He’s going to back to prison for robbing Boystown Walgreens *again*


Raymond Bensfield (inset) has been sent to prison for robbing the Walgreens at 3201 North Broadway. Again. | CPD; Google

Raymond Bensfield, who was charged with robbing stores in Lakeview and Lincoln Park last year while he was on parole for robbing stores in Lakeview and Lincoln Park in 2018 while he was on parole for robbing stores in Lincoln Park in 2016, is going back to prison.

Bensfield this week pleaded guilty to two counts of aggravated robbery and received a pair of concurrent six-year prison sentences from Judge Shelley Sutker-Dermer. He’ll receive credit for 422 days that he spent in jail before sentencing.

On September 19, 2019, Bensfield brandished a knife and robbed a store in the 2700 block of North Clark. Three days later, he allegedly threatened to shoot an employee to tried to stop him from stealing a case of beer from Walgreens, 3201 North Broadway.

Those two robberies took place about three months after Bensfield got out of prison for robbing the same Walgreens in 2018. He received a three-year sentence but only served half of the time, according to state records.

The 2018 Walgreens robbery took place five days after he got out of prison for robbing 7-Eleven, 2619 North Clark, and Walgreens at 2817 North North Clark in 2016. He received four years for those hold-ups but, again, served only half of the time.

Besides the crimes that he went to prison for, Bensfield is infamous for stirring up trouble at retailers along Clark, Broadway, and Diversey. Store employees have accused him of punching them in the face, brandishing knives, and threatening to shoot them.

His next parole date has not been set. But, with time served and a standard 50% sentence reduction for good behavior, he will likely be in prison for a little under two years. Mark your calendars, retailers.

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