they actually do,” the defense attorney added. “They’ll tout going after white-collar criminals, the rich and wealthy, that’ll be part of his talking points, but that’s a tiny fraction of their docket.”

Though the day-to-day practices of this office may not have changed much, there’s at least one high-profile case in which Williams’ focus on criminal justice reform has made a real difference.

Last year, SDNY joined a long-standing legal effort pushing for a neutral outside authority, known as a federal receiver, to take control of New York City’s jails system. 

The city’s jails have been besieged with violence for decades, and a class-action lawsuit originally filed by The Legal Aid Society led Rikers Island to be placed under the oversight of a federal court-appointed monitor in 2015. Reforms since then have been fleeting, and in 2022, at least 19 people died while in city custody. Reports released by federal monitor Steve Martin have documented numerous ongoing issues, and support for receivership has steadily increased, although the final decision will ultimately be up to federal Judge Laura Taylor Swain, who has presided over the long-running case.

Williams had followed the crisis at Rikers Island for some time; the issue was the first briefing that he asked for as U.S. attorney. He first raised the prospect of placing Rikers under a receiver in April 2022, writing in a letter to Swain that SDNY may have no choice but to pursue “aggressive relief.” He held off on taking any decisive action until July 2023, when he declared that SDNY would seek a court-appointed receiver. Looking back on the announcement, he said he felt it was important “to speak with moral clarity” on the issue. The office formally joined The Legal Aid Society’s long-running effort in November. 

“There's no magic wand,” Williams said. “If there were one, someone would have used it by now. But we do think that the receivership is the last best option to save Rikers Island,” he said.

Mayor Eric Adams’ administration has fiercely opposed receivership, insisting that the city is perfectly capable of reforming the jails complex on its own. But Williams remains hopeful that Adams will come around.

“This is an opportunity for this administration to join with all the litigants who are pushing for reform, and to use the receivership as a way to finally get some of the reforms that they say that they also want, but haven't been able to achieve,” he said.

Hernandez Stroud, senior counsel for the Brennan Center for Justice, said Williams’ recent actions have demonstrated a serious interest in realizing the constitutional rights of people incarcerated at Rikers Island. It’s noteworthy that SDNY joined the legal brief in the first place, he said, since with perhaps one exception, the Department of Justice has never been a party on a prison or jail case that went into receivership.

“Judges view the government favorably,” Stroud said. “When you have the federal government saying or urging a particular course it really does aid it … it gives greater credence to the argument that’s being advanced by The Legal Aid Society.”

Independent and incorruptible

More than two years after he stood at the Harlem Armory and was invested with the powers of U.S. attorney, Williams has gained confidence in the role and begun to take on even more high-profile, controversial issues.

Last month, he announced the creation of a new whistleblower pilot program and the addition of two new priorities for SDNY’s criminal enforcement: the fight against public corruption and the fight against the fentanyl epidemic.

SDNY is currently investigating Adams’ 2021 mayoral campaign fundraising. The full scope of the inquiry is not yet clear, but it appears that federal prosecutors and the FBI are examining possible criminal activity, including whether the campaign conspired with members of the Turkish government to receive illegal donations. 

The surprise seizure of Adams’ electronic devices in November – which Williams must have authorized – has led some legal experts to suggest that there is likely strong evidence that someone, be it the mayor or someone in his orbit, has broken the law. With SDNY’s long history of charging various lawmakers and NYPD officials for bribery and corruption, the city’s political realm has speculated about whether the investigation will yield Williams’ next big public corruption case. 

Unsurprisingly, Williams declined to comment on the ongoing investigation. He did, however, agree to speak broadly about the issue of public corruption. “Corruption is not costless,” he said, noting that the state has long had a public corruption problem.

“I don't know anyone out there who doesn't think that the state can do better, that our public institutions can do better,” Williams said. “I want to do my part, I want this office to do its part to send the message that compliance with the law is not optional. Breaching the public trust is not something that we will easily forgive.”

As U.S. attorney, Williams has already pursued a handful of high-profile public corruption cases involving influential people like New Jersey U.S. Sen. Bob Menendez and former Lt. Gov. Brian Benjamin. Earlier in his career as an assistant U.S. attorney, Williams helped convict Sheldon Silver, former Democratic speaker of the Assembly, on corruption charges. 

While assembling a new team of prosecutors for the Silver retrial,  Joon Kim, acting U.S. attorney for SDNY from spring 2017 to 2018, appointed Williams to the corruption unit, believing he had the trial skills and judgment to handle the case. The 2018 conviction was a significant victory for the office. As U.S. attorney, Williams has continued to build on the office’s history of taking on corrupt public officials.

“He leads an office from which a real positive impact can be made in areas important to our community, the city, and the country.  Damian appears to have used his position well, including with his focus on public corruption,” Kim said. 

Federal law experts have praised Williams’ new SDNY Whistleblower Program, which allows people to earn immunity from felony convictions in exchange for proactively alerting the office to wrongdoing and cooperating with the subsequent investigation.

Taking on allegedly corrupt public officials carries more political risks than taking on crypto fraudsters like Bankman-Fried, and already politicians have accused Williams and other federal prosecutors of politically motivated prosecutions. Former President Donald Trump has alleged as much on multiple occasions. So has Menendez. Even Adams has suggested as much, albeit in vague terms.

When asked how he balances the imperative to prosecute people who are breaking the law while also respecting the preferences of voters, Williams insisted that SDNY never does anything during investigations with the intention of influencing election results or helping or hampering a candidate. 

Still, he is cognizant of how some peoples’ reactions to the work of SDNY and other federal prosecutors has evolved. “An institution like this can no longer assume that everyone is going to conclude that everything that we do is rooted in good faith, even though it is. There was a time where I think we got the benefit of the doubt a lot more,” he said.

But while he feels he has an obligation to better explain SDNY’s work to the public, the shift hasn’t changed how the office does it work. 

“Our North Star remains that we do the right thing the right way for the right reasons,” Williams said. “That’s it. We are politically independent and incorruptible, full stop. That never changes, regardless of what people are saying about us.”

Besides public corruption, Williams’ other major priority for 2024 is combating the fentanyl epidemic, which he said has occupied an increasingly substantial portion of SDNY’s enforcement work. One big case led to the charging of a handful of individuals connected to the poisoning of four children, one of whom died of a suspected fentanyl overdose, at a day care in the Bronx.

There’s one solution to the overdose crisis that Williams is not so sure of – overdose prevention centers. Two of these supervised consumption sites, which provide a safer facility for people who are addicted to opiates, currently operate in Manhattan, and supporters have credited them with saving lives. But their current legal status remains ambiguous. Over the summer, Williams publicly warned that supervised consumption sites were illegal under federal law and said that his office was prepared to “exercise all options – including enforcement – if this situation does not change in short order.” 

Williams has not decided whether he is going to bring a civil enforcement action against the operators of the overdose prevention centers, but said that he feels he may have no choice if the city and state do not formally legalize them. He said that he made the statement to highlight how the sites are currently operating outside the bounds of the law. He added that there are ways to legalize them under state law – including legislation pending in Albany – that have not yet been taken.

The road ahead 

Williams may soon find himself out of a job. U.S. attorneys are nominated by presidents – and if Donald Trump defeats President Joe Biden in November, this could be the last year Williams leads the office. So what’s next for him?

There’s a long legacy of SDNY U.S. attorneys moving to other high-profile offices after their tenure ends. Throughout the office’s long, storied history, its leaders have gone on to serve on the Supreme Court, as judges and senators, U.S secretaries of war and homeland security, police commissioner, Manhattan district attorney, FBI director – even a New York City mayor. Thomas, the Black assistant U.S. attorney whose story has inspired Williams, went on to win election to the Assembly. 

Williams said he is not interested in running for elected office. The fact that his role is nonpartisan is one of the things he enjoys most about being a U.S. attorney. His brief stint in politics working on John Kerry’s presidential campaign was enough to convince him that elected office wasn’t for him.

Some of his friends think he’d make a good judge. A few think he should run for office after all. Many say that whatever he ends up doing, they are sure he’ll remain in public service one way or another.

“I can imagine him doing a lot of things. I genuinely think that despite the mountain of career potential energy that he’s sitting on top of right now, I don’t know or think that there is some sort of grand plan,” Bell said. “I think that he believes enough in the U.S. attorney’s office, and the job and the opportunity, that I suspect he is squarely focused on making sure that his legacy as a U.S. attorney is memorable and positive. I suspect he thinks that if that goes well, a lot of other things will take care of themselves.”

When asked what he wants to do after his time leading SDNY comes to a close, Williams balked. He said he’s not sure – it’s hard to think about. It’s a place where his two children often come to the office on weekends to watch cartoons and pretend to be U.S. attorneys – or “super chief,” as they call it. He loves what he does – his only job is to do the right thing. 

“This is my dream job,” Williams said, “and it's really hard to think about the day after you wake up from a dream.”