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On his road to becoming House Democratic leader, Rep. Hakeem Jeffries (D-NY) has had a complicated—and sometimes tortured—relationship with the left.

In recent years, the Democrat has spearheaded efforts to protect his party’s incumbents from liberal primary challenges, clashed with progressives on issues like Israel-Palestine, and decried the “extreme left” for being “obsessed with talking trash about mainstream Democrats on Twitter.”

Progressives have long criticized Jeffries—with a Brooklyn district that is, in one place, about a mile as the crow flies from Wall Street—for his coziness with the financial industry.

When he was just a New York state assemblyman in 2011, Jeffries cosponsored a “payday loan” bill that consumer advocates said was “predatory.” When he got to Congress in 2013, he split with the majority of Democrats to vote to kill a Dodd-Frank rule against risky trades. And according to OpenSecrets, in 2022, only two House Democrats running for re-election received more contributions from the finance and real estate industry than Jeffries.

On several high-profile occasions, Jeffries and his team feuded with the House’s most visible progressive, Rep. Alexandria Ocasio-Cortez (D-NY), who is one of the few members yet to tweet or issue a statement praising Jeffries’ election to the leadership post.And yet, as Jeffries prepares to step into the top job for Democrats in January, the party’s most progressive lawmakers aren’t preparing for war. Instead, most are welcoming his ascent—and even holding out hope that they could work more harmoniously with him than with his predecessor, Speaker Nancy Pelosi (D-CA).

“I do anticipate a good working relationship with the [Progressive] Caucus, and even those in the Caucus who are further to the left. I think he’s gonna work well with all of us,” said Rep. Jamaal Bowman (D-NY), who won a seat in the House in 2020 after defeating a Democratic incumbent endorsed by Jeffries. “It’s going to be a lot of disagreement and dialogue and debate, but I think, yes, I think he’s ready, willing and able to do that work.”

“Obviously, there are a few detractors,” Rep. Jared Huffman (D-CA), a newly elected member of Progressive Caucus leadership, told The Daily Beast. “But overwhelmingly, people feel good about who he is and what he stands for.”

The fact that progressives are welcoming Jeffries’ rise—and that he faced not even a perfunctory challenge from the left for the leadership gig—speaks to what is considered Jeffries’ greatest skill: relationship building.

According to several progressive lawmakers and aides, the question of whether Jeffries is actually a progressive himself is somewhat beside the point. However, he is a member of the Progressive Caucus in good standing, which requires backing most progressive policies, including items like Medicare For All, which Jeffries consistently has through his tenure.

Jeffries’ spokeswoman, Christie Stephenson, told The Daily Beast that, as chair of the House Democratic Caucus, “Rep. Jeffries prioritized and valued input from all parts of the family, including Progressives, New Dems and Blue Dogs. In his new leadership position, he will do the same.”

“Leader-elect Jeffries also plans to build upon a successful track record of defending House Democrats he serves with who have a proven track record of legislative success,” Stephenson continued. “In this most recent election cycle, he raised more than $17 million for his colleagues, battleground candidates and the Democratic Congressional Campaign Committee. His work is just beginning.”What makes progressives more optimistic is that his long-running engagement with them means he will be attentive to their concerns. One progressive aide said that Jeffries “comes to all the Progressive Caucus meetings, he’s vocal, he’s smart, he responds quickly to all the whips.”

“Just all of the little things,” this aide said, “that add up.”

For many on the left, there’s real value in having Jeffries—comparatively young at 52 years old and the first Black person to lead a party in Congress—at the helm.

“I don’t think it’s a foregone conclusion that Jeffries will be some major change agent,” the aide said, “but I think he’ll be a degree more sensitive to the need to lift up the new generation of progressives, and especially issues that affect people of color and minorities.”

There’s a paradox, however, behind Jeffries’ strength with progressives in the Capitol building: outside it, many of his relationships in the broader progressive movement are frayed at best.

Among the activists who elevated members like Bowman, Jeffries is seen as the champion of a Democratic establishment that has worked arduously to stop the progressive movement from gaining a foothold in Congress.

Ironically, that perception may run deepest in Jeffries’ hometown of New York City—and his home turf of Brooklyn, home to perhaps the nation’s most concentrated membership of the Democratic Socialists of America.

In that deep blue district, Jeffries is reliably re-elected by 50-point margins, and has plenty of progressive allies. But Rachel Himes, a DSA leader for the chapter that covers much of Jeffries’ district, described long-running exasperation with the congressman in their camp. They see him as a powerful figure who has needlessly antagonized progressive activists and candidates both at home and nationally. Not just that, Himes said he has been “hard to pin down” on—or outright opposed to—key agenda items like the Green New Deal.

Himes said she was “maybe disappointed, but not surprised” that Jeffries faced no internal opposition for the leadership post. “We want to see some of those lawmakers who are more outspoken on progressive issues holding him accountable, to the extent that is possible now,” she said. “Maybe there are lawmakers who, in good faith, see his new role as an actual opportunity for a new start in moving progressive legislation.”

The tension at the heart of Jeffries’ relationship with a key bloc of his party could shape how the newly minted leader approaches his task as the first new House Democratic leader in two decades.

“It is a very important relationship,” said Michael Hardaway, a former longtime aide to Jeffries.

As Pelosi was before him, Jeffries will be a top focus of attention and scrutiny for progressives both inside the Capitol and beyond it. When it comes to legislative action on issues like climate change and health care, progressive members themselves have often echoed activists’ demands and pushed for them at the negotiating table—one at which Jeffries will be leader.But for the next two years, Jeffries’ central charge will be returning Democrats to the majority. As he quarterbacks that effort, the way he approaches candidate recruitment, fundraising, and resource allocation could reintroduce past sore spots in his relationships with progressives.

“He'll get shit from the far left, you know, quite often, and sometimes justifiably,” predicted Bowman.

That is because, off Capitol Hill, Jeffries boasts far fewer fans in the progressive sphere.

Even before assuming the caucus’ top job, Jeffries built a reputation as an ardent defender of incumbent Democratic members—particularly those facing progressive challengers. He propped up the Team Blue PAC, which works to defend incumbents facing insurgent bids. Jeffries himself has hit the campaign trail in past primary cycles to go to bat for his colleagues.

That loyalty won him points throughout the Democratic caucus. Members saw that if they’re in a pinch or facing a rising progressive star, Jeffries would have their back. And he’s promised that won’t change while he serves in the caucus’ top spot.

But his work also left behind a trail of progressive hopefuls, organizers and activists who question his tactics.

Some wonder why he opted to spend time and resources during this past campaign cycle in overwhelmingly blue districts—meaning a Democrat was almost guaranteed to win the seat, regardless of who the nominee was.

In Illinois’ 7th Congressional District, for instance, there was no Republican running this year. So when progressive Kina Collins challenged longtime Rep. Danny Davis (D-IL), the seat was safe regardless of whether she or Davis won.

That didn’t stop Jeffries from jumping in. He went to the district to campaign for Davis in May. Collins questioned whether Jeffries and his PAC’s resources could have been used on competitive races instead, especially in a cycle where Democrats were overwhelmingly forecasted to, and ultimately did, lose control of the House.

“I want to see Rep. Jeffries build a coalition between progressives, moderates, independents even, across the country, and make sure that the resources that we’re using in these races are going toward the right things, like fighting Republicans, and allow the Democratic primaries to let the chips fall where they may.” Collins ultimately lost the primary by 6.6 points.

Team Blue endorsed this cycle against progressive Imani Oakley, who unsuccessfully challenged Rep. Donald Payne (D-NJ), a moderate member of the caucus whose father held the seat before him. While there was at least a Republican running in New Jersey’s 10th District, it was an overwhelmingly safe seat. Payne ultimately won re-election by more than 57 points.

Oakley said she doesn’t expect progressives on the Hill could have mounted a successful challenge to Jeffries for the job. But she was disappointed members didn’t at least call out his past work against progressive hopefuls before nominating him to the role, if only in an attempt to raise awareness about his complicated relationship with the left.

“I would have liked to see progressives be a lot more vocal on his shortcomings. Even if they did end up voting for him,” she said. “They could say something along the lines of, ‘Well, I voted for him, but you know, purely because I actually don’t like him. I just simply do not have the numbers to get somebody else in there.’”

But there’s, of course, a method to Jeffries’ work on the campaign trail, even if it was bound to rub some progressives the wrong way. One former Jeffries staffer told The Daily Beast that Team Blue has served in particular as a mechanism for protecting sitting Congressional Black Caucus members, who’ve now been a driving force behind his climb to leadership.

The staffer also noted Jeffries’ work protecting incumbents provided a currency of trust. Members knew he’d have their back—and in a world where redistricting can change the political makeup of a seat every few years, a leader who can play defense is valuable to even the safest House Democrats.

Even as Jeffries stares down the barrel of leading a caucus with over 100 card-carrying progressive members—the most in its history—he doesn’t seem daunted. “I have no issues with any member of the House Democratic Caucus,” Jeffries told reporters after his election to the post. He has also reportedly been courting members like Ocasio-Cortez, who told Axios in November that she had sat down with the new leader—for the first time ever.

A complicated relationship with the left is one thing that Jeffries will share with his historic predecessor. Pelosi often embraced the “San Francisco liberal” label that was part of her Republican caricature. That legacy helped her keep a measure of progressive credibility as speaker—though it may have diminished after years of pitched battles with progressives on key issues.

Jeffries, meanwhile, came up through hard-nosed, Democrat-dominated New York City politics, where ideology often matters less than coalition politics and personal relationships. But his allies argue his experience—and his upbringing as a Black man in working and middle-class Brooklyn—forged him into a staunch progressive.

“Hakeem has been a progressive his entire life,” argued his former aide Hardaway, who expressed befuddlement that there are people who believe otherwise. “Progressives will have more power this term than they ever had, because their leader is a dyed-in-the-wool progressive.”

The reason Jeffries has strong relationships with progressives, Hardaway said, is because they understand he is one of them. “Ninety-nine percent of what’s important to them is important to Hakeem,” he said.

Obviously, many progressives do not share that view. To Jeffries’ critics, Huffman, the California Democrat, had a simple message.

“They’re going to see some great leadership from this man,” Huffman said. “I wouldn’t ask any activist to stand down and stop fighting for more, but the smart activists understand that no leader is going to please them every single time. Let’s cut the guy a little slack and give him a chance to lead.”

Ursula Perano is a politics reporter at The Daily Beast, with a focus on progressives. She is a graduate of Florida State University and previously worked at Axios and Politico Pro. Send her tips: ursula.perano@thedailybeast.com or tips@thedailybeast.com. You can also use our anonymous document submission system, SecureDrop. Click here to find out how.

Sam Brodey is the congressional reporter for The Daily Beast. He previously was the Washington correspondent for MinnPost and a fellow at Mother Jones. Send him tips: sam.brodey@thedailybeast.com, or tips@thedailybeast.com. You can also use our anonymous document submission system, SecureDrop. Click here to find out how.

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