Man gets 3½ years for robbing student outside Edgewater school

CHICAGO — A 37-year-old man has been sentenced to 3½ years for trying to rob a teenage boy outside a Chicago Public School in Edgewater. David Roosevelt pleaded guilty to attempted robbery before Judge Shelley Sutker-Dermer in exchange for the sentence, according to court records. Prosecutors dropped three additional felonies in the plea deal, including aggravated battery and unlawful restraint.

Roosevelt was on parole for another robbery when he attacked and robbed the 16-year-old boy near George B. Swift Specialty School, 5900 North Winthrop, on October 4, 2022, officials said.

The teenager was walking to school around 7:45 a.m. when Roosevelt, a stranger to the boy, asked him for money. The boy ran away and asked two joggers for help. They, in turn, told him to keep running.

The boy ran to Swift and sought help from a school security guard as Roosevelt arrived on a bicycle, prosecutors said. The security officer intervened in the altercation between Roosevelt and the teen but backed away after Roosevelt “swiped” her arm, according to prosecutors.

David Roosevelt | CPD; Google

During Roosevelt’s bail hearing, prosecutors said Roosevelt hit the boy in the head, knocking his glasses off and causing him to fall to the ground. Roosevelt knelt on top of the boy and repeatedly punched him until others intervened, the prosecutor said, adding that the people who intervened let Roosevelt go as Chicago police officers arrived. Police found him 20 minutes later after another incident.

But CPS vehemently disputed the prosecutor’s version of events.

“The [school] security guard did in fact intervene and was stuck [sic] in the head and then, as she was re-grouping, another staffer intervened. Both of these individuals were trying to keep the child safe,” a CPD spokesperson said in October.

The boy suffered swelling to an eye, facial lacerations, scratches on his neck, and soreness in his head and chest, according to prosecutors.

In addition to the robbery conviction for which he was on parole, Roosevelt was also convicted of aggravated battery in 2020, violating an order of protection in 2014, and carjacking in 2006.

Roosevelt is scheduled to be paroled on February 7, 2025.

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