First, he feels trapped in his life -- in the boring, daily grind of working in the candy store,...
The title “The Prison” is appropriate on a myriad of levels, for Tommy is trapped in a series of mental and sociological prisons, one nesting snugly within the next.
First, he feels trapped in his life -- in the boring, daily grind of working in the candy store, of living a routine life with no variation. “Time rotted in him,” Malamud writes; Tommy cannot escape the tight, ever-present pull of banal responsibility. It’s an inescapable cycle, forced upon him to a certain extent by himself -- he quit his vocational school at sixteen and took up with unsavory types, types that happened to be prolific in his underprivileged neighborhood. And, as he asserts near the end of the story, when contemplating the multigenerational consequences of this sort of a cycle,
“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.”
The candy store itself it a type of physical prison, but what it represents is also a prison: the economic constraints of a working-class existence, those invisible barriers that prevent a person from pursuing higher goals or validating him- or herself on a personal level.
Which brings us to another type of prison -- that of an unequal society. Tommy, as a boy, had had dreams of “getting out of this tenement-crowded, kid-squawking neighborhood, with its lousy poverty,” but at the time the story takes place he is still in that very same neighborhood, running a candy store with a woman his father arranged for him to marry, staying out of trouble because he doesn’t have the time or the energy to repeat the antics of his younger years. He never had the opportunity to escape the life of poverty and need that had circumscribed his childhood. “Everything had fouled up against him before he could.” This is an inherent flaw in our current society -- those who have little and need much are crowded into housing projects and forced into poorer areas, where opportunities for vertical mobility are slim and the temptation to fall into illegal habits compounds with the desperation to make ends meet and the resulting high availability of said unsavory jobs and habits. This forces individuals into a steady cycle of poor opportunity, desperate choices, and poverty. This is the cycle Tommy has fallen into -- he is to a certain extent a product of his environment, and only by the luck of having the right connections is he not in jail and instead running a candy store, even if it is “for profits counted in pennies.”
It is this cycle Tommy sees the little girl falling into when he discovers her stealing candy, and he feels a strong compulsion to talk to her, to prevent her from messing up her own life as he messed up his. And yet he cannot bring himself to speak to her because he doesn’t want his lesson to be misconstrued, which demonstrates yet another prison in which he finds himself -- he is paralyzed with anxiety and indecision, scared to be perpetuating the cycle himself through an inability to not get through to the little girl, such that his inaction ultimately leads to a messy and nonconstructive confrontation.
So, while Tommy may be free, or at least not be in jail like his old friend Dom, he is stuck in a multitude of prisons nonetheless -- the prison that is poverty and miscreant behavior, the prison that is indecision, the prison that is routine. And all these prisons feed off each other, and all these prisons are perpetuated over generations. And what’s worse is that all these prisons are willfully ignored by both the individuals who suffer in them and the individuals in power who could take steps to deconstruct them, thus contributing to their perpetuity.