The vending machine at H Street NE spot Maketto sells Magnum condoms, cat statues, and pouches of MSG. Elsewhere, diners can buy beard oil and artisanal razors. But last week, Maketto patrons got a chance to spend their money on something not so ironic-chic: a D.C. Council campaign.

On Saturday, Maketto hosted the campaign kickoff for David Garber, the first at-large challenger to incumbent Councilmember Vincent Orange. With Maketto and Garber—a prolific tweeter on urbanism, minor hero of the smart growth set, and natty dresser—a politician and his party haven’t been this well matched since Ward 2 Councilmember Jack Evans launched his ill-fated mayoral campaign at Logan Circle’s tony Le Diplomate.

This is 32-year-old Garber’s first Council campaign, but being new hasn’t made him shy about going after Orange. Garber launched his campaign last week with a video blasting Orange, a pugnacity he brought to his weekend kickoff.

“I’m going to be running against a corrupt politician with deep pockets,” Garber told his would-be donors, by way of hitting them up for his own campaign war chest.

For now, Garber can benefit from entering the race before the June primary and filling an empty field that’s not likely to stay that way. Going against him winning Orange’s seat, meanwhile, is pretty much everything else.

Garber, a former Navy Yard advisory neighborhood commissioner, once covered development (and the lack of it) across the Anacostia River with his And Now, Anacostia blog. Garber is a prolific social media presence with more than 6,000 Twitter followers (and someone at his party recommended his Instagram to LL).

He has the same platform that was big last year, with promises about improved schools and affordable housing. If he’s elected next year, Garber says he’d want to be on the Council’s education or transportation committees.

At Saturday’s kickoff, Garber supporters compared their candidate to Brianne Nadeau, the Ward 1 upstart who wrested away Jim Graham’s Council seat last year by hitting him on ethics and starting her campaign years before the primary. Garber’s campaign is hoping that his early start will help him replicate Nadeau’s success—and that of Councilmember David Grosso, who beat then-councilmember Michael A. Brown by starting his campaign before anyone was thinking about the race.

“I’m excited to jump in early,” Garber says.

Orange hasn’t registered to run again, but tells LL he’ll be back on the campaign trail “at the appropriate time.” At first, Orange’s re-election plans might seem strange, since he’s had the roughest time out of any of the incumbents up for re-election next year.

In 2012, Orange ran interference with health inspectors on behalf of a campaign donor’s rat-filled business. U.S. Attorney Ron Machen then subpoenaed that donor’s records. (Orange says he was just trying to save jobs.) Last year, Orange was fingered in court as the (possibly unknowing) recipient of an illicit Jeff Thompson shadow campaign.

In other words: Orange can’t exactly run on cleaning up the Wilson Building.

Orange also didn’t prove his political talents with his failed mayoral run last year. Like Council colleague Evans, Orange brought in just single percentage points of the vote on Election Day. Unlike Evans, though, Orange’s treasury wasn’t enough to make ward challengers think twice for 2016. Evans raised a whopping $1.5 million in the mayoral race; Orange, who should have a broad contribution base because of his city-wide seat, collected just a tenth of that.

While Orange’s campaigning can tend towards the baroque—think handing out actual oranges and suing after being excluded from a debate—he loves to do it. Orange’s marathon politicking will challenge Garber and the other opponents who will appear in the race, according to former Vince Gray campaign manager Chuck Thies.

“He’s almost the closest thing D.C. politics has to Donald Trump,” Thies says.

Orange also hasn’t managed to anger Muriel Bowser, the one person with enough influence to single-handedly push him out. While Orange had a tumultuous relationship with Gray, he hasn’t made Bowser mad enough to justify her trying to fund an opposition candidate. So far, Bowser has sat out the race, and there’s no obvious Green Team candidate waiting to enter the Democratic field.

Garber consultant John Rodriguez says his candidate is pulling in “very strong” fundraising numbers a week into his campaign, although Rodriguez declined to provide figures. Garber, who’s gay, could could also score some cash from District LGBTQ donors. Currently, the Council doesn’t have any openly gay councilmembers.

On the other hand: Garber is white, running against an African-American councilmember who can get out his votes. The smart-growther types who cheer Garber on haven’t done much to prove their strength at the ballot box lately—as Tommy Wells, the urbanist darling who came in third in last year’s mayoral primary, will tell you.

“If [Orange] were to feel threatened, he is very shrewd at playing identity politics and using that tactic to drive turnout where he needs the votes,” Thies says.

Rodriguez claims that he’s not worried about his candidate’s race hamstringing his chances against Orange, an old hand at the kind of campaign tactics that bring out his voters.

“As we look at the picture today, we’re in a great position,” Rodriguez says.

Photos by Darrow Montgomery