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 called Robinson, is a schoolteacher from Las Vegas whose wife was murdered after speaking to the FBI about, and agreeing to testify against, the 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.
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. However, he quickly recognizes that a fake detour would not serve, partially due to a lack of co-conspirators but also because he believes Dolan would sense the detour was a trap and be on his guard. He 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 summer job with his road crew. 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. After several weeks of this, 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.
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 30-mile stretch of highway scheduled over the 4th of July weekend, and begins to make preparations to put his plan into action.
He 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 puts the jackhammer to work, 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, and waits for Dolan's Cadillac to appear on the horizon.
As the car finally appears several miles down the road, he quickly hides the DETOUR markings, and the Cadillac proceeds down the road. The car disappears into the hole, and Robinson soon learns that his trap has worked perfectly -- the car's doors are pinned closed, and Dolan is locked in. After only a few sentences, Dolan is incredibly able to identify his captor, and soon makes a proposal: one million dollars, and a personal guarantee of safety, if Robinson lets him out. Robinson's counter-proposal is that, if Dolan screams loudly enough, he may be freed. Of course, this does not happen, and Robinson proceeds with the burial. As he fills the hole, he can hear Dolan's crazed laughter. The dirt is in place by Sunday evening, and Robinson spends Monday replacing the asphalt sections. He returns home by eleven o'clock that evening.
Robinson's back was severely injured by his exertions, but this is the only repercussion. Dolan is never found, and the mental anguish associated with his wife's death soon fades.