Jimmy Calomiris launched his campaign for a D.C. Council at-large seat in June with a platform that was vaguely Donald Trump-esque. A blocky businessman, Calomiris combined promises to cut through city hall red tape with a cheerful lack of knowledge about the job he was running for.

During one interview with LL, Calomiris revealed that he didn’t even know how many years a Council term lasts. Josh Brown—Calomiris’ youthful political consultant who has already served in prominent positions on several other local campaigns—cut in. With fellow political consultant John Rodriguez sitting next to him, Brown set to coaching the candidate right in front of LL. 

“You’re going to shake things up,” Brown told his client.

The District government never got the chance to be shaken. After LL reported about Calomiris’ previous conviction for attacking his girlfriend, as well as multiple positive drug tests for cocaine, the candidate dropped out of the race in July. 

The exit of Calomiris—and the personal wealth he had intended to invest in the campaign—marked a setback for District Political, the young political consulting firm run by Rodriguez, Brown, and a third partner, Jaime Alonso. It was far from their first.

When District Political launched last year, it included some of D.C.’s best young political talent. Even after several partners left the firm in late 2015, District Political looked poised in 2016 to put several challenger candidates in District government—or at least to help earn them strong showings. Instead, it’s been on a breathtaking losing streak, with the firm’s last two candidates failing even to make it to election day despite sizable campaign treasuries.

It’s a surprising washout for a young company that comes with political talent and gushing words from previous clients. The big-talking Rodriguez, 35, ran Edward “Smitty” Smith’s 2014 campaign for attorney general, which pulled off a surprisingly successful second-place finish. Smith, who admits he had no name recognition before the race began, lost only after eventual winner Karl Racine poured a massive amount of his own money into the race. 

Brown, just 26, ran the failed 2014 mayoral bid of Ward 2 Councilmember Jack Evans, which raised a whopping $1.5 million. All that money couldn’t overcome Evans’ limp appeal to voters or the internal campaign intrigue between Evans’ old associates and his young staff, but it still outpaced his rivals. Brown also worked on At-Large Councilmember Anita Bonds’ successful Council campaign and worked in her Wilson Building office before joining District Political in May. 

The company’s connections offered little-known candidates like Ward 4 hopeful Leon Andrews access to competitive pools of campaign cash they wouldn’t otherwise have been able to tap. Former Ward 7 Council candidate Ed Potillo says District Political brought in great money for his bid—until the fundraising cut he agreed to kick back was simply too costly.

“I just couldn’t afford them anymore,” says Potillo, who dropped out of the race before June’s Democratic primary.

Defending their dismal record in this year’s elections, the company’s principals tout their support for “underdog” candidates. 

“Our firm is proud of our record of giving underdog candidates the fundraising and marketing support they need to run competitive campaigns,” the firm’s partners say in a statement. 

District Political’s most prominent local client in the most recent election cycle was David Garber, a former Navy Yard Advisory Neighborhood Commissioner and smart growther-about-town who launched an early challenge to incumbent At-Large Councilmember Vincent Orange. Despite his head start, though, Garber soon lost the anti-Orange mantle to later entrant Robert White, ending the primary with less than 15 percent of the vote.

District Political had a more unusual candidate in Calomiris, who likely would never have made it to the Wilson Building because of the baggage that seemed to surprise his consultants. Even before LL wrote about his conviction, the charge had already alienated well-heeled interest groups that otherwise might have supported him against incumbent David Grosso. 

The same can’t be said for Jacque Patterson, the latest District Political client to fall short of even making the ballot. Patterson, a charter school operator and former Ward 8 Council candidate, wanted an at-large seat on the District’s usually sleepy State Board of Education. 

District Political helped Patterson blow out his rivals in fundraising. When decade-long incumbent Mary Lord saw the early campaign finance filings—$32,000 for Patterson compared to her anemic $5,000—she was stunned. With contributions from bigwigs like former financial control board member Alice Rivlin and little competition aside from Lord, Patterson looked set to cruise into the seat.

Patterson and District Political won’t be able to spend much of that money, though, because the candidate never made November’s general election ballot. Lord successfully challenged the legitimacy of his nominating signatures—the most basic responsibility of any campaign—meaning that Patterson can’t compete in a race he could have won.

“That to me is just unforgivable,” says Chuck Thies, a political consultant and the treasurer for Vince Gray’s successful Ward 7 campaign. 

It’s not clear how much District Political, which touts its fundraising prowess, is to blame for Patterson’s inability to gather enough valid signatures. Its partners declined to comment on their role in signature collection, but Patterson certainly isn’t willing to bear all the blame for the embarrassing failure to launch.  

“I think we were wrong-focused,” says Patterson, who adds unequivocally that he wouldn’t hire the company again for any future campaigns. 

With such early misadventures inside D.C., District Political is now focused on races outside the city. The firm’s partners also point to their work on behalf of a nonprofit, as well as the creation with Ward 1 Councilmember Brianne Nadeau of a local chapter of an organization for local elected Democrats. 

Apparently, Rodriguez still has some money to splash out. While LL was reporting this column, Rodriguez called, unbeknownst to his partners, to ask the name of the City Paper employee in charge of ad sales. He went on to ask whether LL would be aware if City Paper suddenly received a lot of money, and pondered how much he would have to spend in ads to gain more “power” to kill stories like this one.

It’s one more offbeat scheme from an outfit that tried to make its name with unlikely candidates. Unluckily for District Political, though, the problem with underdogs is that they tend to lose.

Update, 10 a.m.: According to a District Political statement released shortly after this article was published, Rodriguez is no longer a partner at the firm.