On the night of January 18, 2026, the West Pullman neighborhood on Chicago’s far South Side became the scene of a targeted fatal shooting that claimed the life of 37-year-old Troy Hollingsworth.
Around 9:30 p.m., Hollingsworth was seated inside his Nissan Maxima in the 100 block of East 118th Place, a residential street lined with homes in this working-class community. Without warning, an unknown individual approached the vehicle and opened fire, unleashing multiple rounds that struck Hollingsworth several times.
The sudden gunfire shattered the evening quiet, prompting immediate 911 calls from nearby residents who heard the shots. Chicago Police Department officers from the 5th District responded swiftly to the location, arriving to find Hollingsworth unresponsive in the driver’s seat with severe gunshot wounds. Despite efforts by first responders to render aid at the scene, he was pronounced dead on site, marking another addition to the city’s ongoing toll of gun violence.
Investigators quickly classified the incident as a targeted attack rather than random, given that the offender approached on foot specifically toward Hollingsworth’s vehicle before fleeing the area. No arrests have been made in the early stages of the probe, and detectives are actively reviewing potential surveillance footage from the block, canvassing for witnesses, and pursuing leads into possible motives.
Troy Hollingsworth was well-known in Chicago creative circles as a talented photographer and the owner of PolaBear Red Filmz, a production company focused on videography and visual storytelling. His work captured community events, personal milestones, and the vibrancy of local life, earning him respect among peers and clients.
Beyond his professional pursuits, Hollingsworth shared a notable family connection as the brother of Adam Hollingsworth, better known as the “Dreadhead Cowboy,” a prominent Chicago activist and influencer recognized for his advocacy on behalf of children and against violence.
With no public details yet on funeral arrangements or further family statements, the focus remains on supporting loved ones while authorities work to bring accountability. This incident underscores the persistent challenges of street violence in neighborhoods like West Pullman, leaving residents once again mourning a life cut short under tragic circumstances.