A 41-year-old man widely known in Chicago drill circles as “The Oldest YN” was reportedly killed early Wednesday morning in a shooting outside a 7-Eleven in the Loop, according to social media reports that spread rapidly across hip-hop accounts. Police have confirmed a fatal double shooting near State and Lake streets but have not released the name of the deceased victim.
Officers responded around 2:30 a.m. on Oct. 28 and found two men suffering gunshot wounds near the convenience store, close to the Chicago Theatre. One man was pronounced dead at Northwestern Memorial Hospital after being shot multiple times. A 38-year-old man was wounded in the right leg and listed in fair condition. Witnesses told police a vehicle pulled up and gunfire erupted on the sidewalk. Area 3 detectives are investigating; no arrests have been announced.
Major local outlets including the Chicago Sun-Times, ABC7 Chicago, NBC Chicago, and the Chicago Tribune have covered the shooting but stopped short of identifying the man who died. Identification of the victim as “The Oldest YN,” also referred to as OYN, has so far come exclusively from social media accounts such as Daily Loud, My Mixtapez, and SayCheese. Those posts describe him as a member of the TYMB set from the Woodlawn area who had gained attention for continuing to identify with the “YN” label well into his forties.
In interviews that circulated earlier this year, including appearances on platforms such as DJUTV, the man claimed the “Oldest YN” moniker and spoke about growing up in the Robert Taylor Homes, later ties to the 65th & Maryland area, and the history of TYMB—a long-running Black Disciple-associated block. He framed age as irrelevant to the culture he participated in, a stance that set him apart from many of his peers who had moved into “big bro” or elder roles. Some accounts online have claimed he had six children and had been involved in publicized tensions with members of the Bloodhounds set; none of those details have been independently verified by news organizations.
The shooting is the second double shooting in the Loop in three days. On Monday night, a gunman entered a different 7-Eleven on East Adams Street, struggled with a 26-year-old man, and opened fire. The 26-year-old was hit multiple times and a 23-year-old bystander was grazed; both survived and were in fair condition. Police have treated the two incidents as separate.
For observers of Chicago drill, the reported death of “The Oldest YN” lands against a backdrop of repeated losses among the generation that shaped the sound. Figures who built followings through street interviews, vlogs, and online presence have become as visible as the music itself in a scene defined by rapid turnover. Until Chicago police or the medical examiner’s office release an official identification, the connection between the man found outside the State and Lake 7-Eleven and the internet personality known as “The Oldest YN” remains based on community reports rather than confirmed public records.
The investigation is ongoing.
