We’re all suckers for the outsiders and underdogs in political races. We all know them — the candidates who don’t already occupy an elected office, who seek to break into the system instead of merely moving up in it. They threaten elected coups, promising to move into office and shake things up like only an outsider can.

And so we meet Michael Brown, the self-styled outsider of the District’s mayoral contest. Tall, well-dressed, bald-headed and quick to crack a smile, Brown seems to relish the opportunity to take on the three of his five opponents that currently serve on the D.C. Council — Adrian Fenty, Linda Cropp, and Vincent Orange. “When you’re on the council, you’re perceived as part of the problem,” he told DCist in a recent interview. And to bolster his case, he notes that history has sided with the outsider more often that not in District mayoral races — “Of four mayors,” Brown notes, “only one came from the council.”

And even though Brown has so far been out-fundraised — a January 31 filing showed he had raised $106,978, substantially less than his insider competition — he doesn’t see this as a liability. Brown proudly states that when he announced his candidacy, he did so by travelling to all eight wards using public transportation, and has since knocked on doors and stood outside the Anacostia Metro station at night to meet voters. “We’ve become the grassroots community campaign,” he tells us.

But how far can Brown go as an outsider? Will voters respond to his calls for City Hall to be cleaned out, or will they instead rely on seasoned political operatives like Fenty, Cropp, or Orange to take over where D.C. Mayor Anthony Williams has left the city?