We know D.C. Get our free newsletter to stay in the know.

Standing on a tiny traffic island off Dupont Circle, Jim McLeod surveys the dismal scene around him. Though it’s a sunny summer day, he sees only gloom: Signs of his enemy are everywhere, bright red posters perched high on lampposts and poles, valentines to voters from a grateful incumbent: “Re-Elect Jack Evans.” McLeod sighs and finishes stapling his own campaign poster to a shoulder-high patch—the last bare spot on a plastered election totem pole.

McLeod’s black-and-white banner seems out of place amid the neon bloom of the surrounding posters. Baroque and busy with details, it’s less campaign promotion than civics lecture. Bold letters at the top announce, “WARD 2: Home of Monuments and 78,429 Residents,” a boast illustrated by a meticulously detailed map of the ward crammed with a photo collage of various buildings and statues. There’s also a snapshot crammed in of a briefcase-toting McLeod next to what his campaign has tried to pass off as a slogan: “Constant Vigilance is the price of liberty.’’ In small print at the bottom comes the belated punch line: “Vote JIM McLEOD for WARD 2 Council Member, a Lawyer Born in Foggy Bottom Who Will Work Full-Time to Represent Ward 2 Residents.” Not exactly a quick read for the motorists and pedestrians rushing by; it was only after printing up 1,000 of these Byzantine posters that McLeod fully realized his tactical error.

“My name is not big enough,” admits the quiet, slight McLeod in his deliberate manner. “We try to put them at eye level to get the most reaction from the public, but unfortunately, that also gets them torn down a lot, too. So we have a dilemma we hadn’t anticipated.” Despite his repeated use of “we,” McLeod has no real campaign staff, and no discernible supporters.

He may be new in politics, but he’s getting the hang of bright-siding any blunder. He points out that the posters are recyclable, environment-friendly (soy-based ink), and says the overarticulated message “gives the residents something to be proud of: ‘This is my ward, see how great it is,’” he says. “The fact that I’m going to put the residents first—that’s great—but if I don’t get name recognition, I’m not going to get elected.”

So far, recognition is just one of McLeod’s name problems: A newspaper report on the mostly ignored Ward 2 race misspelled his last name. Another dubbed him “John” McLeod. Even his ubiquitous name tag hasn’t helped much. At local forums, “McLeod” is mispronounced routinely; he now makes a point of telling people that his name sounds the same as Dennis Weaver’s horse-riding TV cop, McCloud, but is spelled like that of famous black educator, Mary McLeod Bethune.

All of which makes for a tough campaign for a first-time unknown who has no political experience, and who is challenging an incumbent, Jack Evans, whose last election was an unopposed romp to the D.C. Council in 1992. McLeod and Evans are vying in the Sept. 10 primary to be the Democratic candidate for the Ward 2 council seat. Ward 2 has 27,000 registered Democrats, compared with only a few thousand Republicans, so the winner of the primary is a shoo-in for the council.

The only part of D.C. that many tourists ever see, sprawling Ward 2 stretches from lower Georgetown to the riverfront on the Potomac and Anacostia rivers, embracing the downtown business district and the National Mall, as well as such neighborhoods as Shaw, Logan Circle, and Petworth. It’s not a city ward that makes headlines, but McLeod detects all sorts of trouble brewing, not so much in the streets as in the corridors of the council. His criticism of Evans goes beyond the usual carping of an unknown challenger against a comfortably ensconced incumbent. In fact, he considers Evans a dangerous enemy not just of Ward 2 but of democracy itself. “The person who’s the representative of this ward with so many monuments to liberty and freedom is just not upholding that tradition at all,” he says. “There is an anti-democratic and anti-liberty pattern to the legislation that Mr. Evans supports and introduces.”

While other candidates cavort around town chanting about crime and municipal mismanagement, McLeod has cobbled together one of the more obscure platforms in District history—all constitutional privilege and no potholes. In fact, what spurred him to challenge Evans is a legal issue that most people—even registered voters—aren’t aware of: In 1994, the council passed a law that did away with jury trials for misdemeanors; though McLeod sympathizes with this attempt to bypass the notorious bureaucracy of D.C.’s criminal justice system, he says the law has deprived too many District residents of their right to trial—and their right to sit on a jury: “If this was something that happened in China, we’d say, ‘How backwards those people are,’” says McLeod, a defense lawyer who often handles court-appointed cases. “If you want to put people away, fine, but don’t take away their right to a jury trial.”

McLeod is campaigning on the issue of liberty at a time when District residents are willingly surrendering it for greater safety. (Earlier this year the council passed a law allowing police to crack down on impromptu street gatherings if the cops suspect drug dealing. Community groups across town applauded the measure, while civil libertarians screamed bloody murder.) Even though he’s running for office, McLeod takes the scholarly approach, chiding potential voters as if they were errant schoolchildren. “They should have an appreciation of the significance of part of their right to participate in the criminal justice system,” he says. “In D.C., we don’t elect the judges, we don’t elect the prosecutors—the only participation we have is through the jury system….It’s the perfect model of how members of the community come together and deliberate about a common concern. The only other time we’re called upon to do something directly is to vote.”

McLeod’s other big campaign issue isn’t much sexier: He vehemently opposes Evans’ recent proposal to ban steel doors in the District, an attempt to prevent drug dealers from using the doors as barricades during police raids, and to stop the transfer of drugs and money through the doors’ mail slots. McLeod says the wording of the proposed resolution would effectively ban all steel doors, including the bars that many residents use to protect their homes from burglaries: “The target is a select group of people that are disobeying the law, allegedly,” says McLeod, claiming that the real victims of the ban would be homeowners who use steel doors for security. He says the misguided proposal is another example of how Evans is hopelessly out of touch with his own constituents, a charge the quirky McLeod might want to be careful slinging about.

It’s a Wednesday night in mid-August, and St. Thomas Parish is filling up with Dupont Circle residents eager to hear an airing of the issues in the Ward 2 race. The meeting room is a glad-handing politico’s dream: Voters and political junkies crowd the entryway and begin taking their seats. Everywhere you look, there’s a cluster of potential supporters waiting to be wooed.

A few minutes before the forum begins, McLeod blows by the multitude of chatterboxes in the entrance, makes a beeline for the front of the room, and takes a seat. McLeod appears to recognize no one in the crowd of die-hard Ward 2 activists.

In his opening statement to the crowd of 200, McLeod dives straight into his civics lecture/campaign platform, panning legislation “which is not traditionally democratic, and I find it to be of a nature that I consider to be anti-liberty, which I think is important to all Ward 2 residents, that we enjoy our liberty,” he says. Not content to leave well enough alone, McLeod then announces that he supports his own candidacy by default. “I could have voted for somebody else because I didn’t like what Mr. Evans did, but nobody else was running, so that’s why I’m here,” he says to a bewildered audience.

His opponent, Evans, may be a little full of himself, but he knows how to work the ward. In response to a question about his responsibilities, Evans shoots back: “On neighborhood issues…whether it means supporting the opposition to the cogenerator in Georgetown, or the rampant overbuilding in Dupont Circle…or the prostitution in Logan Circle…I have been there and have stood strongly with the residents to make sure that the quality of life of all of us has been protected.”

One week later, a forum sponsored by the Ward 2 Democrats showed why this race has the potential to be one of the most lopsided in the short history of D.C. elective politics. By the time the discussion began, the room—chock-full of voters wearing red Evans stickers—felt more like an Evans campaign rally than a candidates’ forum. Once the audience questions began, McLeod sat silent for nearly 20 minutes as voters directed their questions exclusively to Evans. Finally, a woman threw out a question for both of the candidates. McLeod exceeded the time limit in his response, at which point the timekeeper shouted, “Time, Mr. McGrath!” “It’s McLeod!” fired back the candidate. “OK, McLeod,” conceded the timekeeper. “But it’s still time.”

Lawyer, sailing enthusiast, and inveterate walker, McLeod seems unlikely to add political officeholder to his vitae and admits he possesses little of the smiling charm of Evans. The 42-year-old has lived in Ward 2 for a decade and says his only political experience was as class representative in law school. Invoking the struggle of early American patriots against British tyranny, he says he was driven to run for office to protest Evans’ voting record. Last spring, after he realized that no one was challenging Evans in the Democratic primary, he decided to take a shot. (His wife made him promise that they’d still take their Maine vacation the last week of August; McLeod says his absence just before the election will have little impact on his fledgling campaign, since most Democrats had the Chicago convention on their minds anyway.)

Dressed in his button-down shirt, casual slacks, and L.L. Bean loafers, McLeod has visited nearly every corner of Ward 2 on foot, introducing himself to residents and putting up campaign posters. Sometimes McLeod gets help on his rounds from a cabbie named Lennie. He and the candidate drive around the ward in Lennie’s taxi, loaded with a ladder and piles of posters. But for the most part McLeod walks his turf alone: “I’ve got great leg muscles,” he says. “I’ve walked around the ward many times now, and that’s the best way to cover it. Many people have told me they’ve never even seen Mr. Evans in their neighborhood.” McLeod says his defense work for indigent clients has made him familiar with the ward’s less affluent sections, such as the housing projects along M Street SW. He says that Evans is out of touch with the ward’s poor population: “People have told me that Mr. Evans just has the rich person in mind,” he says.

McLeod himself doesn’t mind extolling the fruits of the good life: He often spends his weekends enjoying a pleasure-seeker’s view of his beloved ward—sailing on the Potomac. For several years, he’s been a crew member of the good ship Poo, a 17-foot mob jack that has competed in national regattas: “Sailing is really something I love; it’s very exhilarating,” McLeod says. “When the wind is blowing, it’s the best exercise in the world, and you can look at the monuments. It’s a great thing.” Clutching the boat’s trapeze wire, hanging over the water, McLeod suddenly lifts off from ordinary existence to a higher plane between earth and sky: “You’re going superfast and all you hear is the wind,” he says. “You’re really together with Mother Nature.”

Back on land for an afternoon of canvassing, McLeod has put up a handful of posters and worked his way down to Foggy Bottom, where he was born and where he now lives. Busy as he’s been, talking issues and constitutional law, McLeod hasn’t found time during this excursion to glad-hand passers-by or solicit potential voters. He’s well aware that he’s not a flamboyant sort, and he’s even had trouble raising the necessary funds to distribute the 2,000 informational brochures he had printed up. “I’m not the best person asking for money, but I’m finding I’ll have to get better at doing that,” he says.

Until then, he’ll continue to go door to door with his own version of retail politics, in what is turning out to be a long, lonely foray into the world of D.C. elective office. McLeod has only his deeply held personal beliefs to peddle, and that’s a tough sell in the District.CP