Barbara Byrd-Bennett, the former leader of this city’s troubled public school system, was sentenced to four and a half years in federal prison last week for steering millions of dollars’ worth of school district contracts to her former employer and for scheming to accept kickbacks.

Ms. Byrd-Bennett, who was handpicked for her job by Mayor Rahm Emanuel, learned of her prison term as the almost-cashless district struggles to keep its classrooms open.

Perceived as a seasoned leader of urban schools, with experience in Cleveland and Detroit, Ms. Byrd-Bennett was sought out to improve Chicago’s schools, which enroll more than 380,000 children.

Ms. Byrd-Bennett raised suspicions after the school board approved a $20 million, no-bid contract with her former employer, a private company that provides training to school principals. She had schemed to steer school district business to the company, with the promise of kickbacks and a lucrative job that would be waiting for her whenever she left Chicago. She resigned in May 2015, shortly before being indicted.

“I’m especially sorry that I’ve let down the students and their families,” said Ms. Byrd-Bennett, who pleaded guilty, and who must surrender to a federal prison in West Virginia in August.

Her sentence was more than what her lawyers had requested, but far less than the term of more than seven years that prosecutors had sought. Judge Chang noted the lengthy history of public corruption in Chicago and the school system’s financial struggles as he handed down the punishment.

“When this crime was committed in the midst of the C.P.S. budget crisis, it did make it all the worse,” Judge Chang said.

Chicago Public Schools officials had warned that they could end the academic year on June 1, three weeks earlier than planned, unless the state of Illinois provided more money. Mr. Emanuel backed off that threat on Friday, but said he was not sure where the money would come from.

“We will be here working to find the resources to make all of the other payments we have to make,” Mr. Emanuel said.

The Chicago school district, which serves mostly Black and Hispanic children, has challenged the state’s funding mechanism as racially discriminatory. But the uncertainty was compounded when a judge declined to issue an injunction requested by the city that might have led to a desperately needed influx of cash.

Fear of what might happen if schools closed weeks early prompted the Chicago Teachers Union and others to call for Mr. Emanuel to step in and provide stopgap funding.

“It’s a very precarious and dangerous situation,” Alderman Carlos Ramirez-Rosa.

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