Serial criminal who once stole a dead man’s wallet has robbed another CTA passenger, police say

CHICAGO — In the (almost) eleven years since CWBChicago was created, Derrick Robie may be the person we’ve published the most stories about. So, you’ll probably not be surprised when we tell you that Robie is sitting in the Cook County jail today because one of our readers helped identify him by name as the person who recently pepper sprayed and robbed a man at the Granville Red Line station.

The first story we published about him was about a “nice” Florida man who declined to pursue felony charges after identifying Robie as the man who held a knife to his stomach and demanded his phone in Boystown in June 2017.

“Gimme the phone, you know what this is,” Robie allegedly told the tourist at knifepoint.

The very next week, a 60-year-old homeless man wasn’t as “nice.” He pressed charges after Robie knocked his change cup from his hand and stole his money in Boystown.

But the most sickening Derick Robie story came along in January 2018. That’s when he and an accomplice stole a wallet from the pocket of a 49-year-old man who was lying dead or dying after falling down the stairs at the Loyola Red Line station. Five days later, before cops figured out that he was involved in stealing the fallen man’s property, Robie robbed a CTA passenger at the Morse Red Line station.

Shortly after he got out of prison, in May 2020, Robie and three other people tried to rob an off-duty Chicago cop outside the Town Hall (19th) District station in Lakeview. He got 3½ years for that, got paroled, and got arrested again within three months for robbing yet another passenger at the Morse Red Line station.

After the victim refused to give him money, Robie asked if he wanted to see his gun, prosecutors said. The man handed over $10.

“See that’s all you had to do,” Robie allegedly replied. “It didn’t have to come to this.”

He pleaded guilty to unlawful restraint in that case, receiving a 2½-year sentence last March. State records show he was released from prison in July.

Kinda scary for regular citizens

Earlier this month, Chicago police released a CTA surveillance image of a man who had recently pepper sprayed and robbed a 23-year-old man on the Granville Red Line platform.

Derrick Robie and a CTA surveillance image of the robbery suspect (Cook County sheriff’s office, Chicago Police Department)

It didn’t take long for a reader to recognize him.

“The person in the image is Derrick Robie,” their email to CWBChicago began. “The same guy who tried to rob an undercover cop, the same guy who stole a wallet from a dead man…. Now he [carries] a gun most times, and often he hangs out just east of the Red Line train. It’s kinda scary for regular citizens who see him often.”

We passed along the reader’s suspicions to CPD on February 6. They put his picture in a photo line-up the next day, and the Granville robbery victim pegged Robie as the person who, along with an accomplice, sprayed and robbed him, according to a police report.

Chicago cops arrested Robie when they recognized him at the State-Lake Red Line station around 1 a.m. Wednesday.

Judge David Kelly detained him as a public safety threat this week. The Illinois Department of Corrections is also reconsidering his parole status.

Robie’s alleged accomplice was detained in the case just hours before cops located Robie in the Loop.

John Wesley, 24, has been arrested and released six other times since Illinois eliminated cash bail on September 18, according to Chicago police records.

The two men are now facing prison time for allegedly taking a total of $20 cash from the victim.

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About Tim Hecke 252 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