|Status||In FBI custody|
|Location||With the FBI|
Hennessey's files are a set of incriminating files used by police captain Dick Hennessey to frame, blackmail and extort the criminals and innocent people of Grant City.
As part of his plans for power, Dick Hennessey uses his power to blackmail, frame and extort the criminals and innocent people of Grant City. To this end, he keeps a collection of files on each of his victims cleverly hidden as police evidence inside the GAC Police Station. According to Mayor William Pinnacle, Hennessey's files contain not only enough evidence to put Pinnacle in prison but "every criminal on this side of the river."
After his father is murdered, Jack Slate is framed for the murder of Augie Blatz by Hennessey. Escaping from his execution, Jack investigates his father's murder, eventually leading him to discover Pinnacle's gold mining operation and to come to the conclusion that Pinnacle is his father's killer. When Jack confronts Pinnacle at the Iron Point Penitentiary, Pinnacle instead reveals the truth about Hennessey and offers a deal: Jack helps him get rid of Hennessey and his files and Pinnacle will get him pardoned. Though reluctant, Jack realizes that Pinnacle is telling the truth and decides to ally with him to steal the files.
As part of their plan, Pinnacle calls Hennessey and claims that Jack is chasing him around the prison, causing Hennessey to take most of GAC there to kill Jack. While Hennessey and GAC are distracted, Jack breaks into their police station and fights his way to the evidence room. There, he discovers a bundle containing Hennessey's files on himself, his father, Pinnacle, Augie Blatz, Gloria Exner, Fahook Ubduhl and Preacherman Jones. While Jack knows he could likely find more if he continues searching, he decides that what he's got is more than enough and calls Gloria Exner to turn the files over to her instead of Pinnacle so that Pinnacle can't get away with his crimes.
After escaping the police station, Jack meets with Gloria at his father's grave in the Grant City Cemetery to turn the files over, telling Gloria that they are all she needs to beat Pinnacle in the mayoral election and send him to prison. Jack suggests that Gloria take the files to the media since the police are in on it, but Gloria reveals that she already knows and pulls a gun on Jack. Gloria tells Jack that she's pulling out of the election and has made a deal with Pinnacle to give him the files in exchange for her own safety, stating that what's in them could get her killed. Before the situation can devolve further, Gloria is murdered by Jack's friend Hildy Razwell who is now working for Fahook and has been promised a great deal of money in exchange for the files. After warning Jack to stay out of everything for his own sake, Hildy drives off with the files chased by Jack in a hearse.
Hildy travels to Fahook's hideout at Warden Air Force Base where he is preparing to leave the country until things cool down and turns Hennessey's files over to him. As Jack watches, Fahook looks through the files, intrigued by the contents and Hildy is annoyed that Fahook plans to pay her with a few bars of gold rather than cash. As the two argue, Pinnacle comes up behind Hildy and murders her. Enraged, Jack pulls Pinnacle out through the window to get revenge and Fahook takes the opportunity to flee with the stolen files.
After killing Pinnacle, Jack chases down Fahook's plane and boards it to stop Fahook and get the files back. Fahook eventually shoots his pilot in order to crash the plane and attempts to parachute out of the cargo door with the files to escape. Jack manages to send Fahook falling from the plane to his death, but not before he recovers the files. After disengaging the auto-pilot, Jack calls reporter Kip Waterman to meet him after the plane comes down for "the story of the century."
Following the plane crashing on the runway at Warden Air Force Base, Jack drives off with Kip in a news van and hands him Hennessey's files, calling it Kip's Pulitzer Prize. Jack tells Kip that once he reads the files he will understand the story when Kip asks him what's in them. Kip reads the files with a look of shock on his face and promises to get them on the 10 o'clock news and to report Jack dead in the plane crash in return.
At the Bay Bell, when finally confronting Jack face to face, Hennessey demands to know where his files are, but all Jack will tell him is that he gave them to a friend for safekeeping. At that moment, Kip comes on the news on TV announcing that evidence has come to light implicating key officials in City Hall and the Grant City Police Department in capital racketeering and organized criminal intent with Hennessey chief amongst them. Hennessey realizes what Jack did with his files and is enraged. When the FBI arrives, the files are presumably handed over to them by Kip.
Sometime later, Preacherman Jones, wrongly incarcerated at the Iron Point Penitentiary, listens to a news report by Kip on how Jack's body has been identified amongst those from the plane crash. Opening a package he has just received, Preacherman discovers a bar of gold, a newspaper, a postcard from Jack reading "Faith, Padre. Faith" and the file on him that Jack had stolen from Hennessey which is evidence capable of exonerating Preacherman. Realizing what Jack did, Preacherman calls out to a guard to turn the file over to.
- While Jack only takes the one bundle of files, its heavily indicated that there are more files that he did not take. Pinnacle mentions Hennessey having enough evidence to blackmail many criminals and send them to prison while Jack suggests that if he searches harder, he'd probably find more evidence but doesn't bother as he has what he needs. There is also another bundle of files next to the one Jack takes but its unclear if its related to Hennessey's files or is actual police evidence.
- Many people died over possession of the files including Gloria Exner, Hildy Razwell, William Pinnacle and Fahook Ubduhl.
- Jack sending Preacherman Jones the evidence from Hennessey's files to exonerate him is in keeping with Jack's promise to get Preacherman out of jail if their plan to have Jack escape the electric chair works.