So, Jealous rode a converted school bus to Western High School in Baltimore, a formerly all-white school that his mother helped integrate as a teenager 63 years ago.

AD

“I’m running with the impatience of a child of a woman who sued Western High School for Girls, and knows that the work is undone,” he said at the morning news conference. “I’m running as a civil rights leader who is absolutely committed to finishing the work that began here generations ago, and making sure that every school is fully funded.”

Jealous, 45, has approached his long-shot bid to become Maryland’s first black governor with an inherited sense of duty to expand opportunity, protect civil rights and end poverty. His maternal great-great-grandfather, Edward David Bland, was born a slave and went on to become a Virginia state delegate. The family’s five-generation membership in the NAACP started decades before Jealous became the organization’s youngest-ever president — a job that put him in the sights of extremist groups and led to threats against him.

Little known to Maryland voters, having lived in the state for six years, Jealous vaulted over five challengers in the Democratic primary, none of whom had much in the way of money or name recognition either. Jealous, who would be Maryland’s first black governor, was buoyed by support from major labor unions, backers of Sen. Bernie Sanders (I-Vt.), prominent celebrities and national Democratic leaders.

AD

AD

But in the general-election campaign, taking on a well-liked and well-heeled incumbent, Jealous has floundered, making missteps on the campaign trail and struggling to get his message out and build support from the state’s more centrist Democratic establishment and moderate-leaning voters.

To those who say that his plans — including big boosts in school funding and renewable energy — are too costly, he says the state must invest more in education and the environment now or pay more later. To those who say that Hogan is unbeatable, he points to the state’s 2-to-1 Democratic voter registration advantage and his plan to get historic numbers of Marylanders to the polls.

“My entire life has been uphill: I’m a black guy who was born an epileptic, with a stutter, from a marriage that was against the law,” said Jealous, whose mother and father moved from Baltimore to California because interracial marriages were illegal in Maryland. “I’m an organizer. I was trained to never let a politician’s opinion of what was possible get in the way of the opinion of people who say what is necessary.”

'Justice and opportunity'

When other first-grade boys worried about which game to play at recess at Robert H. Down Elementary in Pacific Grove, Calif., Jealous was launching his first civil rights action. He asked his school librarian why the only books about black people were on Harriet Tubman, whom he called “the train lady,” and George Washington Carver, known as the “peanut butter guy.”

AD

AD

“I was annoyed,” Jealous recalled. “That librarian will tell you she became an expert in children’s literature diversity because of me.”

At 14, his father took him to an organizing meeting for Jesse Jackson’s presidential bid, and Jealous volunteered to help get out the vote.

He led demonstrations against South African apartheid at Columbia University; joined a young Stacey Abrams (who is now vying to become the first black governor of Georgia) to protest a Republican governor’s effort to shutter a historically black college in Mississippi; then won a Rhodes scholarship to the University of Oxford in England.

After a decade working for black newspapers, Amnesty International and a California-based group that finances projects to help low-income families, he took the helm of the NAACP in 2008.

AD

AD

Commentator Van Jones, a friend for 25 years, says he can’t recall a moment when Jealous was not “talking about and thinking about justice and opportunity for folk, and not just black folk, as important as that is. Ben Jealous was fighting for LGBTQ rights when that was unpopular, when it wasn’t trending.”

Jealous is credited with raising the NAACP’s profile, pushing the organization to address the issues of the moment. No more symbolic funerals for the n-word. Instead, the organization was taking on the tea party, reaching out to the LGBT community and expanding the voter rolls by texting young people to remind them to vote.

As president, Jealous focused on state-level activism, rallying with Gov. Martin O’Malley (D) to abolish Maryland’s death penalty, protesting “stop-and-frisk” policies in New York City and traveling to Maine to support a prison-based NAACP chapter that is one of the organization’s only predominantly white affiliates.

AD

AD

“I was not one that voted for him when he came in, but he proved to me that he was worthy of doing the job,” said James W. Crowell III, a board member from Mississippi who was skeptical of Jealous’s age and inexperience. “He was a very hard worker, and I thought he had a good mind to develop new projects and move forward.”

Under pressure

Traveling 145 days a year and fielding death threats, Jealous says he began to rethink his future at the NAACP during the summer of 2013, soon after the acquittal of George Zimmerman in the fatal shooting of Trayvon Martin, an unarmed black teenager in Florida.

Jealous’s marriage was suffering, and his health was deteriorating. When a 30-year-old staff member went into cardiac arrest, Jealous rushed to the hospital. Sitting in the cardiac ward, Jealous said, he thought about his own upcoming doctor’s appointment, and his grandfather, who died of a heart attack at 43.

“I had been told, ‘You look like him, you have the same body type as him, you work as hard as him,’ ” Jealous said. “There’s always the implication of, ‘Be careful not to suffer the same fate.’ And here I was with out-of-control blood pressure, kind of right on time to die.”

Even though he was just one year into a three-year contract extension, Jealous decided to step down. “I remember my conversation with Clarence Page. I called to tell him I was leaving. I said ‘family reasons,’ ” Jealous said, referring to the nationally syndicated black columnist. “He said, ‘Brother, please don’t say that. Give me any other reason.’ I said, ‘Well, Clarence, the problem is, to give you a better reason I would have to lie.’ ”

AD

AD

His announcement in September that he would depart by year’s end was a blow to the NAACP’s fundraising, said Roger Vann, whom Jealous had installed as chief operating officer in 2010. “Ben was an extraordinary fundraiser,” Vann said. After Jealous’s announcement, donors began “playing wait and see.” That year’s fourth quarter, normally a high point for fundraising, was disappointing.

Jealous, who would separate from his wife the next winter and get a divorce a year later, said he felt he had no other choice.

“I needed to save my life. I needed to leave to save my marriage,” he said. “I’m sad I only succeeded at one of those.”

The next move for Jealous was unclear. He told his friends Freada Kapor Klein and Mitch Kapor, whom he had recruited as major NAACP donors, that he was considering joining some corporate boards. Maybe even going to business school.

AD

AD

Kapor proposed a different option: that Jealous spend a day a week at Kapor Capital, his socially conscious venture capital firm, looking at the possible intersections of entre­pre­neur­ship and social justice.

“He didn’t have a business background. I thought there were better ways to get that experience,” Kapor said.

Jealous ended up opening and heading the firm’s Baltimore office, and spent the next five years identifying companies that needed seed money or were running into other roadblocks getting off the ground.

They included Pigeonly, a Las Vegas-based company started by three men who were formerly incarcerated; Allovue, a software company that helps educators allocate resources for students equitably; and Emocha Mobile Health, a company that uses video technology to ensure high-risk patients take their medication.

AD

AD

One of the first Kapor businesses he worked with was LendUp, a California-based firm that was fined millions after state and federal regulators found that it misled customers about its loans. The company says it regrets the missteps and has resolved the issues.

Jealous made $1.2 million from 2015 to 2017, according to summaries of his tax returns. That includes his work at Kapor and about $268,000 in teaching and speaking fees.

Deciding to run

While at Kapor, he began considering a run for public office. The idea crystallized in a Baltimore church basement in 2015, when Jealous was talking to young black men anguished over the death of Freddie Gray in police custody.

Jealous became a surrogate for Sanders’s presidential campaign, chairing his effort in Maryland. By early 2017, after President Trump’s win, he decided to become a candidate himself.

AD

Rey Ramsey, a friend who runs a D.C. investment firm, remembers when Jealous called to tell him that he was planning to run for governor.

“I kept saying ‘Are you sure?’ ” Ramsey said. “I was talking about the unfun stuff, the fundraising, the getting in front of people. I’m trying to get him to talk about strategy. He kept talking about policy, all the things he wanted to do.”

Jealous found himself in a fight like no other — one that analysts said is partly of his own making. He cursed at a reporter during a news conference, lost a chance for multiple debates with Hogan, and missed multiple opportunities to reach out to elected Democrats in Maryland who were not already on his team. Some said he never called them. Others said Jealous’s decision to snub an annual summer political conference sent a message that he did not want or need their help. So they didn’t feel obliged to give it.

Lacking money to respond to ads from Hogan and national GOP groups, Jealous has struggled to introduce voters to his progressive campaign platform: single-payer health care, a $15 minimum wage, trimming sales tax from 6 percent to 5.75 percent, expanding the use of renewable energy to 100 percent and boosting teacher pay by 29 percent over seven years.

Hours after his news conference at Western High, Jealous traveled to an office building in College Park, Md., for a “telephone town hall” with Sen. Cory Booker (D-N.J.) — an inexpensive way to get his message out to voters, hammering Hogan on rising health-care costs, lackluster job growth and declining school ratings and explaining what he would do instead.

In response to a question about criminal justice reform, he spoke directly to Booker, who was seated next to him at a conference table in a small makeshift office with voting maps and campaign signs on the walls.

“We came of age where our generation was the most incarcerated on the planet and the most murdered in the country,” Jealous said, before explaining his goal of slashing the prison population and using the savings to make college more affordable. “And you and I have spent our entire lives trying to get our country to a better place, our community to a better place.”

He ended the call with 1,200 Prince George’s County voters on the line, talking about health-care costs and his plan to pay for universal prekindergarten by legalizing and taxing marijuana.

“We don’t need to accept Republicans gently pushing us back in Maryland,” Jealous said later, in an interview. “We did it on civil rights. We can do it on education, the economy and the environment. That’s what gets me out of bed in the morning. . . . It’s the same thing that got my grandma out of the bed as an organizer.”

Next: Maryland Gov. Larry Hogan (R).