Private Detective Miles Darien is haunted by the escape of crime boss Jonathan Reese whose loan sharking operation had victimized numerous "clients" who were unable to pay off their loans. One of those victims was Miles' friend Olivia Sims.
Miles and the FBI had set up an elaborate sting to bring down Reese's operation. The sting was successful except Reese had evaded the trap Miles and the FBI had set up to capture him.
Months later on another case, the FBI learns that Reese has set up shop in Mexico. Miles jumps at the chance to finally bring Reese to justice. When he and his journalist friend Ryan come up empty in their search, Miles makes a risky and dangerous choice. He asks the local Mexican cartel for help. He explains to them that taking over Reese's operation would be a most fair bounty for helping to locate him. When the cartel finally agrees to assist, they provide an unexpected location, Reese is operating out of a villa in Havana.
The FBI organizes a raid only to find the hideout abandoned. Miles once again makes the risky decision to turn to the cartel. They provide him with a one word update, Chicago.