Chuckyy is in major legal trouble. The OTF-affiliated rapper was recently arrested in Chicago.
According to a Cook County Sheriff’s Office arrest record obtained by XXL, Chuckyy was arrested in Chicago on Tuesday (June 23). The 20-year-old rapper, born Charles Edward Davis, is currently being held in a Cook County jail with no bond. Details surrounding his arrest remain undisclosed. His next court date is scheduled for June 29.
XXL has reached out to Chuckyy’s rep and the Cook County Sheriff’s Office for comment.
Chuckyy is connected to Lil Durk’s Only The Family imprint, a partnership that kicked off in 2024 following Durkio securing his first Grammy win for Best Melodic Rap Performance on the J. Cole-assisted hit “All My Life.”
Since then, Chuckyy has become the Windy City’s rising drill rap star with streaming hits like “My World,” “Me vs. Me,” “Kobe,” “Free Smurk OFNG,” and others. Lil Durk’s arrest in October of 2024 for an alleged murder-for-hire plot hasn’t slowed Chuckyy down; he’s keeping his foot on the gas. The young rapper dropped his Bloodbathh Vol. 2: Violate We Demonstrate project last year and recently debuted a visual for his latest single, “Lamb Chop.”
In an interview with XXL back in February, Chuckyy reflected on his mentor’s legal predicament, noting that Durk’s career advice still continues to guide his path.
“A lot of this sh*t that he said a while ago still help me now,” he said. “He the reason that I probably ain’t broke right now. He was the one that was in my ear telling me…’Don’t buy that. Don’t do this.’ Or if I do buy it, he’ll come reimburse me. He ain’t even got to do no sh*t like that. We both grown. So, I f**k with bro. Free bro. That sh*t gonna work out.”
Brothers gonna work it out.
