Chicago Magazine on Gangs and Chicago politics:

And though gangs are anything but a monolithic voting bloc, they can, and sometimes do, offer enormous numbers come election time, especially when you count their relatives, friends, and those they muscle at the polls. “An alderman ain’t nothing without the backing of the neighborhood,” says a top-level Gangster Disciple from the South Side. “Without the gangs, it’s hard [for politicians] to exist.”

A Latin King, interviewed at Cook County Jail, recalls how the top leader of his gang, the Corona, ordered every member in his area to vote for Ricardo Muñoz, the 22nd Ward alderman. “Every chapter had to vote for that guy, anyone who was eligible to vote,” says the Latin King. “That was a direct order. That means you can’t say no. If you do, you face a violation”—typically a beating, or worse.

He estimates that the gang delivered hundreds of votes, maybe even a thousand or more, in one of Muñoz’s elections in the 1990s. Moreover, he says, members were also directed—under the threat of punishment—to pass out campaign flyers for Muñoz and walk around carrying his signs. They were instructed to wear their Sunday best: ties, khakis, trench coats. “No thug clothes,” he recalls.

Later on, the article details direct connections between an Alderman and the leaders of the the Gangster Disciples:

Rahiem Ali died on March 23, 2010, after ingesting a plastic bag of narcotics during an arrest and falling into a coma. (As he lay in the hospital, [the Alderman's son] Brendan Shiller represented him in court on charges of aggravated battery to a police officer and resisting arrest.) Ali’s death was ruled an accident by the Cook County medical examiner. Helen Shiller, still the alderman of the 46th Ward, reached out to the family, giving $200 to his mother the day before services were held at a West Side funeral home. The official record categorizes the expenditure as “community outreach–funeral expenses” from Citizens for Shiller, her campaign fund.

That a sitting alderman would help pay for the funeral of a notorious gangster shows how the interests of politicians and gangs can intertwine. For the Ali twins, the connection conferred an above-the-law aura. For their mother, it offered the opportunity to work in the community as part of the alderman’s inner circle. For Shiller, the relationship seems to have brought street cred and political muscle that helped her fend off tough challenges at the ballot box.