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 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.

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.

Tommy and Diamond continue gaining territory behind Miguel’s back, but Diamond is pulled in other directions. Jenard gets more than he bargained for. Tommy puts Vic’s loyalty to the test.