Dolan's Cadillac is the first story in Nightmares and Dreamscapes, and was originally published in the February-June 1985 issue of Castle Rock. It describes one man's conception and execution of an intricate revenge plan against a local crime boss who killed his wife.
The initially unnamed protagonist, whom we eventually learn is named Robinson, is a schoolteacher from Las Vegas whose wife was murdered after speaking to the FBI about, and agreeing to testify against, a powerful crime boss, Dolan. His obsession with revenge leads him to follow Dolan (around both Las Vegas and Los Angeles) for several years, and on one of their trips from California to Nevada, he begins to formulate a plan. Small and inconsequential as he is compared to the powerful gangster, Robinson is never noticed by Dolan or his bodyguards.
A highway detour reminds Robinson of a movie in which a group of bandits rob an armored car after posting signage for a fake detour that directs the car onto an isolated side road. Yet a fake detour would not work against Dolan, Robinson realizes, both because he has no one to assist him and because Dolan is an intensely vigilant man. Any fake detour would be detected by Dolan's keen survival instincts, and Dolan would have his driver change course and simply get away. Robinson then surprises himself with a sudden thought: "Don't try to fool him with a fake detour; fool him with a real one."
He soon formulates a plan, and slowly begins to put it in motion. His first steps are to buy a health club membership and a Nautilus machine. He begins fervent workouts, to the amusement of his colleagues. Harvey Blocker, a foreman with the Nevada Highway Department, is similarly amused when Robinson applies for a job with his road crew -- such a job means working during the blazing heat of the desert in the summer months. Blocker's initial reluctance to hire the scrawny third-grade teacher is minimally lessened when Robinson makes a bet of sorts, wagering his great-grandfather's watch that he will be able to last the summer, and he is given his first assignment -- filling potholes while walking along behind a dump truck filled with hot asphalt. After several weeks, Blocker becomes increasingly impressed with Robinson's tenacity, and soon promotes him to operator of a front-end loader, a job Robinson holds until the end of the summer. Robinson recounts how he barely remembers doing the hot patch job but is spurred to persevere by the memory of his murdered wife.
Aside from the physical benefits of his grueling summer job, it also gets his name on the mailing list for the Highway Department. Each month, he scans the upcoming roadwork calendar for just the right repaving job. After nearly two years, he eventually notices a isolated 30-mile stretch of highway scheduled over the 4th of July weekend, and begins to make preparations to put his plan into action. He first consults a friend of his who tells him how to design the perfect trap for Dolan's car, though Robinson tells his friend he's writing a story about trapping an alien spacecraft. He then purchases an old van, and loads it up with an assortment of equipment and supplies. Late Friday afternoon, he makes his way to the detour and begins his work. He marks out a rectangular block on the asphalt, and uses a jackhammer, cutting 2' x 2 1/2' sections out of the road. After several hours of backbreaking labor, he gets the asphalt cut and moves to the "heavy equipment" phase of his plan. He hot-wires a front-end loader, and begins the excavation. His obsession with getting the slope perfect, combined with his rapidly stiffening muscles, lengthens the job, and by 9 am Sunday morning, he has done all he can do. He covers the hole with canvas stapled to a wooden frame, and waits for Dolan's Cadillac to appear on the horizon.
A Cadillac similar to Dolan's comes along, and Dolan nearly activates the trap, but his wife's voice stays his hand, telling him the car is not gray, but green, and that Dolan has never owned anything but a gray Cadillac in his life. When the real car comes into view, Robinson quickly hides the "DETOUR" signs, and the Cadillac proceeds down the road. The car disappears into the hole, crashing against the far wall, crushing the engine. Robinson discovers that his trap has worked perfectly -- the car's doors are pinned closed against the walls of the pit and with the engine destroyed, the electric windows cannot be opened. Dolan quickly identifies Robinson and nearly kills him by firing his revolver through the roof of the Cadillac, but ultimately offers one million dollars and a personal guarantee of Robinson's safety in exchange for his release. Robinson's counter-proposal is that, if Dolan screams loudly enough, he may be freed. None of Dolan's attempts are judged loud enough, and his sanity steadily erodes as Robinson proceeds to bury him alive. Robinson uses heavy equipment to finish moving the dirt by Sunday evening and spends Monday replacing the asphalt sections. He returns home by eleven o'clock that evening. After he's finished, a repaving crew moves in, tears up the road and lays a new one but never notices that Robinson's excavation took place.
Robinson's back was severely injured by his exertions, causing him horrific pain. He sees a specialist who tells him he needs surgery and is sent to Kansas City. Right before Robinson awakes, he has a dream where Dolan has come back from the dead and nearly kills him. At one point Robinson travels out to the desert and urinates on what he believes is the spot where Dolan and his Cadillac are buried. Dolan is never found, and the mental anguish associated with his wife's death soon fades.
The story was released as a film by the same name in 2009 starring Wes Bentley and Christian Slater.