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The police officers were in a squad car in October 2007, patrolling a section of Uptown some call a walking pharmacy, where drugs are sold openly. When they saw a silver Chevy Cavalier roll through a stop sign, they ran a check on the plates and discovered that there was a warrant for the arrest of the owner. They approached the car. One passenger turned out to be Rahiem Ali, a 29-year-old Gangster Disciple with a criminal record dating back to 1995 and a rap sheet with nearly 40 arrests. Ali and his twin brother, Rahmon, were well known to police. The two ran a lucrative Uptown drug spot and were notorious for being among the biggest, baddest gangbangers in the neighborhood. According to the officers’ report, they saw Ali shove a hand into his pants pocket and pop something into his mouth.
When they ordered him out of the car, Ali shoved the police aside and ran. It took four officers to subdue him. One suffered a cracked tooth when Ali hit him with his elbow. Two officers doused Ali with pepper spray before he coughed out two plastic bags filled with 23 smaller bags containing what was suspected to be crack cocaine.
Later, at the police station, two lawyers arrived to see Ali. In any other neighborhood, the officers might not have noticed them. But not in Uptown, not when one of the lawyers was Brendan Shiller, the son of Helen Shiller, the 46th Ward alderman.
The 46th Ward is one of Chicago’s most diverse communities, home to the well-heeled and the downtrodden. Throughout her career, from 1987 until she stepped down last year, Helen Shiller was known as a fierce advocate for the latter. Few aldermen on the City Council have been more resistant to gentrification or more likely to embrace social welfare programs. In Uptown, large public housing complexes were a source of pride for Shiller, who trumpeted how they added diversity to the ward and provided a rare commodity on the North Side’s lakefront: affordable housing.
Her critics, meanwhile, argued that the complexes bred and fostered a criminal population, and they accused her of not doing enough to stop the drug and gang violence that dominated specific buildings. During meetings with the police department’s command staff, says a high-ranking police source, Shiller “never [made] a big push to go after any kind of organized narcotic operation.”
Officers working in the 23rd District say Shiller and her chief of staff, Denice Davis, frequently came into the station after certain Uptown residents were arrested to try to defuse things. Police say Davis’s interference on behalf of gangbangers and the Alis—whose mother, Aqueela, was part of the alderman’s political organization—had a chilling effect on their policing efforts. What was the point of making an arrest when it brought trouble from the alderman’s office? “Certain officers would get the message: ‘Maybe I shouldn’t make this stop’ or ‘Maybe I shouldn’t investigate this,’” says Joe Cox, a veteran officer from the district who retired in 2010.
Shiller says she “didn’t have a relationship” with either of the Ali twins, nor did she offer any assistance to them. “My relationship was with their mom. I knew she had sons that had difficulties. I didn’t interact with them. I didn’t know them.”
As the Ali brothers collected thousands a week running the drug spot around Lawrence Avenue and Sheridan Road, word spread among the police to treat the two with kid gloves. A police source says that during arrests, the twins would say, “I’ll have your job. Do you know who my lawyer is? Do you know who his mama is?” The source adds, “They would mention the alderman by name. They would mention Brendan Shiller by name.”
Police and Shiller’s political opponents suspected that the alderman deliberately turned a blind eye to gang activity in order to bring the gang element into the fold and build up her voting base. “It’s what I like to call the exchange game,” says Sandra Reed, who twice lost elections to Shiller, in 1999 and 2003. “She protects the kids, even when they are doing wrong. She helps the parents. They think she is going to protect them, so they all work for her.”
Some speculate that Shiller helped Aqueela Ali fend off multiple attempts to have her and her sons evicted from their apartment at 920 West Lakeside Place, where rules prohibit criminal behavior by residents. (Shiller acknowledges she helped Ali with “housing issues.”) While it’s not entirely clear what her role was in Shiller’s political organization, Ali served as a poll watcher, an election judge, and a Shiller campaign worker since at least 2002, campaign records show. Records also show that she gathered petition signatures to get Shiller on the ballot in 2003 and 2007.
But it may have been Ali’s choice of residence that provided her with the most political firepower. Her building is one of the largest Section 8 facilities in Uptown, home to between 800 and 1,000 residents. Ali had clout and the ability to sway public opinion. She was the leader of the building’s tenants’ association board and, perhaps most important, the mother of Rahiem and Rahmon. “You’re talking about the mother of the most well-known gangbangers in the neighborhood,” one officer says. “When she knocks on someone’s door, do you think those people are going to say no?” (Ali did not respond to requests for comment.)
In a ward where the difference between winning and losing can be a few hundred votes, an election can turn on a campaign’s ability to win particular blocks or buildings. For example, when Shiller was first elected alderman in 1987, she won by just 498 votes. In 2007, her last election, she beat the challenger, James Cappleman, by a mere 700 votes, fewer than the number of residents living at 920 West Lakeside.
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, 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.