Boyhood pal of Chicago drill rapper Lil Zay Osama snitched about Winnetka home invasion, feds say

A childhood friend of rapper Lil Zay Osama and alleged member of a robbery crew cooperated with federal authorities, telling them he recognized the rapper’s voice and nickname as they were on the way to the north suburban Winnetka home invasion that “didn’t go as planned,” according to federal authorities.

Meanwhile, charges were announced for a seventh person in the March 8 attack: Tyrese Fenton-Watson, 23, of Chicago, was arrested April 28 and faces robbery and kidnapping charges in the home invasion, according to U.S. Attorney Andrew Boutros’ office.

The person who cooperated “admitted to hearing a conversation about the robbery between Osama and Jalen Chambers,” his cameraman, while on their way to the home, according to federal prosecutors. He was arrested March 20.

After getting inside, the crew member who cooperated told authorities he grew up with Osama, recognized his voice and could hear Chambers saying the name “Zay,” a name Osama goes by, over the phone, prosecutors said.

The 28-year-old Osama, whose real name is Isaiah Dukes, is among six others facing the same charges. Three other Chicago men were also charged. They are Dashun Brown, 24; David Franklin, 24; and Anthony Ramsey, 22. Also facing charges are Khiell Dukes, 30, of Elgin; and Chambers, 24, of Bourbonnais.

Prosecutors say Brown posed as a food delivery driver, prompting someone inside the Winnetka home to open the front door. That’s when Brown, Franklin and Chambers allegedly forced their way inside, armed with loaded firearms. The feds say two unidentified co-conspirators joined them.

The intruders allegedly held the victim captive for about an hour and “used firearms to physically restrain the victim,” prosecutors said. They also allegedly demanded access to a safe, computer and online accounts at gunpoint.

Eventually, the intruders fled the home and met up with Osama, Dukes, Ramsey and others — who conducted a search to make sure all of the robbery proceeds were collected, according to prosecutors.

New details were released by federal prosecutors, including that Osama and the others were in the area at the time of the robbery and were seen at an Elgin hotel hours earlier, according to text messages, surveillance video and phone location tracking.

Additionally, three Rolex watches and a laptop belonging to a victim who wasn’t home at the time of the invasion were all taken from that person, who owns a cryptocurrency business based outside of Illinois but works out of Winnetka, according to a criminal complaint.

Also key to the investigation was surveillance footage that captured a black Acura RDX with black rims, dirt on the sides and rear, a blue sticker in the bottom of the driver’s side windshield and no license plate pull into and leave the driveway of the home. Three days later the Acura — which was reported stolen — was found in the 600 block of West Garfield Boulevard in Chicago’s Back of the Yards neighborhood.

Osama and Ramsey were angry with the other intruders because the robbery didn’t go as planned, according to the crew member, prosecutors said.

Those six charged earlier with the home invasion have all pleaded not guilty and were ordered to remain in federal custody without bond. Kidnapping conspiracy is punishable by a maximum sentence of life in federal prison, while robbery conspiracy is punishable by up to 20 years.

The rapper’s defense attorney, Michael Clancy, said Osama “is hoping to get to trial as soon as possible.”

“My client was not present at the robbery, and he did not set up this robbery,” Clancy said.

Osama has faced federal trouble before. A federal judge in Brooklyn sentenced him in 2024 to 14 months in prison after he pleaded guilty to possession of a machine gun.

Contributing: Jon Seidel

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