Christopher Aluka Berry / Reuters

Ben Jealous, a tall, gregarious man wearing a suit, stepped to the center of the room at Morgan State University. The comedian Dave Chappelle, wearing stylishly torn clothes and clutching a cup of coffee, took a seat on a table to the left. Jealous launched into one of his favorite stories, punctuated by Chappelle’s occasional interjections—the time Chappelle saved his life.

It was the early ‘90s, and the former NAACP chief was then a young activist organizing protests against Mississippi Governor Kirk Fordice, who had threatened to call out the National Guard rather than comply with a court ruling to fund his state’s historically black colleges. Fordice had suggested closing one of them and turning it into a prison. Jealous had just picked up Chappelle, his godbrother, from the airport in Mississippi. Shortly after Chappelle told Jealous that he had a dime bag of marijuana in his luggage, they were pulled over by a pair of police officers in an unmarked Ford Crown Victoria.

A white officer emerged with a nickel-plated .45 in his hand—“That’s not standard issue!” Chappelle observed—and told them to get out of the car.

“They give us very complex orders for getting out of the vehicle without getting shot, we do all that because we don’t want to get shot,” Jealous said. Then the white officer asked him, “Boy, where have I seen you before?”

“I’m trying not to say, ‘Yeah, I’m the high-yellow guy with wavy hair on the news each night leading protests,’” Jealous recounted. Just before he could answer, the other officer, who was black, asked Chappelle, “Boy, didn’t I see you on Def Comedy Jam last night?”

The audience roared with laughter, but Jealous wasn’t done.  

“I was terrified at that moment because we were two black men in America with a dime bag,” Jealous said. “We could have been in jail, and if something went wrong in that jail we could have still been in prison and you wouldn’t know who he was or me, we would have just been inmate XXXX.”

Jealous paused, squeezing his eyes shut, as he does whenever he’s about to make an important point.

“That’s why when I am governor, we will build a movement in this state and finally legalize cannabis for adult use.”

The audience laughed and cheered. But the appearance was a short one. Afterwards, I asked Gillian Spencer, a daycare worker, how she felt about Jealous as a candidate.

“He’s very effective in person, I gotta tell ya,” she told me. “I want to believe him.”

If he wins, Jealous would be only the fifth black governor in United States history, the first black governor of Maryland, and the first veteran of Vermont Senator Bernie Sanders’s presidential campaign to win statewide office. His candidacy poses a series of questions about bridging deep divides. Can a Democrat from Baltimore appeal to enough suburban and rural voters to put together a winning coalition? Can Jealous, a prominent Sanders supporter, and his running mate Susie Turnbull, a staunch Clinton backer, succeed in healing their party’s lingering fissures? And—the biggest question of all—has Jealous hit upon the formula that can pull minority voters to the polls while bringing the white working class back into the Democratic Party?

Donald Trump won the presidency by combining a superficial economic populism with appeals to resentment against religious and ethnic minorities. Jealous’s candidacy is a photo-negative of Trump’s: Economic populism fused with appeals to racial justice and equality. “We’re the only ones who can really unify the entire base of the party,” Jealous told a group of voters in the basement of Emmanuel Lutheran Church in Catonsville. “It matters that we can pull the whole party together, with the enthusiasm of everybody.”

But it’s not clear he’s right. Polls show him neck-and-neck in the Democratic primary with Rushern Baker III, an earnest and experienced technocrat who presided over an economic revival as county executive in the vote-rich Washington, D.C., suburbs of southern Maryland. Jealous is promising to unify his party, but it’s hard not to hear the echoes of the 2016 presidential race—this primary again pits a progressive outsider with ambitious goals against an experienced politician with a proven record of accomplishments.

“I think the difference between me and the other individuals running is really a record versus people’s rhetoric,” Baker told me. “That’s really what it boils down to, not about the policy.”

Baker’s predecessor as county executive in Prince George’s County was arrested for corruption, and Baker has been widely applauded for cleaning up the county and bringing businesses back to the area. Where Jealous is proposing sweeping policy changes like free state college tuition, single-payer health insurance and the legalization of marijuana, Baker’s plans are more modest—he wants to expand Maryland’s medical-marijuana system, and talks about reviving Baltimore’s Red Line transportation project, which was scrapped by Larry Hogan early in his term. Jealous tells the story of his family emerging from slavery to become activists, social workers, and educators, while Baker’s origin story is less sweeping—he was a military kid whose political awakening began with Richard Wright’s Black Boy, and who became a politician because he thought it was the best way to help people.

“When I read that novel, it let me know how blessed I was to have the type of parents that I did. And that made me feel guilty—that is what made me feel guilty about not doing anything at all with the blessings I had,” Baker said. “That’s what led me to the interest in public service.”

Baker subtly contrasts his approach to politics with a story about Howard “Pete” Rawlings, an influential state legislator who was Baker’s mentor. Early in his time in the Maryland House of Delegates, Baker gave a stem-winding speech about the budget. Rawlings came up to Baker afterwards and said, “That was a good speech. How many votes did you change?”

“I looked on the board. We had 141 members of the house, and I think two people voted with me,” Baker said. Rawlings told him, “If you really want to learn how to get things done for the people you care about, come see me. If you simply want to make speeches, then continue to do that, but you’ll never impact the people you care about.”

Baker says he learned a valuable lesson about politics, and the importance of results over rhetoric. “That was the beginning of a relationship where I went to see him, and he taught me how to actually get legislation through that can help the people that I wanted to affect most,” Baker said. “He taught me how to get legislation through the general assembly. Because if you can’t do that, you can’t get a single-payer health-care system, because you don’t know how the system works and you don’t know how to get it through.” Baker told me that lesson “is the difference between myself and the six individuals that are running for governor.”

Baker has compiled an impressive list of high-profile local endorsements: The Washington Post’s editorial board, Steny Hoyer, the number-two Democrat in the U.S. House, Maryland Senator Chris Van Hollen, and former Maryland Governor Martin O’Malley among them. Jealous, by contrast, has racked up a number of endorsements from national figures with their eyes on the 2020 presidential race, including Senators Sanders, Kamala Harris, and Cory Booker. He also managed to snatch the endorsement of the Maryland teachers’ union out from under Baker, whose record on education is seen as a potential weakness, as well as winning the Baltimore Sun editorial board’s endorsement.

Jealous also appears to have an edge over Baker on enthusiasm—as of May, he had received contributions from hundreds more donors, raising more than $605,000 to Baker’s $355,000, according to campaign-finance records. Political action committees backing Jealous have also raised large sums of money from wealthy out-of-state donors.

On the other hand, Maryland’s Democratic electorate has shown a soft spot for establishment figures. According to former Maryland Secretary of State John T. Willis, Maryland Democrats have chosen a candidate with prior elective-office experience every gubernatorial primary in the last hundred years but twice. Both of those candidacies ended in general-election losses: In 1954, Harry “Curley” Byrd lost after vowing that the University of Maryland would never be desegregated, and in 1966 George P. Mahoney lost after running against federal civil-rights laws with the slogan “Your home is your castle—protect it.” His victorious opponent was Spiro T. Agnew, who ran on a pro-civil-rights platform but turned against the movement after joining Richard Nixon’s presidential ticket.

Jealous, as a former NAACP chief, is obviously an insurgent candidate cut from a different cloth.

“We’re not going to win by tacking towards the middle. Hogan’s already staked out that zone,” Jealous told the voters in Catonsville. “We’re going to run by tacking towards the people of the state.”

A Bernie-style Democrat winning a state that went for Hillary Clinton over Donald Trump by more than 26 points doesn’t sound like a tough sell until you get to the details. Jealous is running to unseat Larry Hogan, a well-liked Republican governor who has carefully avoided Trump-style outbursts and has spent his term conceding key Democratic priorities—his approval rating is 70 percent. Fully a quarter of Democratic voters in the state plan to vote for Hogan in November, according to a June poll in The Washington Post. Hogan knows he’s in a state where President Trump’s name is mud—in June, after the outrage over the Trump administration’s family-separation policy, Hogan withdrew a Maryland National Guard unit helping patrol the border.

“There are progressive pockets in Maryland, but there are more moderates in the state,” said Mileah Kromer, the director of the Sarah T. Hughes Field Politics Center at Goucher College. “When you look statewide, progressives are a minority.” Conservatives in and outside of the state love Hogan—despite his moderation, he is seen as a necessary check on a deep blue state where a more conservative candidate couldn’t get elected. National Review’s Jim Geraghty compared Hogan to a goalie, “deflecting bad ideas and keeping the opposition from scoring.”

In other words, Hogan is in the strongest position a Republican could be to get reelected in Maryland. “I think the governor’s done a phenomenal job of going beyond the politics, not falling into the typical traps the Democrats try to set, in the state legislature and rhetorically,” said Michael Steele, a former chairman of the Republican National Committee and lieutenant governor of Maryland under Republican Bob Ehrlich. “By every measure, not just polls, the governor has the support of the people.”

Jealous’s bet is that by running as an unabashed progressive, he can generate enough enthusiasm from the Democratic base to overcome first his Democratic opponents and then the Republican incumbent.

“We turn out the unlikely voters, we will wallop Hogan,” Jealous told me in an interview. “I’m in this to wallop Hogan.”

Jealous likes to tell stories. He’s good at it.

To an enthusiastic crowd of teachers’ union members organizing to canvass for Jealous early one Saturday morning in June, he told the one about how his family members “have been educators since they walked out of slavery.” To the group of anxious, mostly white voters in the basement of Emmanuel Lutheran Church who wanted to know how he can beat Hogan, he talked about a Maya Angelou-quoting Trump voter who wants single-payer health insurance. When a woman asked him what he plans to do about school shootings, he spoke of two relatives who were victims of gun violence. Explaining his advocacy for undocumented immigrants, he said the first member of his father’s family to come to the United States “didn’t have papers.” He said that as a small-business owner, he’s “never seen a budget that couldn’t be optimized by 5 percent.”

And of course, he tells the story of his parents, the white man from Maine and the black woman from Maryland who met as school teachers in Baltimore, then fled the state for California once they realized their marriage would be illegal.

“We already have Loving v. Virginia, we don’t need Jealous v. Maryland,” Jealous says, explaining their thinking.

If Jealous’s biographical candidacy—telling the story of his family’s rise from humble beginnings under uniquely American circumstances—echoes runs by other black candidates, it also differs from them in important ways. Successful black candidates for statewide office typically emphasize the inspirational elements of their family history, the better to reassure white audiences that they hold the same unconditional reverence for flag and country. The ugly parts of American history are only mentioned to affirm that they were indeed overcome.

Jealous doesn’t tell his story that way. The story of Jealous’s family sounds a bit like a Barack Obama biography written by the historian Eric Foner. Sure, there are hope and change, and the allusions to how his mixed-race background can help him bridge any divide, no matter how stark. But the history of American racism—from slavery to Jim Crow to mass incarceration—frames every tale. The story he tells doesn’t end happily ever after. It only continues with the obligation that Jealous inherited from his ancestors, to fight the same system they fought, in whatever modern manifestation it takes.

The most important story though, is the one Jealous tells about Maryland, “the richest state in the richest country,” and his desire to do “big things” as governor. Jealous says he wants to “fully fund education” in the state—this winter, broken-down furnaces and burst pipes forced Baltimore schools to close. There’s the full legalization of marijuana, which Jealous believes will reduce crime in the state and lower its prison population. He expresses frustration that Maryland granted none of its medical marijuana licenses to black entrepreneurs, saying, “My dad’s a white guy, I want white men to do well, but that’s a pretty 19th century approach.” Jealous wants to make public colleges free for Maryland residents, which he says would be paid for through higher taxes on the wealthy. Most ambitiously of all, he wants to implement single-payer health insurance for the state, a plan even Vermont had to abandon over concerns that tax raises would cause an economic catastrophe in the state.

“Economies of scale matter. Vermont’s simply too small,” Jealous says when I ask him how his single-payer plan will work. “Vermont’s the size of Baltimore. Maryland’s 10 times larger.” Asked what form that state-level plan will take, Jealous demurs. “It’s going to work the way it does in Canada and France and England and every other Western nation,” he said, lumping together a widely varied set of systems.

Jealous lacks for experience in elected office, but he has drawn praise for his leadership of the NAACP, where he organized around rights for undocumented immigrants, abolishing the death penalty, and voting rights, and persuaded the organization’s board to fully endorse marriage rights for same-sex couples.

“He was regarded as an effective leader at the NAACP,” said Cornel William Brooks, Jealous’s successor as chairman and CEO. “He came and brought a lot of money into the digital upgrade [of the organization], and added a youthful face to the work of the NAACP.”

But his tenure was not without controversy. In 2010, Jealous called for the firing of Shirley Sherrod, a U.S. Department of Agriculture official who was the focus of a viral video released by Breitbart in which she told a story about discriminating against a white farmer. Once the full video was released, it became clear that the point of Sherrod’s story was the exact opposite of what Breitbart had inferred.

“When you make a mistake, you admit it as quickly as possible,” Jealous said. “And you do everything you can to make it right.” Jealous says that he and Sherrod have since reconciled, and that she’s supporting his campaign. “Shirley and I are a couple of organizers who are both slow to anger and quick to forgive. And I’m grateful that she forgave me, and I’m honored to have her support for this race.” Sherrod confirmed that she and Jealous had reconciled.

After leaving the NAACP, Jealous became a partner at Kapor Capital, an investment firm that provides funding for tech startups that serve low-income and minority communities. Its portfolio includes companies like Pigeonly, which makes an app that helps families with loved ones in prison avoid the outrageously high cost of phone calls, and LendUp, which gives people a way to borrow money without relying on predatory lenders.

“He’s an incredibly quick study,” said Mitchell Kapor, the firm’s founder. “He has the leadership experience, he had the organizational experience, he knows the issues. What he hadn’t done previously is invest in for-profit startups.” His role as an investor for Kapor has also provided Jealous with one of his favorite lines, that Republicans will “call me a socialist, but I’m a venture capitalist.”

If Jealous wins, his administration will be the first experiment in merging the Democratic Party’s warring impulses—socially conscious capitalism and social democracy. While Hogan’s approval numbers are high now, his 2014 election, when Hogan defeated then-Lieutenant Governor Anthony Brown by 66,000 votes, was a close race.

“The 2014 election was the lowest turnout in the history of party politics in Maryland back to 1867, the lowest turnout of Democratic voters in the history of the state,” Willis, the former Maryland secretary of state, said. “It’s not going to be the lowest again. You’re going to have a different electorate. Hogan could get every single vote he got in 2014 and still lose by 100,000 votes.”

The remaining question, however, is whether Maryland Democratic voters like Jealous’s stories enough to vote for him—first in the primary, and then in the general election. Despite the lively reception for Jealous and Chappelle at Morgan State—during which a campaign aide led the crowd in chants of “I believe that we will win!”—several voters I spoke to were still undecided.

At the Lutheran church in Catonsville, an elderly woman asked Jealous, “What are you going to do about the schools?” Her voice cracked as she said she didn’t want to hear about removing doors from schools, or about transparent plastic backpacks.

In response, Jealous noted that he had two relatives who had been shot, and vowed to ban assault weapons in the state. But he didn’t specifically elaborate on a plan for dealing with school shootings.

After the meeting, I asked the woman, who gave her name as Anne, what she thought of Jealous’s answer.

She put her hand to her chest and looked up, thinking.

“I don’t feel like he answered the question.”

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