A Bad Man by Stanley Elkin

"Sentenced to a year in jail for providing his customers with everything they needed - drugs for the nervous, abortions for the unintending, guns for the crazed - department store owner Leo Feldman finds himself in a Kafkaesque prison. Labeled a "bad man," Feldman is treated as a fool, made to wear a clownish version of his business suit with oversized button holes too big for the buttons and miscut legs and pockets. While incarcerated, he's forced to come to terms with his criminal self - a man always on the make, one who can't avoid overselling to the poor and lying to the trusting - in this grey-stone purgatory run by a sadistic prison warden who enforces a set of elaborate, ever-shifting rules."