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.

Tommy makes bold moves to connect CBI directly with the cartel as he hustles to stay ahead of the many adversaries out for his blood. Diamond is forced to make a decision that has dire consequences.

Tommy and Diamond suspect a snitch and put their inner circle to the test. Mireya gives Tommy a key piece of information. The war between Miguel and Mirkovic comes to a head.

Tommy orchestrates the grand finale of his long game to take over Chicago’s drug world. When he is faced with devastating personal sacrifices, he finds that he might just lose more than he ever stood to gain.