Credit: Photo by Darrow Montgomery

With slicked back hair and a dapper sport coat, Courtland Milloy could be confused for a preacher. Which, in some ways, he is: Blatantly reproachful from his pulpit—which just happens to be a Metro section column in The Washington Post—he’s demure and polite in person.

Milloy’s surprisingly tender flock-tending style is on display as he chats people up one November afternoon at the Children of Mine Youth Center in Anacostia. Kids from the center, a visiting lawyer, some Maryland Episcopalians picking up trash—they all get taken in by the man with the good-natured baritone that cracks and squeaks whenever he laughs.

Milloy listens raptly, wrinkles deepening. A handsome, straight-featured black man, he shows no hint of writerly condescension as he works a room full of all those ordinary citizens that media strategists are so perpetually keen on reaching. At moments like this, you’d never guess how ruthless Milloy’s dark side can be. While some kids shoot a sleepy game of basketball on the center’s colorful asphalt court, the 59-year-old gets the lowdown from Hannah Hawkins. Back in the 1990s, in order to feed the children of Southeast, Hawkins chased raccoons and homeless men from a house at 2263 Mount View Place SE, allowing her to move her nascent program there. Now, to feed more children, Hawkins says she needs to expand. She needs to renovate an adjacent and dilapidated house on the property grounds.

Milloy has declared he’s working on a column about the center. He isn’t taking notes, though.

“I’m just here to get a feel for the place,” he says. It doesn’t matter anyway; the most significant exchange to happen that day will be easy to remember. It’s when Milloy asks Hawkins how much she needs for the renovations. “I could do it with $7 million,” she replies. The writer doesn’t flinch. After thinking about it for a while, Hawkins decides she could do with more: Ten million.

A Milloy column could help some of that money materialize. For the last 27 years, his work has highlighted black life in the District. Milloy can bring attention to a problem, which can lead to dollars in the form of donations and city money. The potential chain reaction leads local social worker and activist Ella McCall to call Milloy whenever she sees a dire need emerging. “You’re my mouthpiece,” she’s told him.

Milloy insists he’s no such thing. But if he’s not quite a mouthpiece for a black agenda in the District, he’s the closest thing to it at the Post—or anywhere else in the local mainstream media, for that matter. Milloy’s column cuts against the usual conventional wisdom in journalism these days, giving readers a mirror of an urban, poor D.C. instead of the wealthy suburbs advertisers would probably prefer. And while the newspaper lavishes attention on its new iPad incarnation, and courts Facebook and Twitter like a desperate teenaged boy chasing after a crush, Milloy almost gleefully stays away from the trend.

Like the late Herb Caen in San Francisco, he’s an old-school journalist doing an old-school job: the Metro columnist writing about, and for, the city’s downtrodden. For decades, that was a generally quiet, low-impact job. But following a mayoral campaign that pitted rich against poor in dramatic new ways this fall, Milloy’s knack for reducing post-modern problems to their race-and-class roots has suddenly made him a controversial, buzz-generating columnist—the man that the supposedly liberal class of newcomers to D.C.’s gentrifying neighborhoods love to hate.

In the steadfastly non-gentrified neighborhoods that Milloy covers, though, he’s rarely seen as incendiary. Community broadcast journalist Jerry Phillips, who’s known the columnist since the 1970s, says Milloy is basically a black Norman Rockwell. “Norman Rockwell always had a subject that was American in some way,” he says. Milloy writes the story of America, “but for the black community.”

“The District of Columbia doesn’t care about me,” Hawkins half shouts while taking a walk around the building so she can show off the center’s small vegetable garden to Milloy. She senses that if she has any hope of airing that accusation, Milloy is her guy.

The city has been growing less interested in what people like Hawkins—people fighting for “quality of life” in places where that means more than bike racks—are up to. But Milloy is. Even though there’s nothing coming up in it, Milloy gazes at the garden’s dirt mounds a long time and manages some reverential awe.

Here’s the official national narrative about Washington, D.C., in 2010: Mayor Adrian Fenty was ousted in large part thanks to the bold reforms exemplified by his public schools chancellor, Michelle Rhee. It’s not hard to find examples of the narrative, which holds sway in magazines like The Atlantic and The New Republic, not to mention the editorial page of the Post.

The Post, as it happens, is also home to the official counter-narrative, though you’ll have to look harder to find it: Its most prominent platform is on page B1, where Milloy has a contract for a single weekly column. He writes more when he’s moved, which, this fall, was often. In Milloy’s telling, Fenty and Rhee were villains who closed down black-majority schools and heedlessly sacked black teachers and bureaucrats.

Milloy’s column was about the only place where many white Washingtonians even encountered that narrative, which reached its apotheosis in a scathing post-election column headlined “Ding-dong, Fenty’s gone. The wicked mayor is gone.” Reveling in his schadenfreude, Milloy expounded on his theory as to why Fenty bit it. “In a stunning repudiation of divisive, autocratic leadership, District residents Tuesday toppled the city’s ruling troika: Mayor Adrian Fenty, Attorney General Peter Nickles and Schools Chancellor Michelle Rhee. All busted up,” he wrote in a column that quickly went viral. “The trio’s contempt for everyday people was handed back to them in spades at the polls.”

Of course, Milloy wasn’t eligible to vote against Fenty himself: He lives in Fort Washington, in Prince George’s County. All the same, he was the first major writer to play up racial voting dynamics that most of Washington could sense—but didn’t dare articulate—well ahead of election day. Milloy accused Fenty of catering to the privileged. He also took aim at Fenty supporters, coining a phrase readers are unlikely to forget anytime soon. After recounting Fenty’s refusal to meet with Dorothy Height and Maya Angelou, Milloy tore into Fenty-ites who might not recognize the importance of such a gesture.

“Watch them at the chic new eateries,” Milloy wrote. “Fenty’s hip newly arrived ‘creative class’ firing up their ‘social media’ networks whenever he’s under attack: Why should the mayor have to stop his work just to meet with some old biddies, they tweet. Who cares if the mayor is arrogant as long as he gets the job done? Myopic little twits.”

“Myopic little twits” seemed like code (barely coded code, at that) for young, white gentrifiers, and Milloy got gigabytes of angry e-mails that assumed as much. “On behalf of all young white new residents to the District—thanks for making us feel so welcome!” one furious note read. “Let me clue you in to something. We’re not leaving. We are her[e] to stay because we like this city and we’re only going to become more involved.”

But where the hundreds of irate comments clogged the Post’s website following the publication of Milloy’s “Ding, Dong” column were testimony to his having struck a nerve, the local blogosphere’s reaction was a bit different: Milloy, the myopic twits argued, was yesterday’s man.

“The column goes so much further than legitimate political criticism allows, depicting an author with an apparent desire to re-inject a culture of divisiveness back into the city,” wrote editor Aaron Morrissey. And why would he do that? “I don’t know if ‘offensive’ is the right word for it. He’s a columnist, and his job is to churn up reactions. It just struck me as being a little out of touch.”

Adam Serwer, a D.C.-bred American Prospect writer and frequent Twitter presence, argued that Milloy’s “divisiveness” was a red herring: “It’s important to note that Gray never talked like this, even if some of his supporters did,” Serwer wrote. On the phone, Serwer, who’s biracial, explains that Milloy had dragged race into something that was primarily about economics. Serwer figures high unemployment rates led to Fenty’s undoing, not the snubbing of venerated black women. Why overstate racial resentment? “He sort of represents a certain kind of establishment perspective.”

Once upon a time, Milloy was the young writer using terms like “out of touch” and “establishment perspective” to describe his targets. That those words are now being used to describe him is perhaps a clue as to how much things have changed since the days of community uprisings and disco. Talking to Milloy, and reading his column, the rhetoric feels a bit dated—right down to the undercurrent of college Marxism. “Troika?”

Talk to Milloy about the state of the media and his cranky-old-uncle schtick becomes even more apparent. “Sounds perverted,” he gripes when asked about Twitter, his voice suddenly mockingly high: “Follow me on Twitter, and watch me tweet…”

“There was some anger,” Milloy says of his September columns. “There was [also] some, ‘Thank you for putting into words what I’ve been thinking.’” Those who gave Milloy a thumbs-up on his screed were likely frustrated with Fenty’s administration.

But as a national narrative coalesced about how the forces of race and gentrification had undone the District’s reformist mayor, Milloy came off like Chocolate City’s version of Glenn Beck. In Milloy’s view, the story bouncing around was that D.C. had no idea what was good for it. Fenty had tried to change things for the better, only to be thwarted by blacks too resentful of the District’s influx of white residents to realize how essential the mayor was to a better future. In this version, Milloy and those who thought like him were a mirror image of the Tea Party. Issues had been ginned up, but at their base was racial anxiety. In other words, Milloy and his supporters were nothing but bigots.

And, like the other Tea Partiers, they faced a backlash: Six weeks later, write-ins captured nearly a quarter of the city’s general election votes. It’s a good bet that wouldn’t have happened without the post-primary racial agita that began with Milloy’s column.

Milloy arrived in the District in 1974 after two years at The Miami Herald. He was 23 years old, without a job but sure he’d find one. He camped out in The Washington Post’s lobby for a day. He was hoping to meet the editor in charge of recruiting, Elsie Carper. Milloy had neither an appointment nor any idea what she looked like.

Growing up in Shreveport, La., in the 1960s, Milloy felt his destiny was to become a journalist. Though he has bitter memories of enduring discrimination and racism, his upbringing was auspicious. His parents were both teachers: His father taught journalism and his mother typing. “These two things made for a calling, don’t you think?” Milloy asks. When he was old enough to attend Booker T. Washington, the revered black high school where his parents worked, he joined the school newspaper and began writing a column. When he gave one of his columns the headline, “The Cure for Boredom in the Classroom,” he learned what it was like to be at the center of controversy. “It created a buzz,” he remembers. “I’d never created a buzz before.”

From there, Milloy headed to Southern Illinois University in Carbondale, Ill. After college, he scored the job at the Herald, but he knew he wasn’t staying. He was anxious to leave the South behind, to live in a place that had an energy and potential that matched his own. Big newspapers were starting to hire more black reporters, prompted in part by the civil rights struggle they’d been chronicling in their own pages. Milloy figured he’d try the Post.

During the hours he lurked in the paper’s stolid lobby, Milloy befriended a security guard. At the end of the day, Carper came through the lobby and made a beeline for the exit. The security guard pointed her out. Milloy talked fast. A few months later, he was working for the newspaper that was toppling a president. Milloy’s beat was somewhat less glamorous: He’d be covering “cops and courts” in Prince George’s County.

Milloy found himself a part of a small group of rising black Washington journalists. “Courtland came along at a time when media opened its doors to black employment,” says Phillips. His peers were people like Maureen Bunyan, Kojo Nnamdi and Juan Williams. According to Phillips, it wasn’t uncommon for black reporters to run into each other at a private club called the Fox Trap, at the corner of 16th and R streets NW.

It could be a pretty wild scene, but Courtland was reserved: “A typical newspaper guy,” recalls Phillips. Milloy’s friend and onetime Post colleague Richard Prince remembers him as “balanced.” Prince was known for opening his Dupont Circle house up for late-night get-togethers that catered to the black media elite. Milloy was often in attendance, and always friendly, but definitely not a party animal.

Milloy’s temperament kept it hidden, but he did have a wild side, and slowly, it began getting the best of him. By 1988, he’d been sucked into a spiral of drugs and alcohol. “You wind down after one of those days on deadline,” he remembers. But as quietly as Milloy slipped downhill, he surged back. “The time came when my party was over,” he says. “When you’re like that, it’s hard to be creative.”

Milloy never talked much about his addiction, and it might have stayed a secret if not for Marion Barry. At a Post luncheon in 1994, Barry, campaigning for mayor, was speaking about his own drug and alcohol use as Milloy sat by, listening. When asked to name the major mistakes he’d made Barry digressed. “Before we get to that, let me just talk about myself a little bit, personally. Again, I think I’ve had a remarkable recovery…I often use the example of [WRC-TV’s] Jim Vance and, I hope he doesn’t get offended by this, Courtland Milloy, who’ve gone through difficult situations but come back to work.”

In a July 3, 1994, column (“Barry’s Healing Example”), Milloy tried to come to peace with suddenly being lumped in with the politician whose own drug use led to the immortal line, “Bitch set me up.”

“Whether any of his political fixes or financial remedies would work, I couldn’t say.” wrote Milloy of Barry’s lunch interview. “But it did sound like he had found a solution to the problem of alcoholism and drug addiction. And what he had to say about a spiritual path to freedom from the bondage of self was a lifesaver.”

That may have been the closest Milloy would ever come to seeing Barry and himself in the same light. Barry had started his career as a pugnacious activist. Some of those Milloy associated with, like Nnamdi, were involved with the black power movement back in the day. But Milloy never quite took on black nationalist politics.

By the late 1970s, Milloy’s beat had shifted from Prince George’s County into the District, and he gained a reputation for knowing its streets better than anyone else. In 1981, when the veracity of a Pulitzer Prize-winning story by Janet Cooke came into question, editors turned to Milloy for help. Cooke, another young, black reporter, had embarrassed the Barry administration with “Jimmy’s World,” a tale of an 8-year-old heroin addict, adrift in the District with no intervention from the authorities. (Barry, hoping to save some face, claimed the boy was known to the city and was receiving treatment.) Inside the Post, some staffers were skeptical of the whole thing. After Cooke won the Pulitzer, former colleagues of hers in Toledo, Ohio, noticed details of her own official biography didn’t match up with what they remembered. Milloy knew all the dark and dangerous places Cooke’s story referred to. “I was asked to go with her to find Jimmy,” he says. When Milloy escorted Cooke to the spots she’d identfied, there was no sign of the drug-addled kid. She’d made him up. Milloy wasn’t surprised: “I just thought it was far-fetched.”

If the Cooke fiasco created any tense racial dynamics, Milloy was insulated. “Most of my immediate editors over the early days were black,” he remembers. “They answered to white people. When I was angry at them I called them middlemen”—he laughs—“operating for the man. But that wasn’t true. That was just my emotional stuff. The fact is I have worked for some of the best editors in the business, and for the most part they were black editors.”

No matter how good they were, Milloy’s black editors found it hard to move up, though. “It’s weird to think that all the time that I’ve been there, there’s never been a black managing editor or a black executive editor,” Milloy says. “And there are complicated reasons for it, but it just hadn’t been the case.”

Being a black columnist at the paper has its own strangeness, especially nowadays, when anger has become a commodity. “In this day and age when page views and comments are, you know, very appealing to advertisers, is that a good thing or a bad thing for people to be [angry]?” Milloy says. “I get disturbed because the reality is a person who makes a comment and calls me a nigger, that’s still an ad man’s click.”

As a reporter, Milloy had often channeled his own observations on race and class into his work. He would, as he puts it, “fight for the cause” in print, even if he never explicitly got into more political forms of engagement. As his career took off at the Post, that was a problem. The features he wrote were saturated with opinion. After wrestling with Milloy’s penchant for spouting off, editor Larry Kramer came up with a solution in 1983.

“So he’d wrangle over each feature I wrote trying to figure out what it was,” Milloy says. “One day, he decided to make life easier on everybody by dropping the disclaimer, making the byline bigger and just calling me a columnist.”

The Metro section columnist mantle Milloy snatched up brought him into contact with the District in a whole new way. Whereas the reporter is the city’s messenger, the columnist is its oracle, expected to convey truths in fits of revelatory ranting. For Milloy, this has meant writing in a jazzy voice that harkens back to a time when such agreeable stylistics might be accompanied by two congas and some incense.

Other columns showcased Milloy’s inner shock jock. In July 1993, he proposed that while attempting to combat AIDS, the city was lending more support to gays and whites than to (presumably straight) blacks. In 1996, he framed D.C.’s steep black homicide rate as white-run genocide. In September 2002, when Anthony Williams was mayor, Milloy accused the black politician of not being able to relate to other black people. And in 2007, Milloy shellacked Fenty for hiring whites as the city’s legal counsel and attorney general.

But like all columnists, he’s struggled with a world changing around him. He hasn’t lived in the District since moving from 8th Street NE to Prince George’s County in 2005, and at times, it shows. Standing outside Children of Mine in Anacostia, Milloy marvels at seeing two white people walk by. “Do you know how many homicides I covered just down the street?” Sometimes, even an oracle is confounded.

Writing about race in racist America was hard enough. Writing about race in “post-racial” America is even tougher. As racism has weakened as an institution, it’s gained strength as a psychological tick. As pernicious and adaptive as any antibiotic resistant germ, this particular social ill is a constant. What keeps changing is the way we talk about it.

The civil rights movement of the 1960s gave way to the black nationalist movement of the 1970s. That led to the affirmative action culture of the 1980s, and then political correctness in the 1990s. But it became apparent that what all of those different strategies were trying to fight was still capable of surviving in various forms. Maybe W.E.B. Du Bois, who allotted an entire century to solving the predicament (“The problem of the 20th century is the problem of the color line”), was low-balling it.

Yes, the country has seen the election of its first black president. But far from proving that the problem of the 21st century is some other demarcation of power, it’s merely turned the page to another chapter in our tortured history of race and language. And if there’s plenty of not-so-covert racial hostility—witness all the rhetoric about Barack Obama’s citizenship and religion—it’s also meant that urban columnists like Milloy find themselves in an unusual position: His major foils, these days, aren’t race-baiting brutes but privileged, usually liberal, whites, members of the new creative class who are distinctly unaccustomed to being cast as anything other than the revitalizers of their adopted neighborhoods.

It’s easy to cast Milloy as a guy stuck in the past. (With a 42-year-old son, from his first marriage, and a 32-year-old stepdaughter and 21-year-old son with his second wife, Milloy certainly starts any conversation with his myopic little twits across a generation gap.) His columns describe D.C. using a racial binary that the District began to shake off long ago as other people of color poured into the city. His monolithic view of the city’s white population ignores the different understandings of space—and the different economic realities—of the younger, just as professional, but not as rich, newcomers who’ve gentrified neighborhoods like Petworth. His rants against Twitter add some comic relief and show that being a technophobic crank knows no race.

But maybe it’s worth holding off on the ironic teasing for a second. In Milloy’s telling, his barbs at D.C.’s creative-class newbies aren’t about lashing out at them because they’re new. He’s lashing out at them because they’re not. As gentrification takes hold of Washington and issues of inequality emerge, it’s not enough to take solace in Obama’s post-racial ideal while neighborhoods acquire a new mono-cultured cast. People who move into changing neighborhoods have a responsibility for what’s going on. Or so Milloy, in his role as the crotchety grandfather they never wanted, wants to tell them.

Milloy sees new Washingtonians as the flip-side of a process that, in his view, involves older ones being pushed out. And if the actual truth behind African-American departures is more complicated—plenty of folks, starting with Milloy, decamped voluntarily—he argues that it’s pretty damned egocentric to imagine that everything is sweetness and light.

“Well, I don’t know why people think I have a problem with the influx itself,” he says. “Not to be deliberately provocative, but that is the white view, it’s white-centered. ‘Why are you opposed to us moving in?’ But nothing about, ‘Why are you concerned about the way black people are being kicked out?’ People are being displaced, and sometimes run over roughshod. To me, that’s the issue. But depending on who gets to frame the issue—who gets to pose the question, set the framework—it becomes, you know, what’s wrong with white people moving in?” (Milloy, of course, is also the one setting the framework, at least once a week in the daily paper.) “Bridging those sorts of perceptual divides becomes very challenging,” he continues. “People become pretty, pretty self-centered when it comes to things like that.”

“I don’t make a racial distinction between people of privilege,” Milloy will later hedge in an e-mail. “All of the haves need to take a look at America’s widening economic divide, and start doing more to help those who have not.”

On a Saturday morning, Milloy and I are sitting in his Acura, parked on a garden-lined street in Capitol Hill. At his suggestion, we’ve fled the clamor of a Pennsylvania Avenue SE Starbucks. As he sips at a to-go cup, Milloy is open and garrulous, so much so that he doesn’t mind bashing the Post a little. (After all, he’s a contract employee now, having taken a buyout a couple of years ago) “The Post used to be a writer’s paper,” he says, arguing that the daily no longer takes risks. He’s dressed in a Hawaiian shirt and jeans, and wearing a pair of Terminator sunglasses.

Maybe what’s got him so talkative is the rounds of tennis he just played at the Southeast Tennis and Learning Center on Mississippi Avenue SE, the same place where Marion Barry likes to whip his racket. Milloy has played against the councilmember, but it’s hard to get through a game, he says, since people are constantly “coming up to Marion.”

As he’s feeling so loose, this seems the opportunity to spring my blunt question on him, the one many of those who took the “myopic twits” column to heart might be aching to ask. “Do you like white people?” I venture.

Milloy’s answer isn’t likely to calm any of the people who sent him those furious e-mails back in September.

“White people… That’s a funny question,” he starts out. “I’m trying to see a creative way to answer that… I could say yes. I could say, ‘Absolutely, man.’ But, you know, like, let’s start with this—I like people. I love people, man. And the fact of the matter is… I have all my life.”

But a tick later, bringing up the recent elections, Milloy gets a little angry. “It makes me go back to the beginning—the country was founded on the premise of white supremacy, blacks were slaves, they couldn’t, they were three-fifths, you know, this was encoded in the law,” he says. “People have a way of feeling that they’re on top, that’s the way these things are set up. The layout of the District of Columbia, the fact that there exists a white wealthy ward at the opposite end of a poor predominantly black ward, did not come up by accident. The city was built by slaves and German, Italian, Irish immigrants for the most part. Only one of those groups didn’t get paid, or get the credit. So does it rankle me sometimes that people don’t want to give black folk credit? Yeah, it does.”

Milloy goes silent for a moment. Just then, a police car pulls up alongside us, and we both tense, seeming to simultaneously realize what we are: Two black men dressed down in an SUV. In a word, suspects. Though the cops move on without incident, the fact that Milloy and I, separated as we are by a generation, had the same, instant reaction, might be a clue as to why Milloy is still relevant: Racism is still a big part of our lives.

Sure, I might wind up tweeting about the stare-down with the cops, and Milloy sure as hell won’t. But until Mayor-elect Vince Gray’s “one city” makes the jump from good concept to daily reality, Milloy may be the best way for black D.C. to vent its frustrations. Milloy provides a kind of tough love Washington shouldn’t want to do without.

“Racial conversations are very hard to have. And I wouldn’t consider [the column] a traditional racial conversation,” says Milloy. “But for me, rough and ragged as it may be, I find that people’s thoughts and expressions on race to be pretty revealing.”