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 aide. Determined to lend a helping hand, Tommy approaches a local dealer proposing 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 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 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.

Tommy's new product is spreading like wildfire across Chicago. The current success isn't good enough for Tommy. He wants to own the entire city and is determined to figure out how to do so, no matter the cost.

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.

Vic faces a devastating loss. Walter is ready to go to war and sends for heavy hitters. Tommy soon realizes he needs more power but is turned down by one of his closest allies and is forced to turn to an unlikely resource.

Decisions are made by those closest to Tommy which could leave him powerless. When the gangs face off, truths come to light, shifting the power of the drug game. This battle may be over, but the war is far from won.

Tommy and Diamond hustle to keep CBI's game ahead of Jenard's new faction in the streets, while Tommy makes solo moves to avenge Liliana's death. All the while, Tommy hasn't forgotten his ultimate goal to become a kingpin.

Jenard’s crew seeks revenge as Tommy learns of a rivalry between Miguel and the Serbs that he and Diamond leverage to CBI’s advantage. Meanwhile, the Feds pursue a task force with Tommy at the center of the investigation.

Tommy and Diamond expand their business to prisons, the Feds put together a task force to take down CBI, and Jenard struggles to maintain control. Tommy faces off with Walter and gets closer to avenging Liliana's death.

Tommy and Diamond keep dangerous secrets from each other, Jenard clashes with his crew, and Vic teams up with Claudia one last time. D-Mac ends up entangled deeper in the drug game than he ever intended.

Heightened police presence threatens Tommy and Diamond's bottom line and they form a coalition with a rival gang. Jenard hits rock bottom, and the Flynn family loyalties are tested with devastating results.

Tommy and Diamond expand their coalition by bringing Vic and Jenard into CBI. Mirković warns Tommy against encroaching on Serb territory, and makes good on his threat with catastrophic results.