Driver Caught In Street Takeover Fatally Shot On South Side

CHICAGO — A 20-year-old man was hit by gunfire and killed during an early morning street takeover on Chicago’s South Side. He was identified as Guillermo Caballero Jr., known by family and friends as Memo Jr., was driving his own vehicle when he was fatally shot.

Around 3:17 a.m. Sunday, a mob of vehicles took over the intersection at 59th Street and Western Avenue. Chicago police said that Caballero, Jr. was driving in his black Honda Accord and may have been trapped in the ring of vehicles and pedestrians as he tried to get out of his car. Two participants in the street takeover began shooting toward Caballero’s car, when the young man was struck by gunfire through his windshield.

When officers responded to the scene, 20 to 50 vehicles were speeding away from the intersection as they arrived. A video posted by Chicago Critter on X and shared by CWB Chicago, shows a mob of cars and people fleeing when gunfire erupts.

Illegal street takeovers, also referred to as “sideshows,” are an ongoing issue in the city and suburbs. Cars and trucks swarm an intersection or parking lot. The highly planned, tightly controlled takeovers last just a few minutes, but they intimidate and cause anxiety among the public, who feel powerless to control it. The car mobs are typically organized on social media.

Caballero, Jr., was the oldest of three children. He worked at Foot Locker and had hoped to turn his talent for sales into a career. A GoFundMe has been created to help his family pay for funeral costs.

Chicago police are asking anyone with information, photos or video of the street takeover and homicide, to contact CPD Area One Detectives at 312-747-8380 or by email to Area One Det. Reitz at steven.reitz@chicagopolice.org.

Those with information that could help authorities in their investigation can also leave a tip at CPDtip.com. Tips can be filed anonymously.