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At Michael Brown’s re-election campaign headquarters at 9th Street and Florida Avenue NW, a campaign banner bearing Brown’s name and picture hung outside. Whoever put the banner up didn’t properly secure its top left corner, leaving it to droop noticeably. It wasn’t the biggest deal: Brown’s name was still visible to passersby. But it certainly didn’t look professional. The banner hadn’t been hung with any pride; nor had any campaign workers bothered to fix the obvious problem for several weeks. It looked, in a word, sloppy.

Which was fitting. On Tuesday, Brown lost his D.C. Council seat due to a combination of a messy personal life that spilled into public view and a disastrously disorganized campaign. David Grosso, a virtual unknown, beat Brown by more than 18,000 votes in the race for an at-large seat, though both ran well behind incumbent Democrat Vincent Orange in a contest in which the top two finishers won. (To give that spread some context: When Mayor Vince Gray soundly beat former Mayor Adrian Fenty in the 2010 primary, the margin was 13,000 votes.)

Brown not only lost, he lost big. He got 21,000 fewer votes on Tuesday than he did four years ago, when he was first elected. In some more affluent, predominantly white voting precincts, Brown won fewer votes than an unfunded, unknown candidate from the Statehood Green Party. In working-class, mostly African-American neighborhoods east of the Anacostia River, Brown’s vote totals were far below what they were four years ago.

“We had obviously a soap-opera campaign, and we had a lot to overcome, and we did everything we could do,” Brown told a small group of supporters at his campaign headquarters late Tuesday night, just as the networks called the presidential race for President Barack Obama and U Street erupted in fireworks and joy.

LL’s willing to chalk the last part of that statement up to a late-night pep talk, rather than assume that Brown actually means it. There was plenty more he could have done. In fact, it almost seemed as if Brown did everything possible not to win.

Remember that this was a race that wasn’t even supposed to be close. Brown is the charismatic son of the late Ron Brown, the first African-American chairman of the Democratic National Committee and secretary of commerce under President Bill Clinton. By one measure, his name alone should be worth 35,000 votes. That’s how many a pudgy white guy named Michael D. Brown won when he ran for an at-large seat two years ago against Phil Mendelson (who was elected council chairman Tuesday).

Even in defeat, Brown still had passionate support. Within seconds of his arrival at Plummer Elementary in Ward 7 Tuesday, a woman came up to him and said: “I voted for you because I believe in you.” Another told him that his was the first box she crossed off on the ballot.

All that is part of the reason that when Grosso announced he was running more than a year ago, challenging Brown looked like a fool’s errand. A former aide to Del. Eleanor Holmes Norton and former Ward 6 Councilmember Sharon Ambrose who currently works at a health insurance company, Grosso had virtually zero name recognition citywide.

Plus, Brown had recently been promoted to the head of the council’s influential economic development committee, a perch some of his soon-to-be-former colleagues have used to boost their fundraising.

The conventional wisdom was that Brown would use those advantages to raise a lot of money and win a lot of votes. Helping him out more: the fact that black voters who remembered his father fondly would be turning out in large numbers to help give Obama four more years. After all, even though Brown had switched his registration to independent in 2008 to win one of the two council seats reserved for non-Democrats, he still went to this year’s Democratic National Convention as an Obama delegate.

Sure, there were some warning signs. Brown’s financial and personal troubles have made the papers on a regular basis; despite a healthy annual income of nearly $400,000, he’s faced foreclosure notices on his mansion in Chevy Chase, liens over income taxes not paid on time, and had his driver’s license suspended multiple times. But those are the kinds of problems that candidates have historically been able to finesse thanks to a forgiving D.C. electorate, especially candidates with a record of populist stands on policy issues like affordable housing and job training.

Except this time, the same bad habits that led to Brown’s personal problems bled over into his campaign. Most critical: The $114,000 that somehow disappeared from his campaign bank account over the summer. Brown blames his former treasurer, Hakim Sutton, but Sutton denies any wrongdoing and hasn’t been charged with any crime. Suddenly, Brown’s financial advantage—typically one of the biggest strengths D.C. incumbents have in fending off challengers—was gone. Grosso went into the last stretch of the campaign with more money to spend.

Not that money was the only issue. Supporters say Brown’s effort was disorganized from the start, thanks in large part to Brown’s inattentiveness. He narrowly survived challenges to the required signatures he gathered in order to qualify for the ballot. The $125,000 or so of campaign funds that he spent before the rest vanished did not appear to be put to the best use. Brown’s campaign spent $2,400 a month ($16,000 total so far) on renting the office by U Street. (By contrast, his rent payments in 2008 totaled $900—for the entire campaign—for a space in Petworth, according to campaign finance records.)

That dysfunction manifested itself clearly on Tuesday. Brown’s campaign had almost no presence east of the river in wards 7 and 8, the predominantly African-American areas that helped Brown win in 2008. At many polling locations, the campaign didn’t have workers standing outside handing out literature promoting Brown. Those workers might have come in handy to remind voters that they could pick two at-large candidates, not just one. LL spoke with several voters east of the river who said they voted just for Orange, the Democrat in the at-large race, and no one else. (Unofficial Boad of Elections stats showed that tens of thousands of ballots in the at-large race only picked one candidate. Of course, some of those might have been votes for only Brown, or only Grosso, or for one of the other four candidates.)

By mid-afternoon, Brown was driving himself around to polling places in Ward 7 putting up campaign signs—something that most organizations would have taken care of before the polls even opened at 7 a.m.

“We had more volunteers than anyone else, because we didn’t have the money to pay….I really can’t thank you enough,” Brown told his supporters Tuesday after the results were in. All dozen or so of them.

Meanwhile, at a restaurant a mile and a half north on Georgia Avenue, Grosso’s victory party was packed with scores of volunteers who showed up to work the polls and help their guy win. Grosso says his campaign had 240 unpaid volunteers.

“The two words I got sick of hearing were ‘conventional wisdom,’” Grosso told supporters. “Nobody thought we could win.”

Indeed, Grosso finally cracked the code for knocking off an incumbent councilmember—for the first time since Republican Carol Schwartz lost a primary in 2008, despite a steep recent drop in the council’s popularity thanks to federal investigations that led to two councilmembers resigning and pleaded guilty to felonies.

The Grosso playbook was pretty straightforward. He got in the race early, which gave him time to raise more than $150,000, much of which came from smaller contributions, and establish himself as the anti-status quo candidate. He spent his money wisely, ran an organized, professional campaign, and hammered Brown over ethics every chance he got.

It’s a playbook that will like be studied and emulated during the special election held this spring to fill another at-large seat, the one Mendelson’s election as chairman left vacant. But Grosso’s smartest move can’t be copied: picking Brown as an opponent.

Aaron Wiener contributed. Photo by Darrow Montgomery