14 year sentence for man who committed 3 CTA robberies ‘because I’m f***ed up’

A Chicago man who told police he participated in a string of violent robberies aboard CTA trains because “I’m f***ed up” was handed a 14-year sentence this week.

Christopher Bennett, 19, pleaded guilty to two counts of armed robbery, one count of robbery, and one count of aggravated battery of a transit employee, according to clerk of court records. Judge Michael Clancy sentenced him to concurrent terms of 14 years for the armed robberies, three years for the robbery, and two years for the aggravated battery.

The first robbery occurred around 9 p.m. on February 26, 2022, at the Central Green Line station. Prosecutors said the victim was preparing to exit the train when Bennett grabbed the overhead train bars, lifted himself up, and kicked the man with both feet.

Officials said he tried to pistol-whip the man, then demanded the man’s property while pressing the gun to the victim’s temple.

Bennett went through the man’s pockets, took two phones and some money, then left the train. The victim followed him and tried to regain his property, but Bennett pressed a gun to the man’s stomach and told him not to follow.

Prosecutors said Bennett told the man that he recently got out of jail on a juvenile case and agreed to return one of the victim’s phones, but he kept the other phone and cash.

Clancy handed him 14 years for that crime.

Bennett received three years for a robbery three days later at the North-Clybourn station. Prosecutors said he and four or five other teens boarded a train with a man they would soon rob.

When the victim pulled out his phone to answer a text, Bennet grabbed the device and ran while his accomplices beat the victim with their fists, causing him to fall to the ground.

A second man was robbed on the same train and taken to Northwestern Memorial Hospital for treatment, but Bennett was not charged with that attack.

Police later released CTA surveillance images showing three suspects who were wanted for the robbery.

Christopher Bennett (right) and a CTA surveillance image of a suspect from the March 1, 2022, robbery. | Chicago Police Department

Then, around 8 p.m. on March 7, a man was looking at his phone on a Red Line train near Harrison when Bennett allegedly entered from an adjoining car. Wearing the same clothing he wore on March 1, Bennett pressed a gun to the victim’s throat and demanded his wallet, prosecutors said. He allegedly took the victim’s phone, credit cards, student ID, keys, and other items, then left the train.

That crime earned him another 14 years.

Finally, Clancy sentenced Bennett to two years for battering another Red Line passenger on a train at 35th on March 15, 2022.

Chicago police officers spotted Bennet at the Cermak-Chinatown station the next day and took him into custody.

During an interview with investigators, Bennett said he “has no way in life” and “does things like this because he’s f***ed up,” prosecutors alleged.

His effective 14-year prison term will be reduced by 50% for good behavior. He also earned 582 days of credit for time spent in jail since being arrested, 438 credit days for participating in the jail’s education programming, and seven days of credit earned in an employment program, according to court records.

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Tim Hecke is CWBChicago's managing partner. He started his career at KMOX, the legendary news radio station in St. Louis. From there, he moved on to work at stations in Minneapolis, Chicago, and New York City. Tim went on to build syndicated radio news and content services that served every one of America's 100 largest radio markets. He became CWBChicago's managing partner in 2019. His email address is tim@cwbchicago.com