Chicago — A 30‑year‑old Uber driver from Cicero still can’t shake the memory of what happened after a late‑night shift in Kenwood. Police allege that on the morning of July 19, 2025, an 18‑year‑old man named Jroy Ramey used a gay dating app to lure the driver to a quiet alley on South Drexel Boulevard. Once there, what the victim thought was a routine meet‑up turned into a nightmare he won’t forget.
Around 1 a.m., the driver was chatting with someone on the hookup app while waiting for rides. Believing he was heading into a harmless meet‑up, he parked and followed directions given to him through the app. That’s when things turned dark. Investigators say Ramey and a companion approached him, walked him to a secluded spot and pulled off what prosecutors describe as a calculated ambush.
According to charging documents, Ramey appeared holding a bat‑like object and demanded the driver’s phone. When the driver hesitated, the second suspect allegedly pressed a gun against his leg and back, threatening to shoot him unless he complied. The robbers forced the driver to unlock his phone using facial recognition, then took his Apple Watch before ordering him to keep his head down as they fled.
The victim managed to drive to the nearest police station and report what had happened. In the days after the attack, he discovered that someone had accessed his banking information on the stolen phone and spent at least $1,856 on unauthorized transactions. Investigators say they also found food orders placed through his Uber Eats account, including at least one delivery sent to Ramey’s home address.
Police executed a search warrant at Ramey’s home later that week in connection with a separate investigation. Officers reportedly recovered a loaded handgun with a 30‑round magazine and multiple driver’s licenses, identification cards, and bank cards belonging to people who did not live at the residence. Cell‑phone data also allegedly placed Ramey at the scene of the Drexel Boulevard robbery.
Ramey eventually turned himself in to face charges in this incident and in a separate armed robbery from earlier in 2025. The Uber driver later identified him in a photo lineup. A judge has ordered Ramey detained as he awaits trial on armed robbery charges carrying a dangerous weapon.
The case has raised concerns among local drivers and police about the risks of meeting strangers through dating apps while on the job. Authorities remind rideshare workers and users alike to stay vigilant and avoid isolated encounters late at night.
