Editor’s Note: Medill reporter Shane Shifflett offers a first-person account of covering the story of Anna Green, a mother, former addict and Cook County inmate seemingly lost in the county’s bureaucracy

On Mother’s Day, Anna Green didn’t see her kids. She didn’t go out with family or friends. Anna spent Mother’s Day this year in the Cook County Jail. And for 15 minutes I was there with her.

Anna filed into the visitation room with a procession of eight or so other inmates. Their faces were impassive while walking into the room, but as each prisoner locked eyes with a familiar visitor, each face beamed a grin-except for one. Anna Green kept her eyes wide, scanning the room for someone, anyone she might recognize. All she knew was that she had a visitor.

She had no idea I was coming. She had no idea who I was.

But I knew a lot about her. I had become aware of her while attending a community meeting in Uptown on the North Side about a month earlier. Her case is one that residents considered of importance, and with her 300th arrest for prostitution occurring in their neighborhood, it’s not hard to understand why. The residents’ general feeling regarding Anna is that enough is enough: they saw a woman they wanted out of their neighborhood.

I saw a system that worked without solving anything, without satisfying anyone, without helping anyone, and decided to investigate. That led me to spend part of Mother’s Day in jail to deliver Jeffry Mandell’s phone number to Anna.

I personally contacted Mandell, a Chicago criminal defense lawyer with more than 40 years of experience. The more I learned about the way the criminal justice system keeps a bed warm for the chronic drug abusers, the homeless and the mentally ill of Chicago the more I wondered whether Anna’s case could end differently. After discussing Anna’s situation with him, he offered to represent her for free.

But there was a hitch.

Because of ethical obligations, Mandell couldn’t offer his services without Anna contacting him first. And because it was against policy to deliver information to inmates, no one at the Cook County Jail could forward the phone number to her for me. And because Anna’s May 11 court date was rapidly approaching, mailing her the information wasn’t an option.

The system left me with no alternative but to go to jail to try to see her.

As Anna searched for a familiar face, I was also trying to figure out who I was looking for. Even though I had a black and white photocopy of her mug shot, I wasn’t sure I could spot her. In addition, my nerves were on edge.

Hard stares and sideways jokes

Even though I walked into the Cook County Jail a free man and my status hadn’t changed on entering, the demeanor of every guard I encountered was cold enough to make me wonder whether I’d be able to leave.

Hard stares and sideways jokes gave me the feeling that even a slight infraction against some deeply buried rule would be reason enough to throw me in the stockades.

I waited until everyone else was seated and deep into overdue conversations. I raised my hand but she hesitated. A look of pregnant worry crossed her face for a moment as if I was signaling her by mistake. It wasn’t like the movies. Although glass separated inmates from visitors, there weren’t any phones or dividers between the sets of stools. No illusion of privacy. The room was crowded, and in front of each stool was a device that looked like a speaker that also doubled as a microphone.

To hear her, I had to press my ear up against it.

I expected her, after years of drug use, to be hardened and disjointed. Once I explained myself, she warmed and became animated. She was eager and full of questions. Sometimes animated, sometimes soft-spoken-she appeared pleased that someone seemed to care. Her story at points seemed genuine; at others, it sounded as though it had been told before.

Anna maintained that she didn’t do anything wrong when she was arrested this time but she acknowledged her history made that stance difficult to defend.

She said prosecutors wanted her to serve two years in the penitentiary-a fact later confirmed by Mandell-and that she didn’t know what her public defender was doing to help her. My repeated attempts to speak to someone associated with her case or with supervisors at the office were unsuccessful. Mandell later said that the public defenders were planning to accept a deal from the judge for a one-year sentence.

As Anna lamented her situation-about days wasted, about a family she’s estranged from, about a situation, she admits, is of her own construction-tears started to stream down her cheeks.

“I’m about to turn 45,” Anna said. “I lost my life to them drugs.”

Stifled by bureaucracy

Mandell had mentioned a court program for drug addicts offered by Circuit Court Judge Lawrence Fox.

Fox’s program, officially known as Rehabilitative Alternative Probation, or RAP, is designed to keep the convicted out of prison so long as they abide by some strict guidelines and submit to an intense drug treatment. But it didn’t sound to me as though the public defenders were working that angle.

So I said goodbye to Anna and headed out to the officer controlling the visitors’ paddock.

Because of the glass separating us, I was unable to pass Mandell’s number to Anna. She was interested and had asked me to give it to a guard. I asked the officer to pass Mandell’s number on to Anna but protocol prohibited that. After a few calls to the sergeant and an explanation as to why the information was urgent, they agreed.

By May 11, Anna had contacted Mandell and he was officially representing her.

Mandell attempted to have the case transferred to Fox’s court so Anna could participate in the RAP program. Without a pending drug conviction she was ineligible- another example, in my mind, of how the system works and fails at the same time. Mandell got wind of another program aimed at helping prostitutes; it wouldn’t be ready until the end of the year, if at all.

Stifled by bureaucracy and with no prospects of treatment inside the system, Mandell requested that a decision on Anna’s case be delayed until May 25. The continuance was granted so Anna could at least finish her drug program in the jail.

If, on May 25, 10 days after her birthday, Anna accepts the judge’s offer of one year in jail, she likely will be released immediately based on the amount of time she has served.

“The purpose of me representing her is to try to get her some long-term help so she won’t be back in the same situation,” Mandell said.

But from my perspective, long-term help isn’t an option in Anna’s world.

Anna, whether deserving or not, is subject to a system apathetic to change and solution. In one way or another, we’re subject to the same mandates and decrees that Anna is. We all pay to incarcerate our criminals with time, money, or pain-and sometimes all three. The justice system never fails to leave at least one party, if not everyone involved, disenchanted and unfulfilled by the results it produces.

Her situation isn’t one that needs empathy but reason.

Her trials don’t need numbers or advocacy or opinion to draw recognition.

I could walk out on the street and find any number of people to condemn this woman, mother of eight grown children, on principle alone. I could also pick out a study and throw some numbers on the page that signify a trend in Anna’s favor: graphs and numbers that allow for a detached perspective to consider the trajectory of Illinois or Chicago or even society.

But when we encounter a situation that is as wasteful and costly, and senseless, as arresting someone 300 times, is any of that really needed?