On his way to California, Tommy decides to stop in Chicago to lay flowers at the grave of his deceased grandmother, only to learn that she is still alive. The revelations keep coming when he meets JP Gibbs, the half-brother he didn't know he had. Thrown for a complete tailspin, Tommy must reevaluate whether to stuff these skeletons back in the closet or put down roots in the Windy City. Never one to shy away from moving weight and making paper, Tommy gets in on a deal involving Vic Flynn and Jenard Sampson. When bullets start flying, Tommy steps in and saves them all. His actions draw the notice of Walter Flynn, Vic’s father and head of the Chicago Irish Mob, as well as Diamond Sampson, Jenard’s brother and a recently released convict and former head of the CBI crew. Tommy is already making waves in the drug game.
When JP’s blues club is shot up, Tommy comes to his brother’s aid and learns that between repairs and his father’s failing health, JP is in dire financial straits. Tommy tells JP he might have a way to help--Tommy approaches Diamond in hopes of forming a lucrative business connection with the gang leader. But their introduction takes a turn when Tommy and Diamond are kidnapped by hitters--Lalo and Peanut--seeking revenge against Diamond for a past crime against their boss. Tommy and Diamond are forced to make dangerous drug drops all over the city. The pressure is compounded when Lalo and Peanut kidnap Jenard as collateral. As Tommy makes the drops, he gets a sense of the Chicago drug landscape and meets potential connections. After Tommy and Diamond successfully complete their mission and get Jenard back, the two men know their paths will cross again.
Tommy sees powder, he sees money. Liliana schools Tommy on the ways of Chicago--unlike New York, Black and White never mix. But Tommy doesn’t believe the rules apply to him. He brokers a sitdown between Diamond --newly reinstated as leader of CBI--and Walter Flynn in an attempt to get Chicago’s two biggest drug crews to work together. But Walter’s toxic racism makes any possibility of cooperation impossible. Hearing about the waves Tommy is making, CLAUDIA FLYNN rolls up on Tommy to size him up for herself. But Tommy can read Claudia like an open book. Tommy turns from business to pleasure when GLORIA hits him up, not realizing that Gloria is Vic’s old flame for whom he still holds a candle.
Tommy apologizes to Diamond for how things went down with Walter--he didn’t know Walter’s heart was filled with such hatred. Similarly, Vic comes to Tommy and Diamond, hat in hand--he doesn’t share his father’s views and wants to work altogether. Meanwhile, Liliana finds herself at the mercy of Serbian gang members--her stash of coke belongs to them. Tommy saves Liliana, but they both know more Serbs are soon to follow, including TATIANA, the Serbian who spared Tommy’s life in POWER. Tommy asks for Diamond and Vic’s support, but Diamond declines. He’s not willing to cross a vicious crew like the Serbs. But with Vic’s help, Tommy manages to take down Tatiana and her men. But while this battle has been won, Tommy knows the war against the Serbs is just beginning.
Claudia introduces Tommy to her new designer drug: DAHLIA. The high is unlike anything Tommy has ever experienced. He brings a sample to Liliana; she discovers it’s impossible to cut. He and Claudia strike a deal--if he can eliminate a problem for her, they’ll partner up on this operation with Tommy running point. Meanwhile,the leader of the Serbian Crew --RODOVAN MIRKOVIC--arrives in Chicago to exact revenge and get his drugs back. Tommy knows he has to hit them first so he brings Diamond, Vic, Jenard, and other FLYNN and CBI SOLDIERS together to form an army. Their attack against the Serbs doesn’t come without costs--Vic and Jenard’s respective lieutenants --SIMON and ELIJAH--are killed in the crossfire. Liliana is kidnapped by Mirkovic and Tommy must rush to save her--giving Mirkovic his drugs back in exchange for Liliana.
Tommy and Claudia work together to recruit distro for Dahlia,setting up locker drops at the Chicago Convention Center. Claudia chafes at the plan, thinking it's too low-rent for a high-end drug like Dahlia. But Tommy pushes back--Claudia is new to this game, she needs to listen to him and play by his rules. Thinking she knows better, Claudia doesn’t follow Tommy’s guidance and almost pays the price when Reggie comes after her and she’s forced to kill him. Vic and Gloria reconnect but their happiness is short-lived when the Serbs make an attempt on Vic’s life. Vic and Gloria both survive, but Walter is furious. He takes matters into his own hands, killing a room full of Serbs in retribution, not knowing that he’s fanned the flames of a full-blown gang war.
Joseph Sikora
Tommy Egan
Kris D. Lofton
Jenard Sampson
Anthony Fleming
JP Gibbs
Isaac Keys
Diamond
Lili Simmons
Claudia Flynn