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Arrested 396 times, woman knows how to work the system

A video screen capture ShermaMiles woman who has amassed nearly 400 CPD arrests since 1978 | Ting Shen~Sun-Times

A video screen capture of Shermain Miles, a woman who has amassed nearly 400 CPD arrests since 1978 | Ting Shen~Sun-Times

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Updated: December 20, 2013 11:10AM



On a sweltering day last summer, traffic came to a standstill on a bustling stretch of Bryn Mawr Avenue in Edgewater, emergency crew sirens wailed and Chicago Police Officer Tom Rolon hurried to the scene.

The crackling voice in Rolon’s radio reported a woman foaming at the mouth and lying in the middle of the street; Rolon approached and instantly recognized her.

“She looked up at me and says, ‘Officer Rolon, I love you,’ ” recalled the now retired cop, who spent 17 years on foot patrol in Edgewater. “She got up, and all of a sudden she’s OK.”

Rolon recognized Shermain Miles because he’s seen her more times than he can count — drunk, half-naked, cursing and, on one occasion, lunging at another woman with a dinner fork.

Since 1978, Chicago Police alone have arrested Miles 396 times, mostly on the North Side — under at least 83 different aliases. Those arrests include 92 for theft, 65 for disorderly conduct, 59 for prostitution-related crimes and five for robbery or attempted robbery.

The frustrating truth: The system — strapped by overcrowded prisons and cuts to mental health funding — hasn’t been able to save Miles from herself or to help the communities she menaces. Nothing has worked. Not jail. Not prison. Not countless psychological exams for the woman described as being “acutely psychotic.”

Miles is a master at working the system, says Rolon. She fakes seizures that mean costly hospital visits. She gets judges to delay her cases. And then she returns to the streets to be arrested again and again — so many times that she ranks in the top 1 percent for all current CPD arrestees.

To the relief of many, Miles, 51, is currently in prison in downstate Lincoln. Police arrested her last August, when — after a day of allegedly slapping, punching and generally harassing folks on a stretch of Broadway in Uptown — she is accused of chasing after Ald. James Cappleman (46th). That arrest landed her back in prison for a possible parole violation of a 2010 conviction for robbing a 75-year-old Bosnian immigrant at knifepoint.

On Tuesday, the Illinois Prisoner Review Board is set to decide whether Miles violated the terms of her parole; if she did, it’s likely she’ll be held until April 2014, when her parole expires.

Mujo Cesic, Miles’ victim in the knife robbery, wants another option.

“She should never be released,” said Cesic, a firefighter in his native Bosnia who spoke through a translator.

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Miles spent her childhood dodging feet, fists and anything else her mother found to inflict pain.

“We were all abused by my mom, but Shermain was abused more than any of us,” said one of Miles’ two sisters, who lives in the Southwest suburbs. “It’s the root cause of all her problems.”

The sister — who didn’t want her name used — said the state ultimately plucked her and her sister from their home in the Cabrini-Green housing project. Their mother died in 1994, and the sister said she never knew their father.

Unlike her sister, Miles never adjusted to foster care. By the time she was 14, Miles’ life on the streets had begun. She got pregnant as a teenager, and has an adult daughter living in Minnesota, the sister said.

How did the sister succeed where Miles didn’t?

“I was put in a good foster home with people who loved me and cared for me,” the sister said.

At some point, Miles drifted to the North Side.

Phelps Holmes probably knows Miles as well as anyone in Uptown — the geographical center of Miles’ territory, which mostly ranges from Lake View to the south and Rogers Park to the North. Holmes is off the streets now, but for nine years he slept in parks and on loading docks — much of that time with Miles slumbering nearby, he said.

“She’s always been a sweet young lady to me,” said Holmes, 59, standing a stone’s throw from the corner store at Sheridan and Lawrence, where Miles likes to buy her liquor.

Miles was generous with her food and drink, but silent on her past, Holmes said.

“You don’t talk about where you come from . . . because sometimes what got you homeless is because of things you did with your family,” he said. “You might have got on drugs and stole from them. They can’t trust you no more.”

Miles rarely sleeps in one of Uptown’s estimated 500 shelter beds because she fights with other guests, Holmes said.

“Steve,” a man who sleeps on a square of cardboard beneath Lake Shore Drive at Wilson Avenue, doesn’t know Miles, but he understands why she might avoid shelters.

“The shelters have bugs in them and they’re overcrowded; otherwise, I’d be in one right now,” said Steve, who wouldn’t give his last name.

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Miles’ run-ins with police started decades ago. Her first arrest in the city came in 1978, for allegedly breaking into a car. Since then, police have detained her for assault, burglary, drug possession and public indecency — among many other crimes. Miles’ busiest year was 1988, when police made 25 arrests. In the majority of those cases, Miles is arrested, released and never convicted; Rolon says that’s partly because Miles knows how to work the system — getting judges to delay cases so that her victims get frustrated, stop coming to court and then the case is dismissed.

The Cook County state’s attorney’s office counts 73 convictions in all.

“We also need her to come to court,” said Fabio Valentini, chief of Cook County’s Criminal Prosecutions Bureau. “You can see that in a great many cases, she fails to appear in court.”

Valentini defends his office’s handling of Miles’ more recent cases, saying that whenever she’s been charged with a felony — 10 times, according to prosecutors — she is convicted. He also says that within the last year, Miles’ cases have been assigned to a single, community-based prosecutor available to talk over concerns with the public and police about Miles’ activities.

On the rare occasion when Miles has served prison time, she benefits from a state law that automatically cuts an inmate’s term in half for a range of crimes; that’s why she served only three years of a six-year term for robbing Cesic in 2008. But in 1993, Miles served about seven months of a two-year prison term — her first Illinois prison stay — stemming from an attempted robbery charge. In that case, Miles received about five months’ credit for good behavior, said Illinois Department of Corrections spokeswoman Stacey Solano.

After Miles’ most recent release from prison in April 2011, CPD arrested her six times before she was finally sent back to prison. Why?

“The Department [of Corrections] makes decisions on a case-by-case basis,” Solano said. “And when appropriate, will try to impose community-based sanctions for parolees before [an] automatic return to prison.”

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Miles has been in and out of mental health hospitals and participated in various programs in the communities she calls home, including Thresholds, a North Side agency that bills itself as the state’s oldest and largest organization helping people with severe mental health illness.

“Within one year of joining a Thresholds program, 90 percent of Thresholds’ members remain out of costly hospital care and nursing home care,” according to Thresholds’ web site.

How the agency has helped Miles remains unclear. Thresholds refused repeated requests to talk about Miles or their programs in general.

Miles has told court-appointed psychologists she believes people are trying to kill her and steal her money.

While signing some forms, “the defendant laughed so loudly and exuberantly that she almost fell out of her chair,” one psychologist wrote in a 2006 letter to the judge handling an attempted robbery case that involved Miles grabbing an Edgewater woman and telling her: “Give me your f---ing money or I will kill you.”

Cappleman, who said he witnessed Miles punch and slap two people last summer on North Broadway before she came after him, says his ward’s notorious resident can’t simply be released from prison without a “highly structured” plan in place.

“For the sake of Ms. Miles and the community, it’s time to take the next step to ensure the community is no longer terrorized by her behavior,” Cappleman wrote in a February letter to the state’s Prisoner Review Board, which will consider Miles’ case Tuesday.

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So what does Miles have to say for herself?

Earlier this year, she agreed in a hand-written note to an interview with a Chicago Sun-Times reporter: “Since I have gave my life over to the Lord, I have no problem with you coming out here. . . . It is very much appreciated that you are wanting to hear my side of the story.”

On the day of the interview, she sat quietly waiting on a bench in a hallway inside the red-brick complex at Logan Correctional Center in rural Lincoln. She wore lipstick and eyeliner, and her frequently unkempt hair was neatly styled. One correctional officer described Miles as well-behaved, requesting Gospel music when she is transported to Cook County for court appearances.

But when a reporter introduced himself, she said, “Am I getting paid?”

When she found out she wasn’t, Miles turned on her heels and walked away, saying: “Then I have nothing to say. Jesus already took care of it.”

Back in Edgewater, the business community in particular is dreading Miles’ possible return. Miles has been known to chase after pedestrians and pinch them. She sometimes walks out in the middle of traffic and holds out her hand like an unofficial crossing guard.

“There is always one case that rallies a community, and she was that case,” said Marko Zaric, a spokesman for The Business People for Bryn Mawr, a group that monitors crime in the area.

Edgewater florist Rick Flinn, who said he called police 25 times last summer about Miles, recalls one frustrated police officer’s approach to handling her.

“There used to be a person who’d pick her up and drop her off on the Far South Side,” Flinn said. “She always gets back here somehow.”



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