State Street between 58th and 59th isn’t in the best shape. Empty buildings and empty lots dominate the block, and the cracked, faded asphalt makes it pretty clear that the Department of Transportation doesn’t consider maintaining this particular street a high priority.
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Smith’s celebrity is a double-edged sword in this context, though. Incumbent 20th Ward alderman Willie Cochran, a former Chicago cop backed by City Hall insider and key Daley ally Leon Finney Jr.—cofounder longtime president of the social-services nonprofit the Woodlawn Organization and still CEO of its private real-estate arm, the Woodlawn Community Development Corporation—knows that rappers aren’t usually seen as selfless public servants, even in overwhelmingly black communities like the 20th Ward. In a Sun-Times interview published the same day as Smith’s press conference, Cochran called him a “known hip-hop artist who degrades women and promotes violence in his videos.”
Anyone who’s heard Smith’s music knows he’s aesthetically and ideologically miles away from gangsta rap. I’m pretty sure I’ve seen every one of his videos, and I haven’t spotted a single booty dancer. After UK prime minister David Cameron, at the time an MP, decried hip-hop for inciting violence, Smith arranged a meeting with him to advocate for its socially conscious side. But even if this “known hip-hop artist” can convince voters he’s not a thug, he still has to persuade them he’s more than a naive celebrity running to flatter his vanity.
The day after Smith’s press conference, Andrew Barber of Fake Shore Drive, the most influential locally focused hip-hop blog in Chicago, responded incredulously to the flood of coverage: “Has an Alderman EVER gotten this much press?” Well, sure. Willie Cochran’s predecessor as 20th Ward alderman, Arenda Troutman, got a lot of it when accusations that she’d taken bribes derailed her campaign and handed the 2007 election to Cochran—and she got more in 2008, when she went to jail for mail and tax fraud. But it is possible that no mere candidate for alderman has ever come out of left field and attracted so much attention so quickly. Smith’s task is to turn that attention into enough votes to beat Cochran and any other challengers who may arise. The application deadline isn’t till November 15, but candidates need to collect just 143 signatures to get on the ballot—2 percent of the ward’s turnout for the 2007 aldermanic election, which in the 20th Ward was 7,134. (That might sound low, but only a third of all wards cracked 10,000 that year.) One fellow first-time office seeker, George Davis—a sales executive for his father’s finance company, a block-club vice president, and a member of the steering committee of the Woodlawn Neighbors Association—passed out campaign fliers at Exclusively Yours after Smith finished speaking.
