How Hakeem Jeffries Learned to Fight Dirty

The televised debate concluding the 2000 race for a Brooklyn seat in the New York State Assembly was just heating up when a 29-year-old lawyer with bright eyes, a carefully groomed mustache and a sharp tongue named Hakeem Jeffries went for the takedown.

“The issue in this race is not age,” he said. “Yes, my opponent is older; I’m younger. It’s not religion. Yes, the assemblyman is a practicing Muslim, and I grew up in the Cornerstone Baptist Church.”

His opponent, a 20-year Democratic veteran of the State Assembly named Roger Green, seethed.

“Practicing Muslim?” Green responded. “I’m absolutely offended. … Are you trying to polarize our community?”

Green had had enough. He stood up and walked off the NY1 set.

The incumbent had reason to be angry; few people in the district were aware that the long-serving Assembly member was Muslim: “It was an interesting piece of news that only a handful of people in Brooklyn probably knew,” recalls Errol Louis, the New York-based journalist and television host who was also a young political aspirant in central Brooklyn at the time.

Jeffries’ quip injected a new line of attack into an already bitter campaign. In the end, voters stuck with Green by a 59 percent to 41 percent margin. But Jeffries’ insurgent candidacy drew blood. The following term — during which discrimination against Muslims soared in the wake of the 9/11 attacks — the party establishment created a new legislative map that carved Jeffries’ home out of the district. Nonetheless, the two would spar again, and Green, fortified by the new boundaries of the district, would prevail once more.

Jeffries’ two losing campaigns against Green, a savvy veteran wielding the levers of incumbency, marked his first taste of political combat. For a politician who hasn’t had a difficult race in a decade, the two early races for the New York state Assembly stand out as moments that shaped his political identity. They provided enough strategic lessons for a dozen political science degrees, featuring everything from feuds over church-based organizing to fights over union support and a messaging battle pitting youth against experience and idealism against familiarity with power.

It would take Jeffries six more years to make it to Albany, and six more after that to earn a coveted seat representing Brooklyn in Congress, thus beginning his ascent to the top of the Democratic Caucus, where he stands just five seats short of becoming the nation’s first Black speaker of the House.

Now, the fact that his climb to power began with an attempt to draw attention to his opponent’s Muslim faith — an episode little remembered until now — sits uncomfortably with a man whose caucus includes three Muslim representatives, and whose political success relies on building multi-ethnic, multi-religious coalitions.

“As a first-time candidate, I spoke inartfully,” Jeffries says now. “It wasn’t an intentional line of attack.”

Jeffries regrets the incident, but maintains that the remark about Green’s religion was more youthful exuberance than purposeful dog whistle. After an oppressive summer of campaign events and candidate forums in which the two candidates remained largely civil but their supporters grew increasingly frustrated with one another, Jeffries didn’t believe he could let the opportunity to draw contrasts in a televised debate pass him by.

“[I] was directly challenging the Democratic machine and thought it was time to provide the community with an opportunity to go in a different direction,” Jeffries says.

But for Green, the attack was more than a simple drawing of contrasts — it got personal.

“I was a little hot-headed at the time,” Green says. “But I’ve been one who’s felt that there should not be any religious test for public office. As I served, I always tried to keep my personal beliefs as something that was not on my sleeve. … I always felt that was a private matter between me and my god.”

Jeffries believes Green’s dramatic show of protest — walking off the stage of a televised debate on New York’s most-watched news station — served to rally Green’s supporters, compounding the cost of his comment.

“It was an early lesson in communication. Anything you mistakenly say on the campaign trail can and will be used against you by your opponent in the court of public opinion,” Jeffries says. “Lesson learned.”

Green maintains that it’s a little more simple. He thought the attack line was premeditated, and he was so furious he couldn’t continue the debate.

“There had been a growing buzz in some constituencies about me being a Muslim,” Green recalls. “Probably a day or two days before that debate, I was in a coffee shop and I heard some folks saying, ‘Oh, well, he’s a Muslim, his wife must have to walk five steps behind him.’ Well, I’m not that type of Muslim. … I identify with a progressive mission of faith. I think I internalized all that … so then when religion was raised in the debate, I lost it.”

Jeffries’ opponent in a 2012 congressional race — the self-described Black liberation activist and City Council member Charles Barron, who notably refused to concede to Jeffries after losing, and whom Andre Richardson, senior adviser to Jeffries, recently called a “washed-up, irrelevant hater” — put the incident in harsher terms.

“Jeffries has no principles,” Barron says. “He’s a political animal opportunist. He will say and do anything to get where he’s going.”

Jeffries’ political career unofficially began in 1998, with a series of soundings that included a lunch at Tom’s Restaurant on Washington Street in Brooklyn, an old-school diner that still stands today.

At the time, Jeffries was 27 years old and a soon-to-be associate at the powerhouse law firm of Paul, Weiss, Rifkind, Wharton & Garrison. But he had stayed close to his Brooklyn roots, including his youth as an usher at the Cornerstone Baptist Church, which played a significant role in the civil rights protests of the mid-20th century.

Jeffries’ companion at the diner that day was Louis, the journalist and television host who had unsuccessfully run for local office himself in central Brooklyn. Jeffries wanted to ask Louis about the challenges of taking on an incumbent in New York. The incumbent he had in mind was none other than Green, whom Jeffries felt had gotten captured by the system after two decades in power.

Of course, the system has its rewards: Green had thrown his support behind Louis in his challenge to longtime incumbent City Council member Mary Pinkett a year prior, a fact that would prevent Louis from supporting Jeffries, he explained to the political neophyte.

It didn’t seem to faze Jeffries, Louis recalls. He described the challenges of taking on a well-ensconced Brooklyn politician. The young man still wanted in.

A year later, Jeffries put his political stake in the ground by volunteering for an effort to rectify Brooklyn’s persistent census undercount through raising awareness about its importance and persuading residents to turn in census forms. After distinguishing himself in that effort, a group of community leaders urged him to run for Green’s seat, according to Jeffries.

From his time at the high-powered New York law firm Paul, Weiss, he utilized fundraising connections across the plush precincts of the city; in the significant July periodic disclosure report in 2000, Jeffries reported raising $50,138 to Green’s $9,550, with many of Jeffries’ top contributions coming from well-heeled individuals living in ritzy areas of Manhattan, versus Green’s coming from local unions.

The numbers caught Green’s attention.

“I really was not one that was given to raising a whole lot of money into races,” Green says. “I usually relied on my social capital and the social capital of our organizations to get us our victories, but we had to raise money, that was new.”

Jeffries also leaned on the Cornerstone Baptist Church. An usher there when he was a child, Cornerstone Baptist remains a powerful pulpit; its longtime pastor, the Rev. Sandy Frederick Ray, who died in 1979, was a close friend of the Rev. Martin Luther King Sr. MLK Jr. called him “Uncle Sandy.”

Buoyed by the money and base of support from his church, Jeffries honed a message that attacked Green as an absentee Assembly member who wouldn’t pick up the phone when his constituents called and was letting unoccupied commercial spaces in the district fester.

It wasn’t so easy to tar Green, though. He was a well-respected member of the Assembly who was advancing his priorities in a difficult political environment; in 2000, New York state had a Republican governor (George Pataki), New York City had a Republican mayor (Rudy Giuliani) and the New York state Senate was controlled by Republicans.

Over the course of the summer of 2000 — which was “chilly enough to strain good humor” and included the coolest July in New York City since 1914 — Jeffries kept pushing, walking the district every day and accepting invitations at every community forum. He honed a clever two-step that would serve him well throughout his political career: Present yourself as an avatar of generational change without endorsing the more radical politics that often go hand in hand with youth.

Former New York Gov. David Paterson remembers noticing that Jeffries had an admirable sense of poise and equilibrium: He was a young man determined to succeed and mindful of not taking positions that would dog him in future races.

“He didn’t channel that kind of acrimony that many people do when they’re younger and they’re trying to be heard,” says Paterson, who was serving in the state Senate at the time.

According to Scott Levenson, a veteran Democratic consultant who worked with Jeffries through multiple runs for office, “What set Hakeem Jeffries apart from an early stage was his ability to raise money … and his ability to not alienate the establishment in the early years.”

Barron casts those early political instincts in a more negative light, calling Jeffries a “pseudo-progressive” and “corporate friendly.”

Jeffries’ carefully crafted image and army of young volunteers, though, ran right up against Green’s support from powerful unions like the 1199SEIU United Healthcare Workers and old friends in the district. He wouldn’t roll over and die, and with only around 10,000 likely voters, the fight for every vote grew increasingly heated.

Green won with a coalition of allies built over years of working and running for office in the district, but he notes that Jeffries tapped into a “younger typology of that same type of coalition” that was almost enough to topple him.

“This was no joke,” Green says. “When he came, he came with it real strong. … It really became kind of like athletes competing against each other.”

Jeffries’ strong challenge left the outcome in doubt, especially when he threw the wild card of Green’s faith into the ring. (Without public polling, experts from the time are split on which candidate the debate may have helped.) But the voters stuck with the veteran by a solid margin, 5,712 to 3,948.

Still, clearing the 40 percent threshold was a strong showing for a first-time candidate. The Brooklyn political machine — of which Green was a central cog — took the challenge personally. And after Jeffries’ sly reference to Green’s faith, it was happy to fight dirty right back; it went for a death blow.

New York State went through a redistricting process after the 2000 census. Jeffries, who was getting ready to come back at Green with a 2002 challenge, woke up one morning and found his home cut out of Green’s district.

While Green maintains that he didn’t even know where his young challenger lived, the new map looked like it took special care to target Jeffries, surgically removing his block from the district like a malignant tumor.

“I remember shaking my head in disbelief. … Brooklyn politics can be pretty rough, but that move was gangster,” Jeffries said with a wry smile in a 2010 documentary called Gerrymandering.

“That was pure Brooklyn,” Louis says of the redistricting process. “In the 1980s, it was absolutely typical in a campaign that a rock would be put through the window of a campaign [headquarters] or possibly the candidate’s house. It wouldn’t even merit a headline.

“The redistricting was a more genteel version of a rock through your window.”

New York law allowed Jeffries to run in the district for one more cycle, despite the fact that he no longer technically lived there. But with the new district lines also taking out some of the increasingly affluent neighborhoods where more of Jeffries’ voters lived, his support went backward; he secured only 38 percent of the vote.

Losing twice in a row almost drove Jeffries out of politics. He went back to practicing law. He had his second child in 2005; needing a bigger apartment, he moved just two blocks … and right back into Green’s district.

Whether Green heard Jeffries’ footsteps or simply had his sights set on higher office depends on whom you ask, but either way, Green took an unsuccessful shot in 2006 at running for Congress, challenging incumbent Rep. Ed Towns. In doing so, he vacated his Assembly seat. Jeffries was right there to pick up the pieces and apply the lessons he learned in his two races against Green to crush two challengers with 64 percent of the vote.

Indeed, Jeffries says he not only learned from his own mistakes, he emulated Green himself.

“Roger Green mastered the art of authentically putting together a coalition of organized labor, white progressives and traditional African American community support. That is a successful blueprint for winning races in central Brooklyn,” Jeffries says. “And I was able to follow that in a very competitive open-seat primary race in 2006.”

After at least eight years of plotting, Jeffries was finally an elected official.

His career since those early losses has been a fully vertical climb. In 2012, he challenged Towns in Congress and so thoroughly out-fundraised him that Towns dropped out before the primary; Jeffries defeated Barron with 72 percent of the vote after out-fundraising him by hundreds of thousands of dollars.

During the race, political luminaries in New York, including former Mayor Ed Koch and Rep. Jerry Nadler, also made a concerted effort to stop Barron, whom they described as antisemitic and a hate-monger. In a particularly colorful incident, former Grand Wizard of the Knights of the Ku Klux Klan David Duke endorsed Barron as an “anti-Zionist.” Barron tried to brush it off, but it dogged him in the campaign’s closing days. Barron lost every neighborhood in the district, including the predominantly Black neighborhoods that made up the base of his support. Today, there remains no love lost between the camps.

“It’s clear that Charles Barron has not gotten over the fact that Hakeem Jeffries destroyed him by 42 points, in one of the largest blowout elections in the history of supposedly competitive congressional races,” says Richardson, Jeffries’ senior adviser. “At some point, Charles Barron will be demanding that Hakeem Jeffries pay rent, because the House Democratic leader stays in his head.”

After only five years in Congress, Jeffries narrowly defeated Rep. Barbara Lee (D-Calif.) — an avowed progressive 24 years his senior — in 2018 to become Democratic Caucus chair after playing a familiar tune to fellow Dems: The importance of generational change. Ten years after he showed up as a freshman lawmaker, House Democrats by acclamation elected Jeffries to become their new leader. He brought Reps. Katherine Clark of Massachusetts and Pete Aguilar of California — both potential challengers — into a slate with him and helped all three of them get elected to leadership, with Clark as whip and Aguilar as chair of the party caucus. In doing so, he again used his well-honed political instincts to clear the field and get what he wanted.

“Losing twice at the start of my public service journey ultimately helped me to learn how to win and to deal with adversity,” Jeffries says. “That is a part of life’s journey.”

A lot has changed in New York City politics since 2000. But openly Muslim politicians remain rare. New York State Assembly member Zohran Mamdani, who found electoral success in 2020 as a Muslim candidate for office in Queens — running with the backing of the Democratic Socialists of America’s New York chapter — doesn’t think this is a coincidence.

“Since 9/11, but even before then, there has been a constant attempt at pushing Muslim New Yorkers to the margins and then over the edge,” Mamdani says. “If one of us were to be [politically] successful, it’s because we were incidentally Muslim. It was not something that was known to voters.”

So Jeffries’ comments in 2000 were not a particular surprise to him. “[Islamophobia] has become less explicit. … You might not hear the word ‘Muslim.’ You might not hear the word Islam. But you will hear about extremism or ties to specific groups or attempts at making associations that will block any consideration of a candidacy in a voter’s mind,” Mamdani says.

He cites a more recent example from Jeffries, when, he argues, the Democratic leader was ignoring the human rights of Palestinians, many of whom are part of the Muslim community in New York.

“One of the quotes that comes to mind clearly to me is when Hakeem Jeffries got onto a stage at a pro-Israel rally and paraphrased the words of George Wallace and said, ‘Israel today, Israel tomorrow, Israel forever,’” Mamdani says.

He’s referencing the late Alabama Gov. George Wallace’s quote: “Segregation now, segregation tomorrow, segregation forever.” Jeffries has used the Israel line at least twice, once in 2014 and once in late 2022.

For his part, Jeffries has made a living shrugging off the complaints of left-wing Democrats. The appellations bestowed unto Jeffries by media personalities of late — “bridge builder,” “reformer,” “measured,” an exhausting number of Obama comparisons — evince that he’s generally a moderate who believes mostly punching right but sometimes punching left will lead to better electoral success for the Democrats he now leads.

This can sometimes put him in a funny position. The hard-charging lawyer, who was happy to challenge a leader of the Brooklyn Democratic Party, can now operate the machine he was trying to break. Now, Hakeem Jeffries has to protect incumbents from people like a young Hakeem Jeffries.

Jeffries is quick to point out that he makes endorsements on a case-by-case basis. And he has, in recent years, endorsed challengers in New York State against some machine politicians. On a federal level, though, he has preferred to protect his caucus.

In 2022, Jeffries skirted questions on his endorsement of Rep. Henry Cuellar of Texas, the only anti-abortion Democrat left in the House, who has faced two intense primary challenges from a well-funded young attorney named Jessica Cisneros.

One of his first trips as House minority leader was to Laredo, Texas, a small town on the Mexican border represented by Cuellar, who showed him around. Some progressives saw the trip as a message that the new leader plans to back the incumbent to reassure the broader caucus and lock in someone who’s proved that he can win in November. If he does so, he’ll again be attempting to prevent the rise of a young, energetic lawyer who wants to take on an incumbent out of step with the modern Democratic Party.

The one major difference between the two young lawyers? Cisneros has embraced the progressive wing of the Democratic Party — getting endorsements from Bernie Sanders, Elizabeth Warren and Alexandria Ocasio-Cortez, among others — where Jeffries drew contrasts based more on his age than his ideological alignment, endearing himself to Nancy Pelosi.

Jeffries knows more than anyone that politics is a rough game. It’s not always fair. And maybe Cisneros, like Jeffries before her, has learned some important lessons from two straight losses. What’s important, he argues today, is to keep fighting. He’s learned, after early stumbles, to choose his words very carefully.

At an event at Cornerstone Baptist on Feb. 26, Pastor Lawrence E. Aker III asked Jeffries about his early electoral defeats. “After losing the first time and then the second time, it wasn’t easy, it was difficult. You get knocked down on the ground,” he said.

Then, he quoted Winston Churchill.

“Success is not final. Failure is not fatal. It is the courage to continue that counts.”

A few months later, I asked him what he learned from those early two defeats.

“Winston Churchill once said that, ‘Success is not final. Failure is not fatal. And at the end of the day, all that matters is the courage to continue,’” he told me.

More than 20 years since his fateful debate with Green, Jeffries has certainly improved his message discipline.