On the night of June 30, Ward 5 D.C. Council candidate Kathy Henderson got an unwelcome media boost for her campaign. Someone torched her 1991 Capri convertible near her Carver Terrace home. It didn’t take long for the television and newspaper reporters to start calling.

She says the fire was the work of neighborhood thugs who had threatened her in the past and damaged her car and other property. As an advisory neighborhood commission member, Henderson, 44, has pushed for more cops on her street. She’s never backed down from the local tough guys.

Being victimized may be what it takes for a candidate like Henderson to get noticed in the city’s most crowded political contest. She is running for an office being sought by 14 others, including a few ANC members who can roll out similar crime-fighting tales. According to the D.C. Board of Elections and Ethics, the Ward 5 race has more candidates than any single regularly scheduled council contest to date. (A 1995 special election in Ward 8 drew 21 entrants.)

The crowded field should be expected in a town with a political setup that stifles civic ambition. This city, after all, isn’t part of a state or county and has no meaningful representation in Congress. So anybody with political aspirations inevitably gravitates toward the council races, where the reward is what can be a pretty easy job with long summer vacations and a salary of $92,520. And this year, two-term incumbent Vincent Orange is abandoning his Ward 5 seat for a quixotic shot at the mayor’s office.

The dynamics of the race are classic D.C. Though the city has undergone huge social changes in the past decade, the old guard remains firmly entrenched in Ward 5, which occupies much of the District’s Northeast quadrant.

Just look at the putative front-runners. Harry “Tommy” Thomas Jr., 45, lists being the son and namesake of the legendary old-school Ward 5 councilmember as a chief accomplishment. The other candidate at the front of the pack, Frank Wilds, 62, is a Ward 5 Democratic Committee activist and retired businessman. Wilds is a self-proclaimed political organizer and a magnet for big-business cash. Neither man inspires a lot of passion beyond an inner circle of hangers-on, job-seekers, and well-connected lobbyists looking to solidify their grip on the D.C. Council.

Voters eyeing the balance of the field find a gaggle of former city workers, advisory neighborhood commissioners, and activists. Their mostly low-budget campaigns all hinge on a personal touch and a hope that voters are fed up with the same old guys.

With gentrification sweeping eastward into Ward 5 neighborhoods like Brookland, Eckington, and beyond, this could be the last election for candidates to showcase the traditional Ward 5 themes of bad schools, crime, and uneven delivery of government services. To celebrate the last gasp of machine politics, the Washington City Paper offers this look at those who are pursuing the Ward 5 crown.

***

The Candidates

***

Philip Blair (Statehood Green): Retired last-minute entrant is the listening candidate. Thinks Democrats ignore voters’ real concerns.

Joe Harris: Outsider. Nonprofit administrator is attempting to follow same path as Ward 7 councilmember and nonprofit guru Vincent Gray.

Kathy Henderson: Street-level activist. D.C. government worker and ANC member plays up crime-fighting experience.

Regina James: ANC member. Slots opponent and Ward 5 native lacks organization but has plenty of street cred.

Ron Magnus: Former D.C. Office of Attorney General lawyer. His mission: save the city’s youth.

Bruce Marshall: Government worker and staffer to first Ward 5 councilmember offers novel platform: competent management.

Miriam Moore (Independent): Ward 5 newcomer. Internet-based campaign highlights her New York City gentrification experience.

Audrey Ray: Ivy City rabble rouser. Low-budget effort focuses on working through challenges rather than talking about them.

Steve Rynecki: Former North Capital Main Street chief. Calls for new style of leadership in the ward.

Deborah Smith: Another ANC member hoping to move up. She’s convinced progress on her Edgewood block can be extended to the entire ward.

Carolyn Steptoe (Statehood Green): Anti-gentrification crusader who recently registered as Green to get in the race.

Harry Thomas Jr.: Legacy candidate claims seat as family throne.

Frank Wilds: Businessman and Democratic Party activist. Organizing skills, community knowledge, and business ties make him the man to beat.

Vera Winfield: City’s barber and cosmetology board chair emphasizes both Ward 5 roots and a willingness to welcome new residents.

Raenelle Zapata: Former DCRA official stresses her front-row view of city’s role in gentrification battles.

***

The Bandwagon Still Rules

***

The Stance

***

The Supporters

***

The key to victory for the lesser-known Ward 5 hopefuls will be finding a way to stand out from the crowd. So far, that’s been a tough task for a group predictably focused on hitting the hot-button issues everyone thinks will resonate with the voters. If ward residents are expecting a big field to generate a pile of new ideas or novel political themes, they should think again.

***

The Stance: We must improve the D.C. Public Schools!

***

The Supporters: No need to pore over the positions of all the candidates on the No. 1 issue for D.C. voters. Everyone is a schools reformer. The only separation on the issue of our time comes in the form of bragging rights: In a rare display of homegrown pride, several candidates claim to have been a product of the city’s public schools.

***

The Stance: We must enhance police presence in our neighborhoods, where we and our children live!

***

The Supporters: These days, the get-tough-on-crime platform is less a selling point than a required ticket for any D.C. political contestant. From Thomas’ “crime blog” to efforts by James and Henderson to personally patrol their neighborhood streets, you can’t find a Ward 5 hopeful who isn’t a superhero.

***

The Stance: I will represent all the people of Ward 5, not just the rich and powerful!

***

The Supporters: Putting middle-class and poor constituents above the usual influence peddlers at the John A. Wilson Building is an easy pledge to make. But lots of candidates in the race have deep D.C.-government roots or have taken cash from entrenched fat cats. Only a chosen few can boast of having no ties to the stale, old political establishment that is making a last-gasp effort to keep a grip on the fast-changing ward.

***

The Stance: I will fight for the self-esteem of young people!

***

The Supporters: Everyone talks about being the candidate for youth, but only two candidates have a specific platform to address the core problem of childhood disillusionment, pledging a self-esteem boost for the city’s kids.

***

Atlas Of Ward 5 Political Hot Spots

***

No Ward 5 voter can make it through a candidate forum, or even a sidewalk pitch, without hearing about these local political landmarks.

Dream (now called Love)

This popular nightclub has become synonymous with Vincent Orange’s annual birthday bash. Throw in complaints from neighbors about noise and trash plus the charismatic club owner, Marc Barnes, and you have a genuine political roost.

Colonel Brooks’ Tavern

The tavern is no longer just the multiethnic intergenerational hangout that is the pride of Brookland. It’s a place where highflying politicos come to prove that they can sit with regular people and eat fries.

Home Depot

The arrival of the hardware megastore, along with a Giant supermarket, raised hopes that the large swaths of industrial land and vacant retail complexes in the ward would soon fill up with major national chains. Home Depot is now viewed by some as a bright-orange monument to the dreams of the ward’s current councilmember and mayoral aspirant.

McKinley Technology High School

The reopening of McKinley is seen as the best gift the ward received from the city’s economic renaissance. The once-shuttered school is now a beautiful, white-pillared building boasting one of the grandest views in the city. Several 2006 council hopefuls brag about their time at McKinley as a way of boosting their Ward 5 cred.

Trash Transfer Corridor

The stench of garbage emanating from the trash-holding zone in Ward 5 fuels a lingering image of the Northeast quadrant as a neglected dumping ground for the city’s problems. Previous efforts to shut down the transfer station have been successfully beaten back by legal threats from former Councilmember John Ray, who contributed $500 to the Wilds campaign.

***

The Bungalowdown

***

Ward 5 enjoys a reputation as home to some of the most down-to-earth neighborhoods in the city. The middle-class-heavy ward has pockets of poverty and no Gold Coast. In short, Ward 5 is real.

We rated several council candidates on their realness, with Ward 5’s ever-present bungalow as the unit of measurement. A rating of one bungalow means the candidate isn’t a natural on the front-porch swing. A rating of 10 bungalows means the candidate thrives in all bungalow situations.

Bruce Marshall

Lifelong Ward 5 resident. Married local gal. McKinley Tech High School football letterman. Worked for city and feds.

Audrey Ray

Arrived in Ivy City at 12. Left for a few years, returned to care for mom. McKinley Tech grad. Hanging tough in Ivy City.

Kathy Henderson

Longtime city worker. Refuses to surrender Carver Terrace to thugs.

Harry “Tommy” Thomas Jr.

Son of Ward 5 councilmember. Youth-baseball booster. D.C. public-school product.

Regina James

Reared in the ward. McKinley Tech grad. Former union-shop steward.

Deborah Smith

McKinley alum. Led refurbishing effort of alma mater.

Frank Wilds

Delivered Schlitz beer to local bodegas. Lives local politics.

***

Money, Money, Money

In a crowded political contest, nothing separates the big guys from the also-rans like cash. Printing T-shirts, staging events, and renting out a storefront project a political permanence not conferred by the random street sign.

In the bloated race for the Ward 5 council seat, two front-running candidates—Thomas and Wilds—will report more than $50,000 in contributions. On the other end of the spectrum, a couple of candidates have filed papers indicating that they don’t plan to raise more than $500.

In between, there’s a lot of room for big-money, medium-money, and small-money donors to own a candidate or two. Our pie charts reveal a mad scramble for any kind of money in Ward 5’s corridors of power. And a bit of sleight of hand as well.

For instance: Thomas’ use of in-kind contributions has enabled him to “win” his cash showdown with Wilds by a margin of $49,545 to $46,842. At least he’s the fundraising champ on paper. Thomas understands the value of appearances. In fact, he was willing to stretch the definition of contribution to keep his front-runner status.

Harry “Tommy” Thomas Jr.

A few of Thomas’ in-kind listings seem legit. Who could argue with a $500 in-kind party thrown by the Solar Eclipse Restaurant and Club? But when Thomas’ brother-in-law Spillman Truhart was asked about his $500 in-kind gift, he didn’t have any idea how he’d ended up on the report. “You need to talk to my wife,” he says.

Thomas listed 27 in-kind contributions, including $10,000 from himself. (For more on Thomas’ reporting shenanigans go to washingtoncitypaper.com/citydesk.)

Vera Winfield

Winfield is pretty much financing her entire run for office. But if Winfield wins she’ll have to answer to charges of undue corporate influence in her campaign. Of the $1,850 she’s collected from outside sources, 46 percent comes from employees of three local companies—BET, the general contracting firm Consys Inc., and Comcast. No word on whether other cable and contracting giants are queuing up to hop aboard the Winfield bandwagon.

Regina James

A James victory will bring a little-known union to the front and center of the council’s political dialogue. Almost a third of her $1,645 total comes from a single $500 contribution from Reinforcing Iron Workers Local Union 201. It is still unclear if the hardhat-wearing financial backers plan to join James during her signature midnight-to-4 a.m. crime-fighting walks.

***

Bringing Georgetown to Brookland

***

The construction of a Home Depot and a Giant on a huge expanse of asphalt just off Rhode Island Avenue NE has gotten Ward 5 thinking big. Although all candidates have a stock line embracing mom-and-pop stores, the consensus is that the ward has “arrived.” In economic-development terms, that means it’s time to bring in the chains. For instance, candidate Wilds has vowed to continue Orange’s annual pilgrimage to the big retailers’ conference in Las Vegas to woo more big-box powerhouses to his back yard, but he’s added a preference for corner-sized 12th Street–scale outfits. Here are a few of the candidates’ visionary picks:

Joe Harris

“Something like a Gap would work,” says Harris. “We can create a Georgetown in Ward 5.”

Frank Wilds

“I’d like to see a Starbucks or a Seattle’s Best,” he says. “That’s the type of growth we could use.”

Vera Winfield

“My personal choices may not be the same as many other residents,” she says. “For myself, I would love to have a Bed Bath & Beyond.”

Deborah Smith

“We need a decent sit-down restaurant,” says Smith. “Something like Panera Bread.”

Raenelle Zapata

“Our neighborhoods have changed tremendously,” she says. “We are looking for more stores. We would like to have something like a Target or Marshalls. You know, the stores you find in the surrounding suburban areas, to keep our tax dollars here.”

Steve Rynecki

“Firehook Bakery would be about right,” he says.

***