KAREN CALDICOTT

On a crisp Sunday morning in February, Benjamin Jealous–the president and CEO of the NAACP–stepped out of a yellow cab and made his way into Harlem’s storied Abyssinian Baptist Church. He was accompanied by an assistant and a church emissary assigned to shepherd Jealous to the offices of Abyssinian’s patriarch, the Rev. Calvin Butts. This was no mean feat. As Jealous walked in, right hands were extended all around, eager to press flesh.

At 36, Jealous is the youngest person ever to head the NAACP. It’s a subtle nod to the hip-hop generation, a fact that seems to amaze everyone except Jealous, who hasn’t had much time to rest on accolades. Since taking over the NAACP last September, he’s been charged with the work of the philosopher and the yeoman. On the one hand, he’s had to grapple with the purpose and mission of a civil rights organization in the age of Obama. On the other, he’s been tasked with improving the NAACP’s membership, finances and stability. Three of its last four leaders have left under a cloud of controversy, leaving even some allies wondering about the organization’s fate. So when Jealous arrived for his meeting with Butts, it was not simply a social call for two civil rights leaders from two different generations but an act of restoration.

Butts, who’s been ministering at Abyssinian since before Jealous was born, shook the younger man’s hand and offered him a seat. Abyssinian is one of black America’s most famous churches. It was the seat of power for Adam Clayton Powell Jr., and its services inspired Dietrich Bonhoeffer, the German pastor and Nazi resister who conspired to assassinate Hitler.

As it happens, the NAACP was in the midst of its 100th anniversary observance, and Abyssinian was in the midst of its 200th. But Butts explained that Abyssinian and the NAACP had been at loggerheads for more than fifteen years because of the actions of Jealous’s predecessors. “The last NAACP president to speak from our pulpit was Benjamin Hooks,” Butts said. “We tried to keep up a steady relationship. We were very involved. But a member got very angry with Ben Chavis.”

Jealous nodded politely and thanked Butts for the chance to address his congregation. Butts adjusted his clothes and readied his robe for the service. His office was sprawling and gorgeous. There was a large wooden desk and portraits of Kwame Nkrumah, Adam Clayton Powell Jr. and Malcolm X. There was a knock at the door, and an assistant pastor stepped in to tell the men that the time for morning service had arrived.

Jealous and the processional of church nobles were shuttled downstairs. He sat in the first row, joined by his wife and family. When Butts invited him up to speak, he ushered Jealous to a microphone in front (only preachers are granted the privilege of the pulpit). Jealous looked out and smiled and invoked the history of the NAACP, Abyssinian and the country at large.

“We would not be 100 if you weren’t 200,” he said. “I’m here like most of you with my head in the clouds of January 20, the day we broke down the color barrier at the White House, but with my feet firmly planted in January 21. My generation was told that all the great battles were over. And we emerged the most murdered people in the country, and the most incarcerated group on the planet.”

Jealous finished his speech to broad applause and took a seat next to his family. “Thank you, brother Jealous,” said Butts. “You’re off to a great start.”

Jealous is stocky and over six feet tall. His high-pitched voice is at odds with his stone-serious face. When he laughs, it almost comes as a surprise. His skin is light enough that in the early ’90s, when he worked as a reporter and managing editor for the Jackson Advocate, Mississippi’s oldest black newspaper, he occasionally passed for white, digging for information beyond the reach of his colleagues. His father is the scion of a prominent white New England family whose ancestors fought at Bunker Hill. Archibald Willard, who painted The Spirit of ’76, is a distant cousin. His mother’s family traces its ties back to a plantation, and the men in her family were dignitaries during Reconstruction. Despite his lineage, Jealous is tenaciously black and takes unkindly to being called biracial.

“In my family, race and heritage are two different things,” says Jealous. “My dad was clear that if he married a black woman, he’d have a black child. That was the law. But there was also a sense, on both sides of the family, that we are American.”

Jealous grew up in Monterey, California, but spent a lot of time in Baltimore, where his mother was raised. His household was a bubbling caldron of politics, debate and history. Jealous’s maternal grandmother would recount for him oral histories of his family’s struggles under slavery and Jim Crow. Robert Watts, Baltimore’s pioneering civil rights jurist, was a family friend. From the time Jealous was 4, Watts would greet him by asking, “Son, what are you prepared to argue about?”

Well, as it turned out, plenty.

Jealous lodged his first protests in first grade, over the lack of books about black history in the school library. “I never liked fairy tales. I always liked history,” he recalls. “I read a lot of books themed around the bicentennial. I read all the books on my dad’s family. And then I asked, ‘Do you have any on my mom’s family? Not the railroad slave or the peanut butter guy.’ The librarian was stumped.”

When Jealous was 13, he attended the birthday party of the son of McGeorge Bundy, former national security adviser to John Kennedy and Lyndon Johnson. “My first phrase was ‘What were you thinking when you planned the Bay of Pigs invasion?'” recalls Jealous. “He said, ‘You know, son, I’d rather not talk about that right now…'”

By the time Jealous was 16, he was registering voters for the NAACP. At Columbia, where Jealous went to college, he continued in the family tradition but with a kind of privileged bent that’s rarely seen in black activists. When Jealous was 18, he was stopped on Columbia’s campus by an FBI officer who mistook him for an Iraqi student. (Jealous had spent the previous week protesting the Gulf War.)

“I went off on him about why I looked the way I looked,” says Jealous, referring to his ancestry. “That was the moment where I really realized I had ownership in this country. And for him to suggest that I didn’t belong here… I went off.”

This sense of ownership in America reflects the New England origins of his family, but just as important it reflects the willingness of his grandmother to discuss slavery and other aspects of the black past that older generations of African-Americans tried to forget.

In his junior year of college, Jealous led a demonstration to preserve Columbia’s scholarship program for students of color. He climbed through a window of Low Memorial Hall to disrupt a board of trustees meeting and stage a sit-in, for which he was kicked out of school.

Jealous then headed to Mississippi and set his mind on acquiring some work experience. At the Jackson Advocate, he stayed true to the paper’s name and was as much an activist as he was a reporter. He investigated the state prison system. He fought the effort to shrink Mississippi’s historically black colleges. In his early 20s, he became the Advocate‘s managing editor. Later he returned to New York; Columbia had readmitted him. A year after he left the Advocate, it was firebombed, allegedly by white supremacists.

Jealous went on to become a Rhodes scholar, earning his master’s degree in comparative social research. He continued his reporter-activist work as head of the National Newspaper Publishers Association, a consortium of black newspapers around the country. He worked at Amnesty International USA pushing Congressional efforts to ban prison rape and racial profiling in the wake of September 11. He returned to California and served as president of the Rosenberg Foundation, which funds economic inclusion and human rights grants in California. By the time Jealous came before the NAACP board seeking its presidency in 2008, he was following the path he had started walking decades earlier with his childhood protest of his school library.

“I had known him slightly before he applied,” says chairman of the board Julian Bond. “[When he] came into the room I was pleasantly surprised and taken aback with both his background registering voters when he was too young to vote himself and the fact that every professional job he’s had related to what we do. He had experience in the nonprofit world. He just seemed to fit. His age was an asset. It just struck me that he was the perfect package.”

The NAACP board was somewhat less impressed. Jealous’s resume–stints working for the black press, executing grants for nonprofits, lobbying for human rights–was standard for a social activist. But by the lights of the NAACP’s recent history, Jealous’s professional biography was peculiar and lacking. He had not pastored a church, he had held no elected office and he had no direct ties to the civil rights movement.

Jealous’s candidacy was met with skepticism on everything from his experience to his skin tone. “That’s been our buttress, our hope and our faith–the black church,” NAACP board member Amos Brown told the Christian Science Monitor. “However, under the leadership of Julian Bond, that relationship has been shattered, ignored and fractured…. You are going to bring someone on board who can’t inspire somebody?… He hasn’t led no movement, he hasn’t led no cause where black folks can say, ‘This is where the man was.’ A leader is out front where the people can see him. Nobody knows Benjamin Jealous.”

The board ultimately split 34 to 21 in Jealous’s favor. But his reward was a mixed bag. The NAACP, as a social justice organization, had tremendous clout. But for the past two decades it had mostly been led by a succession of unsteady leaders. Benjamin Chavis followed the esteemed Benjamin Hooks in 1993 and plotted to steer the NAACP toward a younger generation. But Chavis was forced out a year later after he was found to have used NAACP funds to settle a sexual harassment suit. He was followed by Myrlie Evers (widow of Medgar Evers), seen as a stabilizing force. She in turn was followed by Kweisi Mfume, whose tenure ended in 2004 amid accusations of sexual impropriety (it was alleged that Mfume rewarded sexual partners with plum jobs). Jealous’s predecessor, Bruce Gordon, lasted just nineteen months.

Moreover, when Jealous was handed the reins, the NAACP was in its third year of having to dip into its endowment to continue operations. In 2007 the group laid off more than a third of its staff and closed several regional offices. And beyond the nuts-and-bolts problems, the NAACP was in the midst of the latest flare-up of an existential crisis that has haunted it since the days of W.E.B. Du Bois, its founder, one that has become more acute in the era of Obama.

The NAACP made its name by tackling the structural arms of white supremacy–segregation, job and housing discrimination, disenfranchisement. Its favored arsenal was not the direct action of Martin Luther King Jr. but the jurisprudence of Charles Hamilton Houston and Thurgood Marshall.

“The NAACP was historically averse to public demonstrations,” says historian and Du Bois biographer David Levering Lewis. “It preferred galas, social events, tithing its members. The idea of marching and voluntarily being incarcerated was alien and to a large degree anathema. This is not because of a lack of personal conviction or courage. The idea was, the best way to change society was collaboration.”

The NAACP’s focus on collaboration led to several splits over the years, most famously between Du Bois and Walter White. Du Bois, tired of the seemingly endless fights for integration, embraced separation for African-Americans and a focus on improving the black community. White pressed for integration; he ultimately prevailed, and Du Bois left the organization. But that basic conflict of practical community reform versus moral national reform has often plagued the NAACP internally and been invoked by its critics externally.

The criticism has assumed new life in the post-civil rights era. As the vestiges of white supremacy have fallen away, in large measure because of the NAACP’s efforts, blacks have grown more concerned about the achievement gap, violence in their communities and fatherlessness. But the NAACP has remained focused almost entirely on its core civil rights agenda–at times to the chagrin of its membership.

When Gordon came to the helm, he envisioned a program to make the NAACP more relevant by tackling new problems like the dropout rate, the plight of black men and HIV awareness. But Gordon ran into stiff opposition from NAACP officials, Bond chief among them, who feared that the group was moving away from social justice and into “social service.” A year and a half after he was brought on board, Gordon, who did not respond to inquiries for this article, resigned.

“I think people generally like social service,” says Bond. “White, black, liberal, conservative, they all like social service–Habitat for Humanity, for instance. It can be done quickly, whereas social justice can take years. There’s nothing wrong with social service. But we are one of the few organizations focusing on social justice.”

Given his youth and his history of confrontations with power, one might think Jealous would strike a pose more radical than Bond’s. That would be a mistake. “We’re motivated by the problems facing the black community, but our goal is a fully functioning democracy,” Jealous says. “Our goal is a government that works for everybody. If the government worked better, we wouldn’t need many of these services.”

“The reality is that you can leverage way more change out of federal government, state government, even a county government, than you can leverage charitable dollars to solve those problems,” says Jealous. “In fact, many of those problems you can’t even solve with charitable dollars…. I’m talking about mass incarceration, for instance.”

Jealous and Bond essentially argue that the only legitimate avenue for social change is government policy–hence the notion that if the government worked right, “social service” would be unnecessary. Post-civil rights African-Americans have grown increasingly impatient with this line of thinking. The weakness in the NAACP’s perspective is that it depends on a sympathetic government ear. The NAACP’s victory in Brown v. Board of Education, for example, was the result of some brilliant legal arguments, but it was also the result of a court willing to listen. In the wake of the conservative counterrevolution, the NAACP hasn’t been able to count on that sort of sympathy.

Despite a few flirtations with change, the NAACP never altered its strategy. Thus, while it persisted in advocating for a fully functioning democracy, blacks continued to suffer. For African-Americans who push for some kind of community-based approach to tackle violence in their community or to close the achievement gap, the NAACP has had little to say.

Even in areas where the NAACP has traditionally had a presence, its reputation has been eroded by broader changes in society and among African-Americans. In the era of Facebook and Twitter, it’s not clear that one messianic figure or one organization can articulate the concerns of millions. Indeed, the millions are more likely to simply do it themselves. “When people needed to organize for the Jena Six, they did it themselves,” says cultural critic Mark Anthony Neal. “Their first choice wasn’t the NAACP.”

The NAACP is, in some ways, boxed in by its very name. If an association claims as its mission the “advancement of colored people,” people expect the group not to get hung up on tactics. Jealous believes that the NAACP can address certain issues better that it has ignored in the past–HIV awareness, for instance. But for all his youth and idiosyncrasies, his basic outlook on the NAACP’s mission is very traditional.

“There’s a lot of people out there who would like to see the NAACP as some sort of alternative government or government service provider for black people,” Jealous says. “That’s exactly what we’ve been fighting against for a century.”

But living in a new century, the fight may have to change.