David Grosso has that look crazy people get when they’re absolutely convinced a miracle is about to happen. The expected miracle: Grosso will upset At-Large Councilmember Michael A. Brown in November’s election.

Conventional wisdom says the little-known Grosso, a vice president at a health insurance company and former council staffer, doesn’t have much of a chance. The charismatic Brown is the well-known son of the late former Commerce Secretary Ron Brown, the first African-American head of the Democratic National Committee. The name “Michael Brown” is so popular that Council Chairman Phil Mendelson had to expend considerable effort educating voters in 2010 that his opponent, a doughy white guy named Michael D. Brown, was not, in fact, Michael A. Brown. Grosso, a less doughy white guy, will be facing the better-known Michael Brown in an election expected to draw heavy black turnout as President Barack Obama seeks re-election.

But Grosso, 41, seems frustrated when others can’t see the obvious path to victory that lies before him. Brown is imminently beatable, Grosso says, because D.C. voters “are tired of the bullshit.” That bullshit includes a series of federal investigations that’s lead to two councilmembers stepping down and pleading guilty to felonies, as well as three guilty pleas from people connected to Mayor Vince Gray’s 2010 campaign. Brown hasn’t been caught up in any of those scandals, but his reputation took a hit when the D.C. Council undid a signature legislative accomplishment—legalizing online gambling in the city—over concerns that the measure hadn’t been properly vetted. And while he’s not been accused of any improprieties, Brown is battling his own campaign finance irregularities, after his former treasurer allegedly stole an untold amount from the campaign account.

“If you want change and reform in your city, I’m your only option,” Grosso says.

The at-large race will likely be the only contest worth watching come November, as there’s little competition for the other seats. Grosso, who has raised a respectable but not impressive $85,000 so far, might be able to mount a real challenge.

Grosso’s D.C. bonafides include spending his teenage years living with his mom at a hippie/Catholic group house on Georgia Avenue NW called the Assisi Community (he went to a Catholic high school in Fairfax County), working five years at Colonel Brooks’ Tavern in Brookland (where he currently lives), graduating from Georgetown Law, and working for both former Ward 6 Councilmember Sharon Ambrose and Del. Eleanor Holmes Norton.

He met his wife while volunteering in San Antonio, Texas. Grosso says he’s been inspired to go into public service by his socially conscious mother, who he says he’s bailed out of jail following protests on several occasions. “She’s the kind of person who doesn’t mind banging her head against a big wall,” he says.

Grosso has never sought public office before. He says the “disrespect for the city” shown by former Ward 5 Councilmember Harry Thomas Jr., who resigned and pleaded guilty to stealing more than $350,000 in city money, inspired him to run on a platform of ethics reform. (He’s also pro-education reform, pro-smart economic growth, and pro-more efficient budgeting.)

But if Grosso, a former self-described “awkward Deadhead,” was inspired by idealism, his tactics are a bit more calculated. Voters will pick two at-large members in November’s election, but it gets even more complicated than that. D.C.’s Home Rule Charter effectively mandates that two of the four at-large councilmembers not be Democrats, a rule that lately has mostly inspired candidates to change their registration, rather than voters to pick from alternative parties. Non-Democrats can come in a distant second and still wind up on the council. Both Brown and Grosso became independents to try to win elections: Brown switched before winning with less than 20 percent of the total votes cast in 2008; Grosso switched from a Democrat to an independent last summer. He says he doesn’t have any problem dropping the “D” by his name to be more competitive.

“It’s D.C. This is our process,” he says.

Grosso is trying to peel off voters who might be keen or indifferent to Brown but don’t like Councilmember Vincent Orange, the registered Democrat in the race, who is expected to win the most overall votes on Election Day. Knocking on doors in Wards 2 and 3, Grosso says, he often doesn’t get past “Hi, I’m David Grosso, and I’m running against Vincent Orange,” before he’s cut off and told he’s just won a voter’s support.

Orange, who did not respond to a request for comment, hasn’t been accused of any wrongdoing. But he has ties to many of the players involved in the federal investigation of Gray’s campaign, including being one of the biggest recipients of Medicaid contractor Jeff Thompson’s donations. Thompson allegedly funded straw contributions to help Gray win; he also gave Orange several money orders in 2011 that Orange himself says look suspicious.

Despite those ties, Orange dispatched similar reform-minded candidates Sekou Biddle, Bryan Weaver, Peter Shapiro, and Republican Pat Mara in elections the last two years. But for Grosso, the beauty of D.C.’s system is that he can run against Orange without actually having to beat him. Grosso hopes to get the second votes on any ballots from the city’s 30,000 Republicans who support GOP candidate Mary Brooks Beatty. Other candidates include Leon Swain, the former head of the D.C. Taxicab Commission, who worked undercover for the FBI for two years on a bribery case, and A.J. Cooper, a former BET host.

Another calculated move on Grosso’s part: a recent challenge against Brown’s petition signatures that could kick Brown off the ballot. Grosso says just less than half of Brown’s submitted signatures are illegitimate. (Longtime civic activist Dorothy Brizill has filed a separate complaint, saying Brown’s signature-gathering effort looks “pretty bad.” Brizill’s no stranger to petition challenges, having successfully bumped former Mayor Anthony Williams off the ballot in 2002.)

Brown’s staff says he has more than enough valid signatures. The Board of Elections and Ethics will rule on the challenges next month, but even if the board sides with Brown, it’s still a clever move by Grosso to tie up Brown’s already struggling campaign.

In June, police searched the home of Brown’s former campaign treasurer, Hakim Sutton. Sources familiar with the investigation say Sutton wiped out a significant portion of Brown’s campaign fund. Sutton hasn’t responded to requests for comment; he has not been charged with any crime.

Since then, Brown says he’s raised more than $30,000. But elections officials, citing the theft, haven’t required him to file a report saying how much he’s got left to spend. On top of that, one of Brown’s top campaign aides, Kadessa Tribble, has had to take significant time off for personal reasons, Brown says. Brown insists those setbacks are minor and that he’ll have plenty of money and staff come November.

So can Grosso pull it off? If Brown winds up being booted from the ballot and has to run a write-in campaign, Grosso’s chances will certainly improve. Either way, the at-large campaign looks like it’ll be worth paying attention to for voters and fans of political drama alike. Just don’t expect a miracle.

Photo By Darrow Montgomery