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It took a judge`s order to get Sheila Jackson`s twin 6-year-olds into kindergarten at Oglesby Elementary School.

The Chicago public school system says that`s because the class was overcrowded. But Jackson, in a pending Cook County Circuit Court lawsuit filed on her behalf by the Legal Assistance Foundation, says it`s because she is homeless.

Jackson`s case is one example of how the Chicago school system, already mired in serious financial and structural problems, is coming to terms with yet another pressing dilemma: how to identify and educate the city`s homeless children.

It is a dilemma that school systems throughout the country are mandated to address through federal law. Under the Stuart McKinney Act, passed in 1987, schools are obligated not only to provide a quality education, but also to seek out homeless children and transport them to school.

The foundation`s suit charges the Chicago system and the Illinois Board of Education are failing miserably to fulfill those requirements.

”Homeless children continue to face numerous barriers to access to a comparable, free, appropriate public education,” the foundation said in a report released in mid-June.

Jackson`s children, as well as three other homeless children, were admitted to public schools as a result of an emergency hearing held three days after the suit was filed June 12. Four children were given free bus tokens after the hearing because they had no other way to get to schools where they were already enrolled.

But according to Rene Heybach, a lawyer with the Legal Assistance Foundation, the suit is intended to force the entire school system to adopt a policy that will reach most, if not all, of the city`s homeless children.

”You shouldn`t have to have a lawyer to get into school, even if you are homeless,” Heybach said. ”The suit was filed to try to ensure that the 1992-93 school year will not prove to be the same disaster for homeless children as this past school year.”

In Chicago and other big cities, the problem is particularly acute. The city has one of the largest homeless populations in the country; homeless advocates place the number at between 20,000 and 50,000.

At least one-third of those who roam the streets or shuttle between shelters are school-age children, and experts say the fastest-growing segment of the homeless population is women and children.

For that reason, homeless advocates say, the Chicago school system urgently needs to improve its services to homeless students.

”The only way to solve the problem of poverty is to take the children in poverty and give them an education,” said Richard Roberts, executive director of the Chicago Christian Industrial League, which operates the state`s largest homeless shelter. ”And when you`re at the bottom of the barrel, you have to grab at anything that even looks like light at the top of the barrel.”

School systems throughout the nation have taken various approaches to teaching homeless children. Some send teachers to shelters and assign teachers and aides to work exclusively with the homeless.

The New York City Board of Education has hired coordinators to track down and enroll homeless children, who they believe number between 3,000 and 8,000. In Orange County, Calif., the school board converted two motor homes into classrooms and sent them throughout the county to pick up and teach homeless children. The program reaches about 350 children a year.

But the Chicago Board of Education has only two people on staff whose sole job is to reach out to homeless students. The board`s homeless program consists primarily of public service announcements, mailings and handouts to teachers and board employees, said program coordinator Laverne Davis-Sams.

Teachers and other school employees receive handouts describing homeless children`s rights to an education. Shelters receive packets full of paperwork necessary to enroll children in school, such as transfer forms and applications for fee waivers.

Yet the program places the burden of action more on homeless families than on the board itself or board employees.

Heybach said she spent more than five months in negotiations with Davis-Sams and school administration lawyers, trying to show holes in the board`s program. But those discussions did little more than create animosity between school personnel and Heybach`s staff, both sides said.

In Heybach`s eyes, the injustice is obvious: Children whose parents have fallen on hard times are denied the opportunity to learn basic academic skills.

Parents are misled to believe that they cannot enroll their children in school if they cannot round up birth certificates and medical records-documents that, more than likely, were left behind at the home of an abusive spouse or disappeared along with the families` other possessions.

And as families claw their way back up the economic ladder, they are moved around among various shelters or transitional housing sites, while their children are bumped from school to school, neighborhood to neighborhood.

Although the board may think it is fulfilling its obligation, Heybach said, individual schools are not following through on their obligation.

”I think there are a lot of good people in the system. But if they`re not trained properly, it doesn`t matter,” she said.

Operators of homeless shelters say they know from experience that in spite of the board`s outreach program, homeless parents still face major obstacles in enrolling their children in public schools.

Most homeless families cannot afford the cost of transporting their children, and not all school personnel have enough knowledge of their own system to point families to where they can tap into board resources, said Sandy Ramsey, director of Corner Stone Community Outreach, which runs a homeless shelter.

”The problem is that when you go to the school, either A, they don`t know what you`re talking about, or B, it`s too time-consuming,” Ramsey said. ”The first response is that they don`t furnish tokens, because they don`t know they are supposed to.

”We had a family that came . . . and we paid for the tokens to send the kids to school for the remaining week and a half of the school semester. We didn`t want to have to go through the red tape and paperwork of trying to get the school to supply them.”

Madeline Killingsworth, who has lived in three homeless shelters, said she was never offered any transportation for her 7-year-old son, Roland. Killingsworth said she accompanied her son on an hourlong bus trip to school from the shelter every morning.

On days when Killingsworth could not round up enough money to take the bus ride-which included three transfers-Killingsworth said Roland had to miss school.

”Nobody ever mentioned anything about transportation to us,” she said.

In addition, many shelters have time limits for how long a family may stay. Families are forced to move to new shelters, sometimes across town, and are left with not only expensive bus fare, but also the difficulty of tracking down their records.

The situation is not entirely bleak. Some shelters go to great lengths to get children into school, like Ramsey`s shelter and Clara`s House, run by Clara Kirk.

”One of the demands at Clara`s House is that for every woman here with a school-age child, they must have that child in school,” Kirk said.

And Carolyn, a 12-year-old who lives in a shelter, is one example of a child who found her way back to school while living in poverty. She became homeless after her mother, Christine, 34, who asked that the family`s last name not be used, was forced to move to Clara`s House.

Carolyn missed several days of school when her family became homeless. But she said living in a shelter gives her a renewed appreciation for school. ”I really like school,” said Carolyn, whose grades suffered for a while after becoming homeless, but improved after she found her classroom a haven, for at least part of the day, from her situation.

Some individual schools make extra efforts to identify, transport and educate homeless children. Burley Elementary School, in the Lakeview neighborhood, is characterized by transiency and had 29 homeless children pass through its 1st-grade class this year, said Principal Barbara Lewis Gordon.

Just down the street from the school is Church of the Reconciliation Shelter, which provides housing for homeless families for up to four months-less than half the length of a normal school year.

When the time comes for the families to move out of the shelter, Gordon said, she sits down with each of them and tries to find out whether staying at Burley would be the best situation for the children.

But although Gordon understands her role in fulfilling the Stuart McKinney Act, a number of other principals may not. And Gordon said it`s not their fault, because they are not getting clear direction from the board`s central office.

”The restructuring of the Chicago public school system that has been done in the guise of reform has brought about a breakdown of communication and great confusion,” Gordon said.

Even Davis-Sams acknowledged that the central administration cannot monitor every school and ensure that every homeless child in the city receives a quality education.

”People will fall through the cracks, intentionally or unintentionally,” Davis-Sams said. ”But the only thing we can do is make the information available to the schools and take it for granted that the professionals will do their job.”