Back in July, before most folks decided Mayor Adrian Fenty was a dead man walking, D.C. Council Chairman Vincent Gray pulled together a new media roundtable at Ben’s Chili Bowl, where a number of bloggers, ahem, grilled the candidate over policy issues. It was a fascinating choice of location.

Given that Fenty is struggling to connect with the black community that help put him in office four years ago, Gray’s team ostensibly zeroed in on the mayor’s weak spot by selecting Ben’s. With its five-napkin menu of chili-slathered half-smokes and cheese-covered fries, Ben’s is the kind of populist establishment that politicians have, for years, used as backdrop to align themselves with the District’s often marginalized African-American voters. Holding court at Ben’s has been historically tantamount to courting the black community.

Except in this case, Gray wasn’t trying to reach out to residents in the predominantly black wards. He was speaking to a group of mostly white bloggers who are already fully invested in D.C. politics.

The candidate’s choice of location was, in a sense, an acknowledgement that, while Ben’s hasn’t changed much in 50 years, the gentrifying neighborhoods around it have. Though still owned by the Ali family whose patriarch, the late Ben Ali, founded it in 1958, the Chili Bowl is an establishment embraced by many beyond the District’s black communities and the politicians who represent them. It’s a landmark with mass appeal.

“It’s more than an African-American restaurant,” says Peter Rosenstein, a long-time Democratic and community activist. “It’s a quintessential D.C. restaurant, and it is known around the country.”

But if Ben’s now belongs to the whole city, where should a pol go to court a narrower demographic? More specifically: Where do mayoral candidates go if they want a bite to eat and a chance to bite into the issues with black voters, who still make up (slim) majority of the electorate? The answer to the question is difficult, given that some wards still don’t have many sit-down restaurants, despite the addition of Ray’s the Steaks at East River in Ward 7 and the IHOP in Ward 8.

Some of the people I posed the question to suggested chains like Red Lobster and Ruby Tuesday’s (despite the fact that neither has locations in the predominantly black wards) or the relatively new Alabama Avenue SE IHOP, which is owned by a Ward 8 family. But the one place that repeatedly passed by people’s lips was Big Chair Coffee n’ Grill on Martin Luther King, Jr. Avenue SE in Anacostia, which an Ethiopian family opened earlier this year to an avalanche of publicity.

“The local politicos from Ward 8 and Ward 7,” one political consultant told me on background, “they all meet at Big Chair.”

Big Chair seems to be the safe choice for politicians looking to connect with voters across the Anacostia—certainly safer, it would appear, than that other high-profile addition to the area, Ray’s the Steaks at East River. When I mentioned Michael Landrum’s steakhouse as a possible rallying point for Anacostia residents, particularly given the restaurateur’s savvy adaptation of his concept to the neighborhood, one veteran restaurateur quickly dubbed it a “white man’s paradise. I don’t think that’s going to be embraced.” (Philip Pannell, executive director of the Anacostia Coordinating Council, strongly disagrees, saying that Ray’s is very popular among residents and sees no controversy with it.)

Regardless, Big Chair appears to have none of the gentrifying subtext that bothers some people about Ray’s the Steaks at East River. Big Chair was founded by Ayehubizu Yimenu and her family; Yimenu worked as a nurse for years at Birney Elementary School, further up the road on MLK Avenue, and has all the neighborhood credibility that no outsider could ever hope to gain, at least not instantly. Even Landrum thinks Big Chair is the perfect place for politicos.

“Big Chair is great as a backdrop for some political events,” he says. The place “does symbolize some great strides forward on Martin Luther King [Avenue].”

Perhaps the bigger point here is one that a local consultant made to me: The days of Marion Barry sweeping into office largely on a black vote are over. A mayoral candidate must get to know a broader landscape in the District, and that likely means getting to know where those many different constituents eat.

“In today’s world,” notes Rosenstein, “if you’re a politician, you want to be seen in as many places as possible.”

Those places vary, of course, depending on what demographic a candidate is trying to reach. After all, not every eatery can be the Java House on Q Street NW, where the hip little operation draws all sorts of residents from the ever-changing Dupont Circle neighborhood: writers, politicians, policy wonks, artists, gays, straights, families. It’d be the ideal place for any politician to engage with a broad constituency, one consultant noted.

But say a candidate wanted to target a narrower audience, such as the gay community? Pannell singles out Annie’s Paramount Steak House on 17th Street NW as a mecca for the District’s gay crowd, despite a recent pan by The Washington Post’s Tom Sietsema, who called it a “last resort for an omelet in the wee hours.” One consultant called Annie’s “the only gay restaurant in the city,” by which he meant that it’s the only one with an all-gay clientele, as opposed to some other stops, like Logan Tavern on P Street NW or the Duplex Diner on 18th Street NW, which can cater to a mixed crowd.

The politician hoping to appeal to D.C.’s affluent young families should pay a visit to Cactus Cantina on Wisconsin Avenue NW, where the kids’ grilled cheese sandwiches come in quesadilla form and the chicken nuggets are called pepitas de pollo. Better yet for harried parents and their fussy offspring, Cactus Cantina won’t make you wait like next-door neighbor, 2Amys, an equally family-oriented restaurant. Nor will you shell out the kind of cash at Cactus Cantina that you would at Peter Pastan’s place.

The downtown steakhouse, both restaurateurs and consultants point out, has historically been the spot to woo the District’s business community. But Ashok Bajaj, the politically savvy owner of several notable restaurants including Rasika and the Oval Room, noted that the economy has changed the way politicians think about connecting with local business owners. Or at least it should. Bajaj, for instance, owns both Ardeo and Bardeo in Cleveland Park, a neighborhood that has been shedding businesses at an alarming rate. He has been encouraging Fenty to visit one of the restaurants in Cleveland Park—maybe Dino or maybe his place—and talk about the mayor’s plan to revitalize struggling areas. That’s the sort of symbolism that will go a long way with local entrepreneurs, Bajaj suggests.

So did Fenty ever take up Bajaj’s idea? “No,” he says, “I don’t think so.”

The economy and gentrification may have altered politicians’ dining habits, but one has apparently remained deeply ingrained: If politicos want to cater to the District’s moneyed crowd, they still hang out at Café Milano, the Georgetown institution known for hosting the kinds of people who still drive black SUVs. The attraction here is simple—not only is the clientele still rich and powerful, but the owners know how to get a politician’s name into the gossip columns, which is half the reason to step foot into a place like Café Milano.

Of course, one local restaurateur thinks catering to the District’s rich is just a waste of time. They work all the time, he says. A K Street lawyer stays at the office “until 10 o’clock at night and bangs his secretary while the wife takes the kids to Cactus Cantina for dinner.” My source is quite tickled with himself as he concocts what he believes is a wholly realistic worldview of the wealthy.

We hang up the phone. He calls back three minutes later. He wants to clarify his previous position on the rich.

“No, the lawyer bangs his summer associate,” the source says. “They don’t have secretaries anymore.”

Eatery tips? Food pursuits? Send suggestions to hungry@washingtoncitypaper.com. Or call (202) 332-2100, x 221.