On his journey to LA, Tommy stops in Chicago, only to discover shocking news about his family. Tommy must decide whether he is going to force his skeletons back in the closet, or put down roots in the Windy City.

When JP receives an unexpected warning, Tommy comes to his aid; determined to lend a helping hand, Tommy approaches a local dealer to propose a business arrangement, but their introduction takes a turn for the worse.

Tommy finds himself face-to-face with a ghost from his past; the reunion unearths a discovery when Tommy stumbles across hidden product; Tommy brokers a sit-down between rivals and learns the true nature of the feud.

Tommy's new friend remains at the mercy of a resurgent and notorious criminal organisation, led by a bloodthirsty old enemy from Tommy's New York days.

Tommy is offered a profitable solution, from an unlikely source, that may be the answer to his troubles. Intrigued, Tommy is informed he must first address a problem threatening the new venture before it begins.

Tommy and his new business partner recruit soldiers to take over the drug game in Chicago. Tommy finds a lucrative location for distribution that doesn't fit with his partner's vision for a more upscale clientele.