CHICAGO (AP) — The award-winning rapper who wants to be a Chicago alderman looked down the block and counted up the boarded houses in this slice of the city’s South Side. One. Two. Three. Four. Five. Six. Seven. Eight.

“How can you walk here and not feel something in your heart? We’re living in an urban ghost town,” Che “Rhymefest” Smith told The Associated Press during a van tour of the ward where he lives. “I see two things. The first is neglect. The second is opportunity.”

In a landmark year for Chicago politics, the winner of a 2004 Grammy is running an unorthodox campaign for City Council. His street-wise lyrics have given him a youthful following, in Chicago and beyond, but it’s more than his fame that gives him a shot at winning. In a field of five candidates, he’s picked up support from the powerful Chicago Teachers Union and several political experts say a victory Tuesday or making an April runoff vote are quite possible.

The presence in a council seat of Rhymefest — a broad battle rapper who once went toe-to-toe with, and many say easily defeated, Eminem — would certainly shake things up in a body seen in recent years as a compliant rubber stamp for retiring Mayor Richard Daley.

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“He’s a homegrown advocate with a heart for his people,” said Stacy Davis-Gates, a spokeswoman for the teachers’ union “He’s a hip hop artist, his initial expression is to champion the oppressed and inspire transformation.”

But he’s far from alone in his vision of bringing change and opportunity to Chicago politics. A record number of people — nearly 250 — are seeking council positions and major changeover is expected. Experts predict up to 20 new aldermen on the 50-seat council and a likely power shift. That means mayoral candidates like former White House chief of staff Rahm Emanuel would face an unpredictable and likely more independent City Council.

Rhymefest paints himself as an alternative to business as usual for the 20th Ward, which includes some of the poorest and highest-crime areas of Chicago. First-term Alderman Willie Cochran, who faces a groundswell of opposition, was elected to succeed former Alderman Arenda Troutman. She was sentenced to prison in 2009 after pleading guilty to taking payoffs and campaign contributions from developers in return for zoning changes.

The 33-year-old rapper — named Che after the 1950s Cuban revolutionary Che Guevara — has pledged to give up a portion of his aldermanic salary for loans to bring business to the area and says he’ll only serve two four-year terms. His campaign headquarters are inside a dingy car wash surrounded by vacant lots, and some of his fundraisers have been held at nightclubs where he performs.

Rhymefest has received praise from Princeton University scholar Cornel West and rapper Kanye West, with whom he shared a Grammy for co-writing “Jesus Walks.”

Though born in Missouri, his family has lived in Chicago since the 1960s. He attended city schools and Columbia College downtown. His wife is a teacher for Chicago Public Schools. He gets respect in mainstream rap circles, but has also taken time to attend nonpolitical events with local grass-roots hip hop artists. And though he rarely discusses it publicly, his faith has been a central part of his life; the rapper became Muslim after years of study.But he’s also got a criminal past, something that’s caused him some trouble on the campaign trail. Rhymefest was convicted in 2001 for domestic violence involving his first wife and in 2005 for firing a gun following a dispute with a real estate agent in Indiana. Those incidents came up at a recent candidate forum including former police officer Cochran, lawyer and businessman George Davis and a pastor, the Rev. Andre Smith.

“Our children are dying on the street and anybody can make a platform to make themselves look good. No disrespect, but rapping, beating women and shooting at realtors … ” Smith said before the crowd booed him into stopping.

Rhymefest, who sat in silence and rested his face on his hand, appeared angry.

The rapper says he’s learned from his past, insists he’s changed and that others can benefit from his perspective. He’s says he’s happily remarried and has two kids, including primary custody of a son from his first marriage.

“We’re telling people because you made a mistake when you were younger you can never take a position of leadership? You can never grow out of it?” he said. “Then what we’re telling the 20th ward is, lay down and die, you’re done. We have attorneys on the City Council and that doesn’t mean we were able to avoid a city deficit. We have officers who are aldermen, that doesn’t mean our communities are kept safe.”

The other candidates in the race have said Rhymefest does bring good ideas.

Davis, a community activist who was endorsed by both the Chicago Sun-Times and Chicago Tribune newspaper, agrees he and Rhymefest have similarities. Both of them have made public safety, housing and attracting business among their top issues for the ward, which includes Washington Park, Daley’s proposed site for an Olympic stadium in the city’s failed bid for the 2016 Games.

But Davis says that Rhymefest and other candidates don’t have the experience to manage the city’s roughly $6 billion budget.

“There’s a lack of any vision or lack of foresight or any forward thinking to solve the challenges we have,” Davis said. “We need someone in the 20th ward that has the ability to be a thoughtful leader.”

Cochran has seen a groundswell of opposition and the police union didn’t make an endorsement in the 20th, though it generally backs police officers. He defended himself at a recent candidate forum, saying he cares about the ward, but navigating the system isn’t so easy.

Even those who don’t support Rhymefest, like 73-year-old Gloria Searcey, say he understands issues in the ward like a lack of hospitals and business development. The retired furniture store worker has lived in the area since the 1940s and has seen it fade from a vibrant community with a busy shopping corridor to one of the most neglected areas in Chicago.

But even if Rhymefest loses, his ward and Chicago will likely stay a source of inspiration for his music. While driving around the area, Rhymefest discussed his frustration with poverty and how he felt those at City Hall had given up on his neighborhood.

He then broke into an impromptu rap, bobbing his head from side to side and chopping the air with his hands.

“Givin’ up on the hood, I’m not down with it,” he rapped. “We all in a pool of debt and just drowned in it.”

Copyright 2011 The Associated Press.