A masked gunman dressed head to toe in black robbed three separate lawn care workers at gunpoint across Englewood within a 20-minute span, demanding their cell phones and wallets before fleeing in a car. Chicago police warned the public about the string of robberies targeting outdoor workers on the South Side, with no injuries reported in any of the incidents.
According to the Chicago Sun-Times, the first robbery happened at about 9:30 a.m. on September 28 in the 5900 block of South Parnell Avenue, police said. Minutes later, at 9:47 a.m., the gunman struck again in the 5500 block of South Union Avenue, and by 9:50 a.m. he had hit a third worker in the 5500 block of South Ashland Avenue, police said. Each time, the masked suspect approached lawn care workers while they were on the job, demanded their phones and wallets, and then fled by car.
A Pattern of Targeting Outdoor Workers
The rapid-fire nature of the spree, with three stickups inside 20 minutes across a handful of blocks, points to a mobile offender moving quickly between job sites before police could respond. Outdoor service crews have been targeted this way before in the Chicago area; a 2017 case saw two gunmen rob a landscaping crew at gunpoint in Calumet City, making off with cash, watches, and personal belongings, as reported by CWBChicago. Outdoor crews often carry cash and electronics while working in full public view, making them an easy target for someone looking for a fast grab-and-run.
The spree unfolded in the 7th Police District, which covers Englewood and has routinely ranked among the city's most violence-impacted districts. CWBChicago's analysis of police staffing and crime data found the district recorded 141 shooting victims in 2025 alone. Englewood itself, designated Community Area 68 on the city's South Side, spans roughly 3 square miles and had an estimated population of 23,195 in 2024, with Black residents making up about 86% of that population, according to Wikipedia.
Detectives Investigating, Asking Public for Tips
Area 1 Detectives, who handle felony and violent crime cases across South Side districts including the 7th District, are investigating the robberies. Anyone with information is asked to call detectives at 312-747-8380. Chicago police's standard community safety guidance for armed robbery sprees urges victims and witnesses never to resist or chase fleeing suspects, to try to remember distinct physical traits of the offender, and to preserve any surveillance video immediately for detectives.
The Englewood robberies weren't the only daytime armed crime activity reported on the South Side that day. Chicago police also issued separate warnings on September 28 about dozens of car burglaries across the Near South Side and South Commons, where armed suspects threatened vehicle owners, according to CBS News Chicago. The overlapping alerts underscore how stretched South Side patrol and detective resources can be on any given day.
Citywide Robbery Trends Shape Police Strategy
The Englewood spree also fits into a broader pattern city officials have been grappling with for several years. Back in April 2024, Chicago Police Superintendent Larry Snelling and Mayor Brandon Johnson announced a focused department strategy aimed at curbing persistent robbery sprees after the city recorded more than 11,000 robberies in 2023, a 23% jump over the prior year driven largely by armed, mobile crews, per WTTW News. That strategy leaned heavily on video tracking and license-plate readers to chase down fast-moving crews like the one that hit Englewood lawn care workers on September 28, though no arrests had been announced as of this report.
