It ain’t easy running against incumbents in D.C. politics. It’s especially hard when the incumbent is Marion Barry.

Consider the plight of Barry’s former spokeswoman, Natalie Williams (pictured above, when she was working for Barry), and the lengths she had to go on Tuesday to get some attention for her bid to unseat her old boss.

Around 11 a.m., Williams and a small group of supporters arrived at the empty waiting room of Barry’s Wilson Building office, accompanied only by LL and a cameraman from WUSA9. The pretext was to protest a proposed group home in Ward 8. Williams and other critics have said the ward is oversaturated with social services organizations. But the real reason for the sit-in, of course, was to get noticed.

At first, Williams wasn’t going to be disruptive, so she sat silently on the floor at the foot of the desk of Barry’s absent receptionist. That plan lasted only a brief moment until Williams announced that she did, in fact, have a message to convey.

“Whose ward?” she yelled. “Our ward,” her supporters replied on cue.

At the cameraman’s request, the group bundled together for a more telegenic pose.

“Ward 8,” Williams continued. “Elevate,” the group yelled.

While the chanting went on, LL wandered towards the back of the office to see what Barry’s staffers thought. They barely seemed to notice. One aide indicated that Barry, who was at a news conference for new affordable housing in Ward 8, was on the phone and wanted to speak to LL.

Barry lashed out at Williams, calling her objections to the proposed shelter in Anacostia “callous” and “un-Christian.” He said Williams needed to be protesting the unnamed businesses who won’t hire homeless women.

“She’s sitting in the wrong place,” Barry said. “I’m about the renaissance of Ward 8.”

Williams then took her protest outside Barry’s office into the halls of the Wilson Building, where security asked her to leave. Once a few protesters from the Occupy D.C. rally at the adjacent Freedom Plaza were attracted by the chants and came over, unwittingly joining the protest against a group home. One guy named Kyle, who wore a Guy Fawkes mask inspired by the movie V is for Vendetta, was handed a sign saying “4 More? Hell No!” as he posed with the Williams group in front of the TV camera.

Later, he and Williams commiserated over the real problem in the world: that the majority of people just didn’t know what was really going on. “Sheep,” Kyle called them.

Beating Barry will take more than political rallies that depend on Occupy D.C.’s overflow, for Williams or any of the other three candidates running against him. (Another candidate will probably be dumped from the ballot for submitting qualifying petitions with bad signatures, and another just dropped out.) While Barry’s four terms as mayor proved plenty, his legacy as a civil rights leader and vocal defender of the city’s poor—even if he hasn’t been their best actual defender—has probably earned him the Ward 8 seat for as long as he wants it.

“If you get online and Google Marion, you get where you come from and where you’re going in the struggle,” R. Joyce Scott, the head of the Ward 8 Democrats, said at the group’s meeting last Saturday.

Which means the current election may really be a contest for who is best positioning themselves for the post-Barry years.

Barry, according to a report in the Washington Post, has told people he plans on serving only two years before setting his son Christopher Barry up as his replacement. Barry says he planted that rumor as “bait.” Last fall’s guilty plea to drug charges might also have complicated the younger Barry’s plans. But the fact that people are talking about it only underlines the fact that the former-mayor-for-life won’t always be the Ward 8 councilmember.

Still, he’ll almost certainly be sitting in the same seat at the D.C. Council dais come next January. There haven’t been any public polls of Ward 8, but Barry certainly doesn’t sound crazy when he predicts he’ll get about 70 to 75 percent of the vote. In fact, he’s so sure he’s going to win that he’s repeatedly beckoned challengers into the race.

At Saturday’s Ward 8 Democrats meeting, Barry praised the courage of those who “dare to step forward” and run against him.

“The more, the better,” Barry said.

For him, that is. Beating Barry one-on-one would be tough. Doing it while splitting the ward’s relatively small anti-Barry vote seems downright impossible.

But ask the group currently challenging Barry, and they’ll each tell you the same thing: They see how they’ll win, but none of the other candidates has either a clue or a chance.

Besides Williams, Barry’s challengers include: Jacque Patterson, the former president of the Ward 8 Democrats, who got 4 percent of the vote when he ran against Barry in 2004; Sandra Seegars, a community activist who lost to Barry both in 2004 and 2008, when she got 9 percent; and Darrell Gaston, an energetic 25-year-old ANC commissioner whose campaign strategy includes telling public housing residents that Barry supported ending the District’s open-ended welfare system: “We let them know, ‘Hey, Barry wants to cut your benefits.’”

Seegars says you can find proof of the rest of the pack’s fecklessness in their inability to challenge the signatures their rivals submitted to get on the ballot. She says the other candidates talked about challenging petitions, but only she actually did it.

“They sat back to wait for the woman to do the work, and I did. I get things done,” says Seegars. “I wish I could have knocked off all of them.”

Gaston says his record as an ANC commissioner is one of working in the “trenches” to help Ward 8 residents find jobs or avoid evictions. Meanwhile, he says his opponents have spent their time helping business groups gain power or “doing beauty pageants,” references to Patterson’s involvement with the pro-business Federal City Council and Williams’ spokeswoman work for the Miss Black USA organization.

And Patterson says flat out that he’s the only serious candidate of the whole bunch.

Posturing aside, a look at fundraising shows that none of the candidates have done well in the area any challenger would need to beat an entrenched incumbent like Barry: raising money. Financial reports released this week show that with two months left before the election, none of Barry’s challengers have much cash.

Patterson managed only to raise $4,353 despite telling LL that he’d been in talks with some of Barry’s long-time donors. Williams’ haul so far isn’t much better at $4,758. Seegars has raised only $1,340. Gaston raised a respectable $22,000 during the last reporting period but says his fundraising has slowed down during the last couple of months. (Neither Gaston or Barry had their most current reports available online by LL’s deadline.)

That kind of weak financing suggests that the race for second is still wide open. But for now, it looks like only Barry can decide when that Barry-free future for Ward 8 comes to pass.

Photo by Darrow Montgomery

Got a tip for LL? Send suggestions to lips@washingtoncitypaper.com. Or call (202) 650-6951.

More from WCP