Boss
By John Jeffire, first published in Coolest American Stories 2022
A car dealer’s deal with a drug dealer goes horribly wrong.
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Plot Summary
The man and his wife, who have been seeing each other since high school, have an agreement. After their marriage, they have agreed that both she and he can have sex with whomever they wish whenever they were away. Ever since a year into their marriage, they have lived in a condo by Lake St. Clair. The man works sales at his dad’s car dealership, and the wife works for a nearby television station. With lots of money, their lifestyle has been lavish with traveling and drugs. A few times, the man has gone to his wife’s television parties, in which he has gotten to meet his wife’s exuberant boss.
One day, the man realizes that he’s out of money to pay his cocaine dealer. Stubborn and embarrassed, he refuses to ask anyone else for money. He recalls an incident from his youth when he lost a fight, took on another fight per his dad’s instruction, and lost the second fight, after which he learned never to come crying to his dad or anyone else. At the car dealership, his dad is still ruthless and sees him not as a son but an employee.
Instead of seeking help, the man confronts his dealer, who presents a few ideas. The dealer proposes that the man uses his car dealership’s transports to carry the dealer’s drugs for him, after which he would be paid handsomely. Not only would the man get a lot of money, but he would also be helping his father’s business as well. All he needs to do is find the right driver for the job.
At his car dealership, the man strikes up conversation with a coworker whom he’s very attracted to. He asks her for a favor, specifically a driver who can secretly help him with transports in exchange for extra cash. She points him toward a driver who barely speaks English. When they meet, the driver understands the man’s instruction crystal-clear: the man arranges the transport, the driver takes it through to the dealer’s parking lot, and the dealer gives the driver extra money.
From then on, the transports happen successfully without any problems. The man makes a lot of money and spends it on whatever he wants. However, one day, the driver calls and says that a few gun-toting individuals stopped his transport and stole an expensive Jaguar. The man, now a vice president at his car dealership, struggles to figure out what to do on his own, as he can’t go to his father or the cops.
The man calls the dealer and tells him about what happened. The dealer says he knows which three people stole the Jaguar and that they’re down in Florida. He tells the man to go down to Florida, help the three people buy a vehicle using his acquisition credentials, and get the Jaguar back in return. The dealer then books his travel and sends him on his way.
In Florida, the man gets a rental car and drives to the meeting point. He meets a guy who escorts him off-road with two other cars. Soon enough, they pull into a forest. He meets the three people who have brought him here, who stole the Jaguar earlier: two brothers and a sister. The man asks for where the Jaguar is, and when the siblings don’t answer, he threatens to walk away, but they keep him there and pledge to uphold the deal if he complies. They explain that they’ll give him money to go to an auction and buy a bulldozer with his acquisition credentials, which they’ll use to terraform the land in the forest where they live. After he gives them the bulldozer, they’ll return the Jaguar. He agrees and spends the rest of the day having dinner around a campfire with the siblings before going to bed. In his makeshift room, the sister comes in and has sex with him.
By morning, the man is awoken by one of the brothers. He goes to the auction, buys the bulldozer, and takes it and its paperwork back to the forest. When they meet, the man asks for the Jaguar, after which he’s told that he’ll get it later. The man then threatens to withhold the bill of sale if he doesn’t get the Jaguar, but the siblings pull guns on him, saying that they don’t care about paperwork. Seeing that he’s been tricked, the man tries to negotiate, but the siblings say that the Jaguar has been sold off, hence why there was even money to buy the bulldozer to begin with. They reveal that the dealer has always seen the man as a pain in the ass and that no one would go looking for him if he went missing. One sibling presses his gun to the back of his head and tells hm to keep walking.
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