S1, E2: 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.