How does Malamud memorably portray suffering in "The Prison"?

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In the story, Malamud memorably portrays suffering by highlighting the many instances Tommy Castelli is thwarted and defeated in his efforts to improve his life. The author focuses on Tommy's unhappy marriage, unfulfilling career, and crippling sense of helplessness.

In the story, Malamud portrays Tommy as an emasculated, hen-pecked husband who can't seem to achieve a measurable level of happiness in his life. Every business enterprise Tommy tries to engage in seems to fall flat: either his wife, Rosa, finds out about it and berates him for it, or the business schemes fall apart anyway.

For instance, Tommy once earned fifty-five dollars from secretly taking in some lottery punch-boards a syndicate was distributing in the neighborhood. Tommy manages to hide the money from Rosa (who detests the idea of gambling); however, the syndicate is written up in the newspaper (perhaps for business irregularities), and the punch-boards disappear. In another instance, Tommy manages to get a lottery machine into his store. When Rosa discovers it, she "wouldn't let up screaming."

To make matters worse, Tommy's father-in-law later comes in and smashes the machine apart with a "plumber's hammer." Both Rosa and her father berate Tommy for his entrepreneurial spirit. Tommy tries to placate Rosa by explaining that the earnings from the machine will allow him to buy a television so that he can watch the fights without going to a bar. He also tries to explain that, since everyone gets a roll of mints for every nickle played, it can't conceivably be called gambling. However, his explanations fall on deaf ears; to make matters worse, the police begin raiding stores for lottery machines and giving out summonses for them not long after his own machine is destroyed.

Tommy's store is the only one without a lottery machine at the time of the raid, but he still grieves for the loss of his own machine. All he knows is that he has very little personal agency in his own life; the candy store has been financed by his father-in-law, and he must placate both his wife and his father-in-law in all matters pertaining to the business. This dismal situation encapsulates why Tommy feels like he's living in a prison. Even his name has been changed from Tony to Tommy by Rosa. He's a man who can't even hold on to his name, let alone order his own life as he sees fit.

Tommy later tries to save a young girl (who's caught shoplifting in his store) from a life of crime, but he sees his efforts thwarted by Rosa and the girl's mother. Accordingly, Rosa, in her anger, assaults the young thief. Distressed beyond belief at his wife's abusive behavior, Tommy turns on Rosa. He slaps her across her mouth to stop her from carrying on, but the hit is harder than he intends. When the young thief's mother comes in and is apprised of her daughter's actions, she proceeds to slug her daughter across the mouth and to drag her home. Despite Tommy's good-faith effort in standing up for the young thief, she shows no gratitude and instead, sticks her tongue out at him before she leaves the store. This depressing state of affairs sums up Malamud's portrayal of Tommy's life. It's a life filled with missed opportunities, untold misery, and countless disappointments.

You never really got what you wanted. No matter how hard you tried you made mistakes and couldn’t get past them. You could never see the sky outside or the ocean because you were in a prison, except nobody called it a prison, and if you did they didn’t know what you were talking about, or they said they didn’t.

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