Tom loves his wife, but he has become so obsessed with achieving success in his business that he has been taking her for granted. Clare appreciates the fact that he is working hard for her benefit as well as for his own, but she tells him:
"You work too much, though, Tom--and too hard."
Proof that he is working too much and too hard is dramatized in the story. Tom is sending his wife off to the movies by herself because he wants to work on an Interoffice Memo he hopes will get him noticed and appreciated. He is intensely ambitious and determined to succeed in a harshly competitive world.
It isn't until Tom is out on the ledge eleven stories above the street that he realizes how his values have become confused. His wife was the most important thing in his life, not his work.
He wished, then, that he had not allowed his wife to go off by herself tonight--and on similar nights. He thought of all the evenings he had spent away from her, working; and he regretted them. He thought wonderingly of his fierce ambition and of the direction his life had taken; he thought of the hours he'd spent by himself, filling the yellow sheet that had brought him out there. Contents of the dead man's pockets, he thought with sudden fierce anger, a wasted life.
Clare is described by the author as "a slender, very pretty girl with light brown, almost blonde, hair." It is Tom's realization of his love for her that gives him the courage to get back to the window of his apartment, where he can see and appreciate the modest domestic beauty of the unattainable home he shared with his wife. Thinking of her gives him the nerve and the strength to break the window with his fist and finally to crawl back into the living room. When the document for which he risked his life sails out of the window again, he laughs at the irony of it and goes off to find his wife at the movie theater.
The best thing about "Contents of the Dead Man's Pocket" is the feeling the reader gets of being out on an extremely narrow ledge high above New York City. Tom doesn't dare to look down. He knows he would get dizzy and fall to his death. But finally he is forced to look down for one instant in order to be able to pick up the paper.
At the same instant he saw, between his legs and far below, Lexington Avenue stretched out for miles ahead. He saw, in that instant, Loew's theater sign, blocks ahead past Fiftieth Street; the miles of traffic signals, all green now, the lights of cars and street lamps; countless neon signs; and the moving black dots of people.
The story seems a bit dated now. Many people used to live in residential hotels in Manhattan like the one described in the story. They were cheap and convenient. Most of these buildings have been torn down or converted to transient hotels, and married couples like Tom and Clare would not be able to afford to live in them. The residential hotels were getting old. Readers of the time would recognize the author's description of the old double-sash windows that wouldn't open and the fact that
Most of the putty, dried out and brittle, had dropped off the bottom edging of the window frame...
But workaholic husbands and neglected wives are still part of modern life.