OTF Rapper Chuckyy Arrested in Chicago, Held Without Bond

In a reminder that Chicago‘s drill scene and its legal headlines remain tightly braided, 20-year-old Chuckyy has been taken into custody on alleged weapons possession charges. The arrest was logged in Cook County on Tuesday, June 23, according to a Cook County Sheriff\’s Office record obtained by XXL.

Arrest and status

Born Charles Edward Davis, the OTF-affiliated rapper is currently being held in a Cook County jail with no bond. Details about the stop or the evidence against him have not been made public; his next court date is set for June 29. XXL has reached out to Chuckyy\’s representation and the Cook County Sheriff\’s Office for comment.

Where this sits in his career

Chuckyy emerged as one of the Windy City\’s rising drill acts after linking with Lil Durk\’s Only The Family imprint, a partnership that began in 2024 following Durk\’s first Grammy win for Best Melodic Rap Performance on the J. Cole-assisted “All My Life.” Streaming tracks such as “My World,” “Me vs. Me,” “Kobe,” and “Free Smurk OFNG” helped build his profile, and he released Bloodbathh Vol. 2: Violate We Demonstrate last year. He also recently premiered a visual for his single “Lamb Chop.”

Lil Durk\’s own legal troubles following his October 2024 arrest on an alleged murder-for-hire plot have been part of the backdrop for the OTF roster, but Chuckyy has continued to put out music and maintain momentum.

Speaking to influence

When XXL interviewed Chuckyy in February, he spoke plainly about the practical mentorship Durk has provided — less mythmaking, more day-to-day counsel on surviving the industry and the streets.

“A lot of this sh*t that he said a while ago still help me now,” Chuckyy told XXL. “He the reason that I probably ain\’t broke right now. He was the one that was in my ear telling me