On a recent afternoon in Harlem, Alvin Bragg, a former federal prosecutor who is now a visiting professor at New York Law School, was reminiscing about all the occasions — and there are many — in which he was wrongly held at gunpoint by the police. “Right here is the first time I was stopped,” Bragg, 47, told Jewish Insider as he stood at the corner of 139th Street and Adam Clayton Powell, Jr., Boulevard, just around the corner from his childhood home on Strivers’ Row. 

Bragg was 15 or 16 at the time, en route to buy bread and juice for his father, when an unmarked car suddenly began driving across traffic, heading in his direction. “They pulled up right around there,” he said, pointing to the curb, “and then they jumped out.” Bragg didn’t know what was happening until he glimpsed a badge dangling from an officer’s neck. “They had the gun to my head, and they were kind of stuffing their hands in my pockets,” he said, “accusing me of being a drug dealer.”

Eventually, the officers noticed Bragg’s letterman jacket, which indicated that he was a student at an elite private school on the Upper West Side. “They said, ‘Oh, you go to that school, that’s a good school. You can go now,’” Bragg said. “And I went back home.” Later, seeking legal recourse, Bragg filed a civilian complaint, talked to the local precinct and went downtown for an interview, an ordeal he remembers as demoralizing, particularly for a young Black kid. The police officers were never identified. “That was really my introduction to the criminal justice system,” Bragg said. “It’s why I went to law school.”

Now that he is running to be Manhattan’s next district attorney, Bragg believes that such intimate interactions with the legal system — coupled with years of government service — make him uniquely suited to revamp the office amid a national reckoning over public safety and racial inequality. “I’m drawing from a place of personal and professional experience,” he told JI on a 20-block stroll through Harlem in late January. “It all ties together.” 

“That informs who he is,” said Adam Szubin, a lawyer at Sullivan and Cromwell LLP who has known Bragg for decades. “But one of the things that you sometimes see is people who have been unfairly targeted by the criminal justice system channel that into a place of rage.” Bragg, Szubin added, has taken a more constructive route. “The fact that he has those experiences is important, but I think even more important is what he’s done with them.”

Bragg’s holistic approach to the law, he argues, leaves room for empathy but also affords him the freedom to be ruthless when it matters. “I’ve done the cases that work on safety and have not done the kind of cases that are really just debasing and clogging up our system,” he said of his time working in the criminal division of the U.S. attorney’s office for the Southern District of New York and then in various high-profile roles with the New York State attorney general’s office. 

Throughout his career, Bragg has taken on a wide array of significant cases. He has prosecuted a business owner who laundered millions of dollars for the Sinaloa Cartel, investigated police misconduct and overseen lawsuits against Harvey Weinstein as well as former President Donald Trump. “We sued the Trump administration over 100 times,” Bragg said. 

His boast, while noteworthy, functions as an implicit critique of Cyrus Vance, Jr., the Democratic incumbent who has been accused of shirking some of his responsibilities because of two decisions in which he chose not to prosecute Weinstein for sexual misconduct or the Trump family for fraud. The idea that Weinstein could avoid charges while a homeless person might be prosecuted, say, for buying food and toothpaste with a counterfeit bill, was deeply troubling to Bragg. “That juxtaposition really just bothered me,” he said. 

Bragg was the first to announce his candidacy in the race to succeed Vance, whose anemic campaign reserves suggest he is unlikely to seek reelection in the June primary. The field has since grown exponentially to include former prosecutors Tali Farhadian Weinstein and Lucy Lang along with public defender Eliza Orlins.

Bragg has raised more than $1.3 million dollars since he entered the race in June 2019, according to recent campaign finance disclosures. That puts him in second behind Farhadian Weinstein, who has raked in $2.3 million. 

Bragg has also earned a number of notable endorsements, most recently Eric Garner’s mother, Gwen Carr. Others who have backed the first-time candidate’s campaign include former Rep. Charles Rangel (D-NY), former New York Gov. David Paterson and Preet Bharara, who was the U.S. attorney for the Southern District of New York until Trump fired him in 2017. 

“I got to witness Alvin’s skill, smarts and effectiveness up close when he worked under me,” Bharara told JI in an email, adding that Bragg “took on some of the toughest cases,” such as convicting a corrupt FBI agent and prosecuting two men who were blocking women from going into a Planned Parenthood clinic. “Again and again, he’s shown a readiness to stand up to powerful people and interests in the fight for justice.”

Bragg has long been poised to seek public office, a path predicted for him in a glowing profile published in the school newspaper of his alma mater, Harvard University. Its title? “The Anointed One.” The piece, which focuses on Bragg’s term as president of the Black Students Association, characterized the young leader as a conciliatory presence on campus known for working with groups that might not be considered traditional allies, like Hillel. And with his cherubic face and placid demeanor, Bragg does carry himself in something of a beatific manner — qualities that may be attributed to his faith. 

Bragg spent his formative years at Abyssinian Baptist Church in Harlem, where his youth minister was a young clergyman named Raphael Warnock. The church, Bragg recalled, instilled in him a spirit of activism that persists to this day. “I remember being the youth leader here and going out and whitewashing billboards,” Bragg said. “Back then it was just one after another menthol cigarette ad or 40 ads targeting pretty negative images of Black people.” He is still deeply connected to the church. “I’ve moved around but this has been my spiritual home for my entire life.”

Alvin Bragg on a recent stroll on the streets of Harlem. (Matthew Kassel)

Hadassa Waxman, a litigator at Proskauer Rose LLP, said she bonded with Bragg over their religious affinities when they worked together in the Southern District office. “We are practicing Jews, my family and I,” Waxman said, noting that she was impressed with Bragg’s dedication to the church “in ways that I haven’t really seen before.”

“I used to call him ‘senator’ or ‘reverend’ in the office,” Waxman said, recalling that Bragg would often show up dressed in a suit and tie because he had just come from teaching Sunday school. “It kind of caught on.” In the Southern District, Bragg earned a reputation as a gifted trial lawyer whose eloquent opening statements were widely admired by his colleagues, according to Waxman. “I would go watch him on trial,” she said. “It was a thing in the office. When Alvin was delivering a jury address, people would go.”

Later, in the attorney general’s office, Bragg was an equally calming presence during a particularly intense period, according to Amy Spitalnick, a former communications director and senior advisor for the New York attorney general who is now the executive director of the nonprofit organization Integrity First for America. After the presidential election in 2016, Bragg led an effort to release a bulletin urging law enforcement officials to remain vigilant amid an uptick in hate crimes across the state — an advisory regarded as “enormously helpful,” Spitalnick said. “I still point to that as an example of what people can do at state and local government.”

The Manhattan district attorney will likely face similar challenges as hate crimes have remained a pressing issue, according to Spitalnick. “Having someone who gets it, who gets the importance of taking on antisemitism and racism and extremism in a variety of forms,” she said, “is just so crucial here.”

“I’ve been speaking out about it for years,” Bragg told JI. “We need leadership from the top.” Bragg argues that the current hate crimes unit in the Manhattan district attorney’s office is insufficiently staffed and inaccessible to regular New Yorkers. “We need to change that.”

But more broadly, Bragg insists that the office needs a full-scale renovation if it is going to help bring about a fairer system. He believes that many cases are a waste of resources, and wants to instill a culture that is proportionally less punitive when it comes to misdemeanors. “You’ll be evaluated not on how many convictions you get, because that’s not a measure of public safety and public health,” Bragg said of his expectations for staffers. “You’ve got to tell people what you want to do, and you’ve got to hold them accountable,” he said. “And when they do what you want them to do, you’ve got to have a system of promotion and rewarding around those principles.”

Bragg takes a measured approach to police funding — an issue he has studied in depth. “We need to focus on the substance,” he said, adding that he has called for cuts to the police budget in three areas: homeless sweeps, mental health responses and policing in schools. He thinks that rank-and-file officers in New York will agree with his evaluation. “I’ve worked with law enforcement officers,” he said. “The ones I’ve worked with will tell you they didn’t go to the academy to do homeless sweeps. They realize that that’s not public safety.”

Christina Greer, an associate professor of political science at Fordham University, said Bragg’s semi-moderate message has a strong chance of standing out in the packed race. “I would argue, of the candidates I’ve looked at, he has the most 360-degree view of what the borough needs,” she said. “By no means is he the most progressive candidate, but we’re also looking at an incredibly diverse borough of Democrats where, as we’ve seen in other races, I think voters want someone who has an understanding of the judicial system but in a pragmatic sense.”

“It seems as if Bragg’s resumé is speaking to that pragmatic progressivism,” Greer said. 

Ravi Gupta, the founder of Arena, a progressive political action group that supports fledgling candidates, said the decision to support Bragg was a no-brainer. “He started with this very organic case for why he should be the DA,” Gupta said. “The values that he talks about are not just on paper, but they’re deeply held and come from a very long history.”

“Having spent my whole life here, I love the island, and I want to see public safety and civil rights here for us first and foremost,” Bragg told JI during the recent walking tour of Harlem, where he lives with his wife and two children. “We set the pace in everything, as it should be, I think, as a Manhattanite, and so I’m excited not only about being able to do it here for us, but to set a national model.”

As he approached the intersection of 132nd Street and Frederick Douglass Boulevard, Bragg was reminded of another harrowing encounter with the police. “This one I’ll never forget because we were coming home from playing basketball with a bunch of friends,” he said. As they piled into a cab, he recalled, a veritable army of cops — police vans, a SWAT team — swooped in, guns drawn.

“They said someone had been stabbed in Central Park,” Bragg said incredulously. “I don’t think it’s a coincidence that the tallest and darkest of us was taken to the side and got a gun put to his temple.” The memory of the event still seemed raw as he thought back on what had transpired. “You want to talk about the absolute wrong way to try to elicit truthful information?” Bragg said. “Putting a gun to someone’s head for five minutes and telling them what to say?”

When it became clear that nobody had a knife, Bragg and his friends were free to go, in a manner of speaking. “They let us leave,” he told JI, “50 police officers later.” Now, as he makes his first bid for public office approximately 25 years later, Bragg wants to ensure that such experiences remain in the past.