Chicago (CNN) He is the purported leader of the "AHK Street Gang," a gang in the Chicago area that traffics various narcotics throughout the city region, including heroin and cocaine, according to the Department of Justice.

But Thursday, Jason Brown stepped into a federal courtroom not on drug charges, but for allegedly attempting to provide material support to ISIS.

Specifically, the Department of Justice alleges that on three separate occasions this year, "Brown provided $500 to a confidential source with the intent that the $500 be wired to an individual Brown believed was an ISIS soldier engaged in active combat in Syria." That individual was confidentially working with law enforcement, the DOJ says

The larger question now is: how might have an alleged Chicago area gang leader gotten wrapped up with ISIS?

"One of the notable areas where the Islamic State has been able to recruit"

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