Gary is furious - Tucker was supposed to help him paint the den, but left him to shoulder the task alone. As the others arrive, Sam delightedly accepts an unspoken offer from Gary, who's none the wiser. Tucker hastily prepares to start his story - a tale of trust; a need, in dire circumstances, to rely on one specific person - perhaps the one you least expect. Submitted for the approval of the Midnight Society, he calls this story "The Tale of Prisoners Past."
A tour-guide, garbed as a prison officer, narrates the great prison revolt of 1922. The visiting class inspects the prison's souvenir stand. Chess Club president Jason browses t-shirts. Scott poses for a photo. The two had had nothing to do with one another, until Jason's mother married Scott's father.
From Jason, Scott takes five dollars. Jason snatches it back, and runs down a set of stairs into darkness. Jason follows. As they pass a cell, Jason jumps at the unexpected sight of a man inside. The bearded, eye-patched man introduces himself as One Eyed Jack, and laments having done more than his time for the mistake of robbing a bank. He pleads to be let out. Scott opens the door. From no visible source, a shadow descends over the cell, plunging it into darkness. When the shadow lifts, One Eyed Jack has vanished. From behind them, he demands they both get in the cell. On the count of three, Jason and Scott run.
In their shared bedroom, Jason paces wonders whether to report their ghostly adventure to the police, prison officials or newspapers. Scott puts the encounter down to a new exhibit.
Late that night, Jason goes to close the bedroom window. From outside, a hand, clad in the sleeve of a prison uniform, seizes his pyjama shirt. Outside, the desolate figure of One Eyed Jack implores him to come back. Jason cries out in horror. Scott grabs him from behind, and yells in fright. As the boys break his grasp, the apparition floats back into the night.
Next day, at the library, Jason and Scott, by microfilm, peruse old newspapers. In 1942, One Eyed Jack, convicted of robbing the First Federal Bank, escaped. As to his evasion of top level security, prison officials were baffled. A later article, from 1945, marked closure of the prison - whose only blemish was the escape of One Eyed Jack, who remained at large. His daughter, Elma Briggs, noted to live on Linden Place, demanded access to prison records, and was dismissed as unbalanced.
At Linden Place, Jason and Scott pay a call on Elma Briggs. Jason asks if One Eyed Jack is her father. On two walking sticks, she bustles onto the doorstep, pokes Jason with her walking stick, rails against persecution by opportunistic humorists, and orders them off her property.
That night, Scott spitefully mocks Jason's fretful indecisiveness. Jason angrily shoves him against the bedroom door. Scott grimaces fiercely. Behind him, seamlessly through the wood of the door, comes a yellow-glowing, prison uniformed arm. It enfolds Scott's chest. As Scott is pulled against the door, his outline briefly glows yellow, as his body passes seamlessly through the wood. His shoes remain on the carpet.
Resolved to do something, Jason takes a flashlight, and sets off...
Through the open door of One Eyed Jack's cell, Scott lies face down on the bunk. Touched on the shoulder by Jason, he wakes with a startled gasp. Before them, the door slams shut. With a squeak, a large grey rat saunters past the toilet. Scott groans in distaste. Jason realises it must have gone into a hole.
Suddenly excited, they pull the away the frame on which the toilet is mounted, revealing what looks like a partially bricked up ventilation shaft. They crawl, face down, through the cobwebbed tunnel. On the floor before them, face up, lies, in rotted clothes and an eyepatch, a human skeleton.
As the boys writhe in panic, the floor beneath them gives way. They fall through a chute, and onto a broad sheet of cardboard, followed closely by the skeleton. Before them materialises the faded, yellow-shimmering figure of One Eyed Jack. He ruefully notes his brutal death, and asks the boys to tell Elma of his fate - proof thereof lies in the skeleton’s pocket. With a final word of thanks, he fades.
In the pocket lies a creased, black and white photograph, of a younger One Eyed Jack, with his arm around a smiling small girl.
The boys present the photo to Elma Briggs, who heartily thanks them for this touch of emotional closure.
As to Sam's excitement, still-angry Gary is still none the wiser. Tucker hastily explains having been unable to help him paint the den for having been stuck in line for five hours, waiting to buy two Lollapalooza tickets, which, with a "Happy Birthday," he hands to a stunned Gary, who, moved, thanks his brother.
This episode provides examples of:
- Air-Vent Passageway: Deconstructed. One Eyed Jack tried to use one to escape, but died in the attempt.
- Bait-and-Switch: Jason and Scott assume the ghost followed them to the library and the person has a grey and white striped attire. Turns out it's the librarian.
- Beard of Sorrow: One Eyed Jack's grey, matted beard poignantly evokes his remorse and isolation.
- Break the Haughty: After taunting Jason for his timidity, Scott, when they’re both trapped in the cell, is embarrassingly horrified by the sight of a rat.
- The Bully: While not constantly, Scott sneeringly lords it over Jason, and illicitly uses his money.
- Bully Turned Buddy: After their shared ordeal, Scott shows a civil, friendly regard for his stepbrother.
- Buried Alive: Unbeknownst to anyone, One Eyed Jack died in the ventilation shaft.
- Cowardly Lion: While readily fretful, Jason aspires to prove his capacity for bravery by going to rescue Scott.
- Dead All Along: On first encounter, One Eyed Jack looks like a flesh and blood prisoner - or a staged depiction thereof. His instantaneous disappearance and reappearance hint his ethereality.
- Dem Bones: In the ventilation shaft, Jason and Scott run into One Eyed Jack's skeleton. They get quite a fright.
- The Ditherer: Jason has a tendency to anxiously repeatedly evaluate options. Scott gives him a hard time about it.
- Even Mooks Have Loved Ones: One Eyed Jack implies to greatly regret having robbed a bank, and seems deeply sorrowful at having been separated from his daughter.
- Fire-Forged Friends: Trapped in an ancient prison cell, Jason and Scott find a mutual esteem in their shared ordeal.
- Ghostly Goals: One Eyed Jack, in his solitude, wants his remains to be found, and for his now-aged daughter to know of where he was all these years.
- Laser-Guided Karma: Being seized and dragged off by a pair of spectral arms quickly and thoroughly knocks out of Scott the bravado with which he'd planned to punch Jason.
- My Greatest Failure: One Eyed Jack regrets having robbed a bank, and having died in custody, leaving his daughter unaware of his whereabouts.
- Please, Don't Leave Me: One Eyed Jack follows Jason and Scott to their house, reaches through the window, and beseeches them to return to his cell.
- Supernatural Light: On contact with earthly matter, and when nearing departure, One Eyed Jack's spectral body exudes a yellow glow.
- Took a Level in Kindness: Initially spitefully contemptuous of his anxious, scholarly stepbrother, Scott's shared ordeal with Jason, in which they help each other, sways him to civility.
- Tragic Keepsake: Inverted. Directed to its location by One Eyed Jack's ghost, Jason and Scott present Elma with a photo of herself and her father, revealing both his long-lost whereabouts, and reach from beyond the grave to indicate as such.
- Wham Shot: While going through the ventilation shaft, Jason and Scott find something...One Eyed Jack's skeleton.
- Vengeful Ghost: Subverted. One Eyed Jack seems to be one at first, going as far to take after Jason and Scott and eventually kidnaps the latter, but it's all so they (and his daughter) can find out what really happened to him. He apologizes to them afterwards.
