As things heat up in Chicago, there’s a ton of shooting and a few lost bodies. One thing about Tommy, he’s going to bring the action! And episode five is full of action — arguing, slapping, a robbery, a kidnapping, and more.
Tommy’s been on edge since killing Tatiana. He knows that he’s now at war with the Serbs. Claudia runs up on him, and he’s skeptical about her motives. She tells him about her designer drug, but Tommy immediately calls her bluff — the young Flynn doesn’t have anyone to move her product. A quick thinker and solid businesswoman, Claudia puts her money where her mouth is and passionately kisses Tommy, which allows him to sample her product. And her sales pitch works. Tommy has the best high of his life, “no hard crash, no cottonmouth, no aftershocks at all.”
Back at his apartment, he can’t stop talking about the experience to Liliana. He asks her to figure out the chemical composition of the drug. But the task is damn near impossible. Liliana tells him the drug is unable to bond to any other substance and basically self-destructs. While trying to solve this mystery drug, Lilianna proposes a partnership with Tommy. He resists at first but eventually realizes that their history makes them a good team. Plus, the drug game is all either of them knows. And more importantly, she has no family. And just like that, they officially become partners who function more like sister and brother.
On the other side of Chicago, while out for a run, Diamond runs into the crooked cop. He forces him to get in the car without any explanation. Diamond asks the cop about his vendetta against him and learns that the bad batch of drugs he once sold affected a girl named Keke Watkins, who was close to the cop. While the officer tries to guilt-trip Diamond, the CBI leader gives him a dose of his own medicine and questions him about his crooked ways, i.e., being on Vic’s payroll. This throws the cop off (well-played Diamond), and he lets Diamond out of his car.
Jenard is still on his high horse, but his anger gets redirected toward Tommy. He’s been watching his brother make major moves with Tommy and feels left out. Elijah suggests that the two of them start their own shit, but Jenard reminds him that CBI is much of his as it is Diamond’s.
Apparently, everyone wants Tommy dead! The Serbs have a problem: Tatiana is dead, and it is because of Tommy Eagan. So they put a bounty on Tommy’s head.
The Serbs aren’t the only organization in the Chi with a problem. As Claudia attempts to build her organization, the tension between her and Mai increases. Mai isn’t satisfied with Claudia’s drug dealing abilities — the product isn’t out on the streets yet because of the distribution challenges. She threatens to go elsewhere.
Meanwhile, the three amigos (Tommy, Vic, and Diamond) find their way back to each other. Tommy needs more manpower to take down the Serbs, and with the Serbs forced out of Chicago, it opens up the entire west side, an area that Vic nor Diamond ever had access to. The three men put together a plan to attack the Serbs and share an equal stake in their pipeline. As business partners, they will run all votes equally. Before wrapping up the terms, Tommy makes a specific request to put Jenard back in the mix. He’s well aware of how Jenard feels about him and doesn’t want any trouble.
When Diamond presents the plan to Jenard, he’s hesitant but eventually agrees.
Now that his plans to take down the Serbs are in place, Tommy circles back to Claudia and agrees to be her distribution. They go back and forth about the financial terms of their relationship and land on 60% for Tommy and 40% for Claudia. With a new distro and a pissed-off partner, Claudia has Tommy steal the drums of Dahlia from right under Mai’s nose. When Mai realizes the product is gone, Claudia uses the moment to convince Mai she needs her, but things go left. Mai lashes out at Claudia and even slaps her. Before she can make it out of the luxury penthouse, Claudia stabs her in the back with an ice pick.
Before heading out to move with his new partners, Victor surprises Gloria with the land he purchased. The two share an intimate loving moment and dream about their future together— a house with a wrap-around porch, a white picket fence, and kids. But the dream is short-lived as Walter finds out about their relationship. He then visits Gloria and threatens her. Although she owes the Flynn family money, Walter’s racism runs so deep that he offers Gloria a cleared debt if she leaves his son alone.
When Vic discovers his father’s helicopter behavior, he confronts him. Serious about his son marrying an Irish girl and giving him Irish grandchildren, he slaps Vic during their argument. In an attempt to mend the relationship between her brother and father, Claudia decides to visit Gloria herself. She presents her with a monetary offer she hopes Glo can’t deny, but it doesn’t work.
So much happens at once in Chicago. While Claudia was murdering Mai and bribing Gloria, Lilianna’s hard-headed ass sampled the designer drug and left the house high. She ends up getting kidnapped AGAIN!
And while the Serbs successfully capture Lilianna, the three amigos run up on two different groups of Serbian men, quickly eliminating them before they can retaliate. And per usual, the shootout scene is epic! There are guns blazing and bodies dropping every other second. However, there are also some major losses on Vic and Jenard’s end. Sonny and Elijah are killed by Serbian men. After the trio realizes they’ve killed all of the Serbs, through a phone call to Tommy’s phone, they find out that Liliana has been captured. But Tommy is left on his own to save her. Vic and Diamond let him know they held up their end of the bargain. All Tommy can do is respect that.
On his own, he goes to meet with the Serbs to rescue Liliana. In the middle of debating who caused more harm to who and who should kill who, a black truck swerves around the corner firing bullets. The commotion distracts the Serbs and Liliana gets away. Almost immediately, she and Tommy realize that she’s been shot. Luckily the bullet pierced right through her arm. We soon find out that it was Jenard behind the mask. His motives are unclear. Was he attempting to get revenge against the Serbs for Elijah? Was he trying to make sure Tommy died? We will have to wait and see.