Credit: Photo by Matt Dunn; Illustration by Brooke Hatfield

Most fights among D.C. residents somehow involve parking. So you could argue that David Alpert’s introduction to local political warfare was only typical.

Alpert’s position in the fracas, though, was somewhat unique. Where most Washingtonians tend to kvetch about how difficult it is to snag a street spot, Alpert wanted less parking, not more. Back in 2008, as the District’s Zoning Commission started work on a comprehensive rewrite, Alpert embraced the idea of decreasing the number of parking spots required for new developments.

“That was my first exposure to the antis,” Alpert says, employing his general label for people who oppose change on principle. “Because I went to these meetings, and there were these people, like Barbara Zartman from the Committee of 100. She was there to fight hard for keeping the zoning the way it was, basically, against the efforts of the Office of Planning to upset the apple cart of these prohibitions on lots of things.”

(Photograph by Matt Dunn)

Alpert took to the blog he had started earlier that year, Greater Greater Washington, to launch his counterintuitive counteroffensive. For 10 days, he posted one reason per day why parking minimums were bad: They make housing more expensive and render good commercial development projects unfeasible, he argued. They increase traffic. They’re a reason, in other words, that locals pay so much in rent, have so few places to shop, and spend so much time in traffic.

But as a July hearing on the subject approached, Alpert knew that making reasoned online arguments wouldn’t be enough. “What I was telling people was, we really need to get people to go, there’s going to be a lot of antis there, they’re really organized, they’ve got all these groups,” Alpert remembers. “And maybe our best hope is just to get enough people there so that the Zoning Commission sees that there are two sides to it, and then maybe they’ll be OK approving it.”

Sure enough, 24 advocates showed up to testify in favor of the zoning change, speaking far into the night. Only a handful came to oppose it. And the measure—a sharp blow to the District’s auto-friendly status quo—passed.

Since then, the triumphs have piled up. In December 2008, Greater Greater Washington—and the gang of policy nerds Alpert has enlisted to help him run it—demanded that the Washington Metropolitan Area Transit Authority partner with Google to create a better mapping application for Metrobus and Metrorail riders. The agency is finally doing just that. In early 2009, Alpert championed efforts to tax plastic bags in order to clean up the Anacostia River. The measure is now law. This May, in a now-famous incident, Alpert spotted D.C. Council Chairman Vincent Gray’s 11th-hour attempt to axe funding for the H Street NE-Benning Road streetcar, envisioned to be part of a future city-wide light-rail system. The blogosphere exploded and irate calls soon crashed Gray’s switchboard. Within hours of GGW’s action alert, the trolley budget was restored.

GGW now has a couple dozen contributors, and gets some 60,000 unique visitors a month. But that growth has only amplified the voice of its founder, who writes with a smartest-guy-in-the-room entitlement that’s impossible to ignore. An editorial board of one, Alpert this year has interviewed the major mayoral and D.C. Council candidates; his endorsements will serve as the final word for many in the voting bloc of smart-growth enthusiasts he’s helped educate and assemble. Meanwhile, candidates have started campaigning on smart-growth policies, hoping to tap the demonstrated size and influence of Alpert’s audience.

In just a few short years, Alpert has made himself arguably the District’s most important advocate on issues of planning and development—a guy who, without holding public office, occupying a university chair, or even having a day job, is going to help shape what Washington looks like decades from now. “His way is to push and push and push on people, and advocates very assertively for smart growth and new urbanism and all of these things that are important to make D.C. great,” says District Department of Transportation Director Gabe Klein. Before they roll out any new initiative, Klein says, his team wonders “what is David Alpert going to want to know, what is Kojo Nnamdi going to want to know, what is Dr. Gridlock going to want to know?” That’s pretty good company for a 32-year old Massachusetts native who was living in Brooklyn during Washington’s last mayoral election.

Alpert’s response to the streetcar reversal, castigating the mainstream media for not recognizing an instantaneous citizen response triggered by social media, had all the webby triumphalism of a Markos Moulitsas screed in 2004. Alpert is steeped in the netroots revolution and its determination to upset established patterns of how journalists relate to authority. But GGW, carefully focused to achieve the most provincial and yet concrete possible gains, is no chaotic and sprawling DailyKos. Alpert’s creation, rather, is the netroots all grown up.

Alpert—a small man with an impish grin who goes most places in shorts and sandals—works out of the cheerily blue-painted Church Street NW rowhouse he bought for $1.3 million in 2008. The bookshelves are lined with science fiction, old math textbooks, and seminal works on urban planning. His home office has one map of D.C.’s Comprehensive Plan and another of the District’s World War II-era downtown. His laptop is plastered with stickers of his own creation: The iconic Obama logo, one with a stylized train coming out of the center, and another with two “O”s as the wheels of a bicycle.

(Photograph by Matt Dunn)

For all his big-city urbanism, Alpert started life in the most suburban of places: Acton, Mass., the son of a lawyer and a homemaker who did interior design on the side. Early on, his father brought home an Apple IIe, which little David used to learn programming instead of playing games. Though interested in government, Alpert studied computer science at Harvard, figuring he’d rather write code than write history papers.

Graduating at the height of the tech bubble in 2000, he joined a startup and moved to Silicon Valley. The enterprise tanked, but Alpert landed on his feet as a project manager at Google. (The little intra-site bullets that come up under each homepage when you Google something? Alpert made those.)

Within a few years, though, the monoculture of Google’s suburban Mountain View, Calif., campus became stifling. Alpert convinced the company to let him move to its New York City office. At a 2004 State of the Union watch party in Manhattan, he hit on his first foray into Web organizing: The early form of Drinking Liberally, a group of lefty friends who got together to imbibe and commiserate at the height of the Bush administration. (Alpert, who doesn’t drink much, is proof that you don’t have to be an alcoholic to join). In his spare time, Alpert built the website for what would become Living Liberally, a social-political organization with chapters all over the country.

“He immediately got it,” says founder Justin Krebs. “His role was thinking about how to build something that could scale nationally.”

In 2007, Alpert’s future wife Stefanie got a job in the D.C. office of law firm Wilmer Hale. The couple decided to move, and Alpert left Google behind. “When I started at Google, if you had an idea, you could run it by Larry or Sergey at lunch,” Alpert says, referring to company founders Larry Page and Sergey Brin. “By the time I left, it was 15,000 people, and there was a lot more process…Getting a product done was more about navigating this process and navigating the bureaucracy or the competing interests, as opposed to spending your time coming up with ideas.”

(Photograph by Matt Dunn)

Of course, it wasn’t quite as scary for Alpert to quit his job as it might be for most people: Though he declined to elaborate on his personal finances, let’s just say that six years at Google left Alpert sufficiently well off that he wouldn’t need to scour the want-ads for a long, long time.

Alpert’s first idea for using his stock-option-subsidized free time was a failure. Building on the Google ethos, he started a blog called IPac with the goal of advancing Internet freedom; one campaign involved sending iPods to recalcitrant senators so they could appreciate the value of downloadable music. With insufficient enthusiasm, IPac fizzled, and Alpert needed a new project.

It arrived in the form of a void: D.C. had development blogs and neighborhood blogs, but nothing like a Streetsblog, the influential nonprofit-funded website that focuses on progressive urban planning and design. Urban geekery had become a side interest of Alpert’s in New York, where he absorbed knowledge about the city’s subway system and worked on efforts to rethink Park Slope’s pedestrian-unfriendly Grand Army Plaza. He read books by Jane Jacobs, the pioneering grassroots activist who fought 1960s urban renewal and extolled walkable, 19th-century neighborhoods. So in February 2008, Alpert designed a website, posting several items a day on things like traffic waves and environmental impact statements.

GGW grew steadily from there. National bloggers who Alpert knew from his netroots life, like Matthew Yglesias and Duncan Black—a.k.a. Atrios, who writes at Eschaton—drove traffic his way. A popular early feature was a series of fantasy Metro maps, depicting the transit system with extended lines and different options. At one point, WMATA’s director of long-range planning asked if he could use one of them for a presentation; Alpert gladly obliged.

A few months in, Alpert began to expand the franchise. His first addition was Michael Perkins, an engineer who had started a blog called Infosnack, synthesizing Metro and other transit data. Then came Jaime Fearer, who was running a blog about Ward 5’s Woodridge neighborhood while going to urban planning school at the University of Maryland. Soon after, Matt Johnson, who’s now working for the Montgomery County planning department, started cross-posting from his blog Track Twenty Nine. Many of the contributors are professionals in the field, writing posts in their free time (nobody gets paid, and Alpert accepts neither advertising nor donations). Members of the club—who adhere loosely to different “beats”—banter throughout the day on an internal e-mail list refereed by Alpert, who encourages e-mailers to write posts about hot topics. Alpert edits every post for clarity and concision, writing headlines, managing copy flow, and catching factual mistakes.

The growing klatch of experts, cultivated and tended by Alpert, has become a one-stop-shop for D.C.-area smart-growth discussion. That’s why Streetsblog hasn’t needed to start an offshoot here as it has in Los Angeles and San Francisco, and why more traditional advocacy groups like the Coalition for Smarter Growth don’t have local blogs either.

“David has given us the best in the nation in terms of blogging communication,” says Stewart Schwartz, president of the 13-year-old coalition. “It taps into some very smart people in the Washington, D.C., region. I may not be using the term correctly, but it is a form of crowdsourcing.”

For transit enthusiasts, GGW supplies a degree of wonkery long missing from the public sphere. Metro Board of Directors member Chris Zimmerman has published editorials there; he sees it as a way to get in front of an audience that believes in Metro’s fundamental mission, at a time when newspapers rarely get into how the system works.

“It used to be that you could learn a lot about Metro by reading the Post. That’s not what the newspaper is doing anymore,” Zimmerman says. “…The Examiner isn’t interested in Metro getting better, it’s interested in having something to kick. It’s an ideological mission for them. And I think the Post is just looking for a headline that will allow them to sell past the Examiner.”

But while Alpert digs up information as well as any journalist, GGW is a fundamentally activist enterprise—and you won’t necessarily get both sides. Cavan Wilk, a financial economist who is also a Montgomery County transit activist, has been posting interviews of local politicos who are friendly to his agenda. “I don’t explicitly say it, but I assume my readership thinks that if I interview someone, then I like them,” Wilk says. “And I do not interview candidates that I don’t like, because I would ask them very uncomfortable questions.”

Would that be a bad thing?

“No, but they wouldn’t want to sit through that kind of interview, because they’re going to get that from journalists anyway,” Wilk says. “And I can do things that journalists can’t, because I don’t have to maintain an objective position.”

One evening in mid-August, while Alpert was vacationing on Martha’s Vineyard, the GGW crew—mostly male, totally white—gathered in a Hyattsville bar for one of its more-or-less monthly happy hours. Alpert had hosted dinners for contributors, but the community broadened after Johnson, who had few local friends when he arrived from Atlanta in 2007, began organizing meetups around the metro area (he chose Hyattsville because there hadn’t yet been any in Prince George’s County).

Upon walking in, I met Malcolm, a reedy young man wearing a tie featuring heads of the presidents, who works for the National Association of Railroad Passengers. A frequent commenter, who introduced himself as “Froggie,” circulated fantasy maps depicting vast new subway extensions. “Sandbox John,” who maintains a website with incremental photos of the progress of the Dulles Metro extension, brought several copies of an early Metro plan.

“Ooh, is that the 1998 map?” asked Johnson, ogling it like a rare baseball card. “I have the 1999.” The chatter moved so quickly from there that I could only catch snippets. The GGWers inveighed against poorly designed Metro stations (New York Avenue-Florida Avenue-Gallaudet University bore the brunt of the abuse), debated the merits of pocket tracks (for the uninitiated, that’s a secondary stretch of rail similar to a breakdown lane on a highway), and swapped stories of historic Metro crashes (“And well, you know how the 1000 series performs in accidents…”). At one point, Johnson leaned over apologetically. “You’re witnessing an extreme geek moment,” he said.

The geeks, though, are trendsetters. Alpert’s favorite D.C. councilmember, Ward 6 Democrat Tommy Wells—who stopped by a recent happy hour—has been on a precipitous smart growth learning curve, reading magazines like Dwell, going to conferences on rail transit, and keeping up with urbanism blogs. Running for a second term this year, Wells is campaigning on a smart growth platform; his yard signs feature the slogan “building a livable, walkable city.”

“When I first ran for council, I thought a lot about why do we like where we live, and why are people moving back to the city,” says Wells, who has lived in D.C. since 1985. “I didn’t come into this job being very knowledgeable about it. But I certainly have gotten a whole lot more knowledgeable about it.”

For all his interest in creating a community around smart growth issues, Alpert can name no specific hobbies of his own. He doesn’t need them: GGW is both vocation and avocation, keeping him wired socially and politically. At this year’s Netroots Nation—Alpert was an early participant when they were originally organized as YearlyKos—he was invited to moderate a panel on transportation policy.

“It’s hard to get to know him because he’s so busy,” says Fearer, who now lives in Trinidad. “I don’t even know all the things he does. ‘Oh, he’s going to be on a panel with [Transportation Secretary] Ray LaHood, O.K.’ I get the impression that he’s too busy to stop and tell us until he’s on his way.”

Alpert stands apart from many of his contributors in that he isn’t just a programmer or a map maker or a policy analyst. Most essentially, he’s an operator, seeing political dimensions that some would prefer to ignore. In a city where local government is often an afterthought—and where technologically sophisticated local policy advocates are few and far between—Alpert’s willingness to work the levers of power explain why he’s managed to become such a force in such a short time.

One recent Wednesday evening, Alpert sat in WMATA’s downtown conference room at a meeting of the Riders Advisory Council. After the group finished discussing proposed changes to the Blue Line—with a GGW-logoed map projected from Alpert’s laptop—they turned to what Alpert saw as a looming threat: What environmental and smart-growth groups suspect is a plan by the Metropolitan Washington Council of Governments and the Greater Washington Board of Trade to boot elected officials from the Metro board and replace them with appointees of area government executives. The Board of Trade says the status quo is not up to managing a complex transit system. Alpert, on the other hand, thinks Metro would benefit from more public input, not less; he’s suggested WMATA board members be elected by riders.

Alpert had drafted a letter to the two bodies asking for the same information they had been given so that the RAC might form its own recommendations. But a few members of the RAC didn’t get the point of trying to outmaneuver the business group’s task force.

“I dunno, it sounds to me like we’re saying, anything we come up with is going to be superior to what you’re doing,” one member objected.

“I’m opposed to sending the letter, because I think the tone is nasty,” said another.

“What do we care?” asked a third. “I understand that we’re not involved, but we’re involved in our own body.”

Alpert listened, growing more exasperated. Toning down the language, he said, would mean sending nothing but “the most inoffensive and innocuous letters.”

“That’s a recipe for being an ineffective public body,” he snapped. “And I’m not interested in being an ineffective public body.”

Ultimately, Alpert compromised, taking out some forceful paragraphs to gain the majority’s approval. Later, he described a conflict in the RAC over whether it should simply serve as a focus group for WMATA brass, or if it should be seen as a serious advocate for riders (of course, Alpert’s the only one with a megaphone).

That’s just one example of how Alpert negotiates between simply participating in the discussion and rocking the boat, simultaneously playing the insider and the outsider.

Richard Layman, an urban planner who has been blogging about D.C. urban policy issues since 2005, thinks Alpert pulls his punches to stay in the game. “David wants to be more of a player, so he won’t take harder core positions because that puts elected and appointed people off—they see critical analysis as personally-directed ‘criticism,’” Layman wrote in an e-mail. For example, he says, Alpert was too forgiving of Metro after the National Transportation Safety Board issued its scathing report on last summer’s deadly Red Line crash.

“He won’t take on whacked ideas from [D.C. Ward 1 Councilmember and Metro board member] Jim Graham (or I should say incomplete or incompletely developed ideas) because he wants to maintain access.” (Among the “whacked ideas” Layman criticizes are laws to require people to shovel their sidewalks and securing public money for a massive parking garage at Columbia Heights’ DCUSA shopping complex).

Alpert disputes that charge, citing the number of times he’s criticized Graham—over opposing rate hikes to prevent cuts in service, for example—as well as Gabe Klein, whom he castigated for narrowing bike lanes on Pennsylvania Avenue NW after they had been put in. But Graham also put him on the Riders Advisory Council, and Alpert will therefore probably not make an endorsement in the Ward 1 race. “Having a relationship with a politician is powerful,” Alpert says.

Alpert and the GGW gang are hardly the first people to be drawn into D.C. politics by debates over the shape of the city. Many the city’s political leaders in the early days of Home Rule cut their teeth during the epic fights against 1960s-era plans to build highways through various parts of the District. Perhaps the most apt precedent for Alpert’s activism is the late Cleveland Park lawyer Peter Craig, who led the anti-highway forces.

“The experts proposed a pretty bad idea, and were corrected by the people,” says Zachary Schrag, an assistant professor at George Mason University who wrote the Metro nerd bible, The Great Society Subway. “His tools were the typewriter and the mimeograph, but had blogs been around in 1959, I imagine his would have looked something like Greater Greater Washington.”

Instrumental in that earlier effort was the Committee of 100 on the Federal City, a now-87-year-old organization dedicated to the preservation of the original L’Enfant plan for the city. Thanks to their relentless advocacy, D.C. remains a walking-scale city, retaining many of the elements of a healthy urban environment that Alpert & Co. promote today.

But revolutions always eat their young. And now, a generation later—a generation during which the powers that be finally realized that urban renewal and downtown freeways were a lousy idea—there’s little love for GGW among some of their forebears.

Take this column from the Committee of 100’s chairman, which appeared in the organization’s newsletter in 2008. It didn’t mention Alpert or his blog, but the identity of the “insidious” force it slams was pretty clear nonetheless: “The Committee of 100, a scarred veteran of freeway battles and early champion of D.C.’s Living Downtown, is being tarred as a gaggle of aging couch potatoes bitterly clinging to cars and big houses,” the message reads. “The mischaracterization is coming from so-called ‘smart-growth’ advocates who want to recreate Washington, DC as a high-density destination for the healthy, wealthy and young…. Smart growth, as experienced by many District residents, has come to mean demands for multi-family mixed-use development on every available scrap of land without regard to need, scale, balance, or the opinions of impacted District residents. This is coupled with hostility toward all automobile use, whether or not any other form of transportation is available. To live in this ‘smart’ vision of the District, you should be willing to forego elbow room and to accept that a neighbor who enlarges his house may be literally an arms length away.”

In other words, says Committee of 100 Chairman George Clark, Alpert’s crew wants to turn D.C. into a Manhattan-esque metropolis. “I like the Upper West Side, but I don’t want to live there,” Clark says. “If I wanted to live there, I would move there. We’re Washington. We’re a capital city, we’re a world city, and we’re different.”

Furthermore, Meg Maguire, the Committee of 100’s point person on streetcars, says the “anti” caricature is inaccurate and unhelpful when discussing massive public projects. “I think with David, you’re either for something or you’re against it,” says Maguire. She says her beef with D.C.’s streetcar initiative had to do with poor planning and lack of funding, not an objection to change on principle. “I think he mischaracterizes our position when we raise complex issues, like how [the streetcar] will be paid for.” (Zartman, the preservationist Alpert recalls as his first “anti,” died earlier this year).

Alpert, in fact, says he does appreciate historic preservation—and doesn’t think developers should be given carte blanche to build as big as they want. He just thinks that today’s preservationists, who formed their alliances back when opposing things was the best way to defend the city’s livability and charm, have gone overboard.

“Now, you’re also starting to veer into preservation being about preserving the mistakes,” Alpert says. In between bites of a spinach salad at the Dupont Circle Sweetgreen, his feet up on a chair, he cites historian Richard Longstreth’s argument against demolishing the Third Church of Christ, Scientist at 16th and I streets NW as an example. Preservationists opposed bulldozing the unloved, Brutalist structure because it now represents a bygone era. “I thought he could probably say that about the dirt that’s along the edge here of Connecticut Avenue, that should be landmarked, we should never clean that up, because in such a such year there was dirt there, and that was when Eleanor Roosevelt walked by, you know, or something like that.”

Though they can land on different sides of development debates today, the preservationists who fought highway planners of the 1960s and the smart-growthers who battle parking lots of the 21st century share a common denominator: They’re easy to paint as rich dilettantes.

A glance at the overwhelmingly white happy hour crowd underscores the perception that Alpert’s group represents one part of the city prescribing solutions for another—which, no matter how logical their ideas, can create a public relations problem. Councilmember Wells, for example, is facing an energetic challenge from a black candidate who suggests to long-term residents of Ward 6 that things like bike lanes and streetcars are just ways to attract new residents, wholly irrelevant to the more pressing issues of crime and education.

Alpert is conscious of perception issues, and is careful to argue that more options for transit mean better access to employment for low-income residents. He’s also expanded the blog in recent months to include more content about poverty, and is thinking about branching out into education. But Schrag puts his finger on the difficulty Alpert faces in claiming the populist high ground, at least where cars are concerned.

“The tension there is that most Americans really like cars, and they don’t like cars as objects, they like cars because they get where you want fairly quickly,” Schrag says. “If you’re really going to be populist about it, it’s hard to be that stridently critical of the automobile.”

It’s all about choices. And for Alpert, dividing the world into two camps—like deciding whether Vincent Gray is a safe choice for smart growth advocates or not, the subject of a five-part GGW series—is just a way of clarifying those choices. After all, Alpert has made his own choices, like leaving the highways and strip malls of Mountain View for the sidewalks and local retail of Brooklyn. Every seemingly small choice made by local zoning boards and transit agencies and elected officials will help decide whether the District of the 21st century will look more like the former or the latter.

Running Greater Greater Washington gives Alpert a way to affect as many of those decisions as possible. He’s has contemplated serving in government someday, but that would probably involve working on one project for long periods of time. Shaping D.C. into his urbanist vision is a much more comprehensive thing.

“I think that there’s a debate going on, something of a battle, of how to conceive of development and growth in the city,” Alpert says. “And I want my view of that to prevail, because I think it’s right.”