In the early stages, the film delves into the infamous life of James 'Whitey' Bulger, a feared South Boston crime lord whose violent reign spanned several decades. His notorious criminal activities ranged from drug trafficking to murder, all while he maintained a facade of being a community benefactor. The documentary highlights Bulger's manipulative prowess and explores his complex relationship with the FBI. This relationship was marked by Bulger serving as an informant, tipping off federal agents about rival gangs. However, it becomes evident that this arrangement was more symbiotic than altruistic, as it allowed Bulger to eliminate his competition without judicial interference. The narrative sets the stage for a broader investigation into how deep corruption ran within the pillars of law enforcement that were supposed to be hunting him.

The courtroom becomes the battleground where Bulger's sordid past comes under scrutiny. While prosecutors strive to unravel the web of his crimes, victims and their families demand long-overdue justice. Tensions rise as testimonies reveal the troubling extent of FBI corruption, questioning whether Bulger was a puppet master or merely a pawn in a far greater scheme. Turning points in the trial force viewers to ponder the ethical disintegration within government agencies and leave open-ended questions about accountability. As court proceedings unfold, the documentary paints a chilling portrait of systemic failure and moral decay that facilitated one man's reign of terror, all while obscuring the clear lines between villain and victim.