Anna Green’s long, aimless drift through the criminal justice system stopped at an intersection on June 8, after she pled guilty to yet another felony prostitution charge.

But the woman, who has been arrested 300 times, may finally be taking a turn in a promising new direction. Judge Stanley J. Sacks, in a Cook County criminal courtroom, sentenced Green to 18 months probation. She was close to leaving jail once again without help facing her demons.

But her lawyer, Jeffry Mandell, negotiated with the judge to get Green into a drug treatment program. Although Green, 45, has a history of drug-related arrests, she says she has never been treated for her addictions. Now she has a choice to make.

“She has to do something to break this vicious cycle, which is drugs and prostitution,” Mandell said. “If she doesn’t, she’ll go to jail for a long time.”

If Green violates the terms of the drug program she is assigned to, she could face up to six years in jail. No date has been set for her to start treatment. Sack’s ruling was a gentle one, considering Green’s criminal history. Her court records date back to at least the late 1990s.

“I haven’t seen worse in my 21 years on the bench,” the judge said.

Green, who has spent most of the past two decades on the North Side, has numerous convictions for prostitution, drug dealing and aggravated assault. She has been stuck in a vicious cycle with no clear exit, according to Mandell.

“Here is a woman who is a poverty victim. What does she have?” he asked. “She has no skills. She can’t work, and the only way she can make money to stay alive is by prostituting.”

Several Uptown residents attended Green’s trial, and at one point they stood as a group to indicate their disapproval of Green’s crimes over the last 10 years. Their message: “Get Green out of Uptown.”

But Uptown, especially near the area of West Leland and North Clifton avenues, is a place where drug addicts and the homeless can get essential services, neighborhood residents acknowledge. Homeless shelters like Cornerstone Community Outreach and Sarah’s Circle provide housing, food or medical services. But they lack the tools to hold the people they serve accountable for actions that disrupt the community.

Tonia Lorenz attended Green’s trial. The view from her Uptown window, she said, has been polluted by drug abusers, users, and prostitutes. She has even observed Green, addled and in vulgar discourse, from that window. Despite her desire to clean up her neighborhood, Lorenz and others who attended the trial also want Green to clean up her life.

“We all wish her the best for many reasons,” Lorenz said. “I just can’t see her succeeding in Uptown.”

During her probation, if the court does not assign Green elsewhere, she might be evaluated by Treatment Alternatives for Safe Communities. A state-approved agency, it monitors drug addicts and assigns them to treatment programs. The agency will probably assess Green and determine if she does have a drug or alcohol problem. If so, they will assign her to a specific treatment program. That could range anywhere from intensive intervention at a residential facility to a much less structured program of weekly visits with treatment coordinators.

Treatment Alternatives says the cost per person for managing and treating a client is $19,000 cheaper than a year’s stay in prison. But homelessness amplifies even small problems.

“If a person is worried about where they are going to sleep it will make it hard to focus on recovery,” said Daphne Baille, the agency’s communications director.

Before Green goes to treatment, she may have to finish the remainder of a previous sentence. She was arrested while on parole, and information regarding her status wasn’t yet available. Green now has a chance, however slim, to make a better life for herself.

But her case is just one example of a criminal justice system that doesn’t always work to help the hopeless.

“Sending her to the pen has done nothing,” Mandell said.