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.

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 former foe turned friend is at the mercy of a notorious criminal organization who resurface to reclaim what's theirs. The group is led by an enemy from Tommy's life back in New York who is still out for blood.

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 crew can barely keep up with the demand and they need more help to increase their supply. More shocking details about Tommy's family surface, and he realizes the news could potentially affect his business.