The D.C. Council's Family Business Home rule is now old enough to have spawned a generation of legacy pols. What do they tell us about the District?

At the end of last year, two workers at the Department of Public Works were emailing each other about how rotten it was that Kwame Brown had put the city on the hook for two Lincoln Navigators, returning one because he didn’t like its gray interior.

“My friend I have been down this road before with egotistical politicians who don’t realize there are folks out here who will do everything they can to bring you down,” wrote supervisor Michael Biggs. “Yet, these young brothers like Brown can’t seem to get that in their heads and just march on like they are invincible.”

Two months later, the Navigator incident would be splashed on the front pages of the Washington Post and Brown would be facing the biggest tests of his political career. The episode came not long after the public found out Brown had been sued by multiple credit card companies after running up a large debt on purchases that included luxury cars and a boat called Bulletproof.

Up until the Navigator affair, Brown had lived a pretty charmed political life. He knocked off a highly vulnerable incumbent in 2004, ran unopposed in 2008, and hardly had to break a sweat to become chairman last year.

It wasn’t going to be too long, the conventional wisdom went, before we’d be calling him Mayor Kwame Brown.

“You just kind of knew,” remembers Sam Brooks, one of Brown’s opponents in the 2004 election, of Brown’s mayoral potential. “He’s such, such a good politician.”

If the mayor’s office is in Brown’s future, it’ll be quite a rise for a self-proclaimed underachiever. Growing up with his mother in suburban Virginia, Kwame had behavior problems in school. He failed the 3rd grade and was expelled from his public high school. He went to live with his father and eventually graduated from Wilson High School, where, he says, he rarely went to class.

A compact, restless ball of energy who can ooze charm and flash a megawatt smile on command, Brown has a thorough mastery of retail politics. That’s a big reason for his quick ascension to the second-highest elected position in the District. But he also owes a big debt to the political connections and know-how of his father, Marshall Brown.

Marshall is best known as one of Marion Barry’s most loyal former lieutenants—and for causing a national uproar for complaining about racism after a white colleague used the word “niggardly.” Brown was also a member of the Student Nonviolent Coordinating Committee, the grass-roots civil rights group that served as a launching pad for Barry and several other politicos.

“His gut instincts are just flat-out political,” says Smith, the former Ward 1 Councilmember. “That’s all he ever thinks about.”

Marshall helped conceive and execute Kwame’s first campaign, which out of necessity as much as design followed a grass-roots playbook similar to the SNCC’s. Kwame, who began the race with almost no name recognition and little chance of raising anywhere close to the money incumbent Harold Brazil had, hustled his way to a win by starting his campaign early, knocking on a ton of doors, and planting a lot of yard signs.

Brown family connections who’ve helped guide Kwame’s professional life include Courtland Cox, his former boss at the U.S. Department of Commerce and an SNCC alumnus who also worked for Barry; Tom Lindenfeld, a campaign guru enlisted by Marshall to help with Kwame’s first campaign; and Ivanhoe Donaldson, another SNCC alumnus and Barry aide who’s advised Kwame on campaign issues.

But for all the benefit Marshall Brown has been to his son’s career, he’s also been a burden. His suggestion that the gay rights movement is different from the civil rights movement because “you can choose to be gay” and his recent musings that newer white residents of the District are interested solely in “doggie parks” have hurt Kwame’s efforts to be a seen a politician who appeals to all parts of the city.

Some problems run deeper than glib quotations in the newspaper. The Brown family has attracted legal attention for some healthy paydays it’s won from Kwame’s campaigns. (Marshall declined to be interviewed for this article, calling me prejudiced for referring to him as a Barry lieutenant and insulting me in front of a group of high school journalism students. Kwame wouldn’t talk for this story, either.)

In 2008, an audit found, Kwame’s campaign used an outside vendor to pay his brother’s sales-coaching firm $240,000. Despite repeated requests from the Office of Campaign Finance, the Brown family hasn’t provided bank records to show how that money was spent. The D.C. Board of Elections and Ethics suspects that criminal activity occurred, and the U.S. Attorney’s Office says it’s reviewing the campaign’s finances. Marshall Brown recently told the Post that he takes responsibility for unnamed mistakes.

Marshall may wind up taking the blame for the campaign-finance problems, but the notion that his son also views politics as a means to self-enrichment may never disappear. Whether it does will depend a lot on Kwame’s political skills, as well as the District’s collective ability to forgive and forget.