Candidate: Vincent Gray
Why he can win: A late entry suddenly has a huge head start. Sure, he may get indicted for alleged 2010 campaign-finance violations. But a criminal conviction didn’t stop DC voters from re-electing Marion Barry.
Why he won't: If the feds clear him, the mayor looks like a micromanager who had no idea dirty cash was funneled into his previous campaign. If they don’t: He’s no Marion Barry.
Candidate: Tommy Wells
Why he can win: The Ward 6 councilman’s ethics platform may allow him to inherit the frontrunner mantle if Gray goes down. And he’s working social media hard to reach young voters.
Why he won't: If Gray gets a pass, Wells won’t win on his core issues: education reform, transit, and walkable neighborhoods. Or ethics, for that matter.
Candidate: Muriel Bowser
Why she can win: Her Ward 4 is a firm base of middle-class African-American women and white liberals—who can’t miss her imitation of former mayor Adrian Fenty, down to the green tint of her campaign signs.
Why she won't: Her campaign style lacks passion, her record is undistinguished, and people don’t miss Fenty as much as she might think.
Candidate: Jack Evans
Why he can win: Voters may go for his 22 years representing Georgetown and downtown. Just in case, Evans has been spending weekends in Southeast and weekdays cozying up to Barry.
Why he won't: Voters looking for a fresh start may count his experience as a negative. And if a white candidate can win in DC, it won’t likely be one seen as beholden to developers.
Candidate: David Catania
Why he can win: The Republican-turned-independent councilman kept a crucial hospital open in Southeast, and his championing of city schools—he’s visited nearly half as education chair—appeals to middle-class parents.
Why he won't: DC has never elected a mayor who’s white, openly gay, or non-Democratic. Catania is all three.
Candidate: Andy Shallal
Why he can win: The “ABT” (Anybody But Them) bid by the politi-cally progressive founder of the Busboys and Poets restaurants depends on a surge of voter anger over dysfunction.
Why he won't: It’s a long way from an empire based on granola and bruschetta to a $10-billion government. And if ethnicity hampers Evans, Wells, and Catania, it dooms Iraqi-born Shallal.
Candidate: Vincent Orange
Why he can win: His agenda consists mostly of building a 100,000-seat, domed football venue, an indoor water park, and a luxury golf course on the site of RFK Stadium.
Why he won't: Nobody wants that.
This article appears in the January 2014 issue of Washingtonian.