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Lil Zay Osama is back in federal custody, and this time, the stakes are much higher.
The Chicago rapper, born Isaiah Dukes, is one of six men charged in connection to a violent home invasion in Winnetka, Illinois, where prosecutors say the suspects posed as a food delivery to gain entry before storming the house at gunpoint.
According to federal authorities, the March 8 incident turned into an hour-long hostage situation. The suspects allegedly forced their way inside with loaded weapons, physically restrained the victims, and demanded access to a safe, personal computers, and cryptocurrency accounts.
Prosecutors claim one of the men called Lil Zay Osama during the robbery for instructions on how to access the victim’s crypto.
Dukes was arrested on April 10 and charged with conspiracy to commit robbery and kidnapping. All six defendants pleaded not guilty and are being held without bond as they await trial.
If convicted, the kidnapping conspiracy charge could carry a life sentence, while the robbery conspiracy charge brings up to 20 years behind bars.
His attorney is pushing back hard, saying the rapper was not at the scene and did not orchestrate the crime.
This latest case adds to Zay’s legal troubles after he previously served federal time in 2024 for possessing an illegal machine gun that was left in a rideshare vehicle.










