Second man sentenced in series of Grindr hook-up robberies

Stephen Jackson (left) and Trenell Kirkman | CPD

A second man who used the Grindr gay dating app to lure men into a series of robberies on the North Side has been sentenced to 18 years in prison.

Stephen Jackson, 26, pleaded guilty to three counts of armed robbery and one count of attempted armed robbery in a plea deal with prosecutors. His accomplice, Trenell Kirkman, received an 18-year sentence late last year.

A total of 9 men told police that a pair of offenders lured them into armed robbery ambushes in Rogers Park during the fall of 2017. Chicago police arrested Jackson and Kirkman after an undercover officer arranged to meet with them in a sting operation, prosecutors said.

Jackson received four concurrent prison sentences in exchange for his guilty plea: three 18-year terms for three of the robberies and a 15-year term for an attempted robbery with a firearm, according to state records. He is scheduled to be paroled in October 2026 after serving nine years. Illinois gives most prison inmates a 50% sentence reduction for good behavior.

Prosecutors dropped multiple felony counts of aggravated kidnapping and aggravated unlawful restraint as part of their agreement with Jackson.

Judge Earl Hoffenberg oversaw the case.

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CWBChicago was created in 2013 by five residents of Wrigleyville and Boystown who had grown disheartened with inaccurate information that was being provided at local Community Policing (CAPS) meetings. Our coverage area has expanded since then to cover Lincoln Park, River North, The Loop, Uptown, and other North Side Areas. But our mission remains unchanged: To provide original public safety reporting with better context and greater detail than mainstream media outlets. Our editorial email address is