Man charged with 3 robberies on CTA trains says he does it ‘because I’m f***ed up’: prosecutors

A Chicago man has been charged with committing three robberies on CTA trains during February and March, including one that grabbed headlines at the Chicago Avenue station on March 1.

Christopher Bennett, 18, told police he does things like train robberies “because I’m f***ed up,” prosecutors said. Judge Barbara Dawkins ordered him held without bail.

Christopher Bennett (right) and a CTA surveillance image of a suspect from the March 1 robbery. | CPD

Bennett and four or five other teens boarded a Red Line train at North-Clybourn along with a man they would soon rob, Assistant State’s Attorney Loukas Kalliantasis said. When the victim pulled out his phone to answer a text, Bennet grabbed the phone and ran while the other group members beat the victim with their fists, causing him to fall to the ground, according to Kalliantasis. He said the group and Bennett exited at the Grand station.

EMS transported the victim to Northwestern Memorial Hospital for treatment.

Police released CTA surveillance images from the Grand station and the train showing three suspects who were wanted for the robbery. A second man was also robbed on the same train and taken to Northwestern for treatment, but Bennett is not charged with that attack.

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, Kalliantasis said. He allegedly took the victim’s phone, credit cards, student ID, keys, and other items, then left the train.

Bennett is also charged with attacking and robbing a man with a handgun at the Central Green Line station on February 26.

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, Kalliantasis said. He tried to pistol-whip the man, then demanded the man’s property while pressing the gun to the victim’s temple, according to the allegations.

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

Chicago police arrested Bennett on Wednesday. He was allegedly wearing the same clothing as the robber from March 1 and March 7. CTA video captured all of the robberies.

Bennett reportedly told detectives that the gun was lighter, not a real firearm. He received a one-year juvenile detention sentence in 2020 for robbery, which corroborates what the robber told the Green Line victim, Kalliantasis said.

During his interview with police, Bennett said he “has no way in life” and “does things like this because he’s f***ed up,” according to Kalliantasis.

Would you please support CWBChicago’s reporting efforts with a contribution or subscription?

About Tim Hecke 256 Articles
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