Hurstwood spends the summer and fall moving about the lower part of the city, drifting from one cheap hotel to another. Finally, when he has spent all the money he received for the furniture in the apartment, he walks to a large Broadway hotel to find a job. His story interests the sympathetic manager, who gives him work as an odd-jobs man and a place to sleep. He must take orders from cooks, porters, and firemen. On an errand one February day, he gets a thorough soaking and chill which result in pneumonia. Until the following May, he recuperates at Bellevue Hospital.
Hoping to meet Carrie outside the theater one evening, Hurstwood misses his chance to see her when she arrives suddenly and rushes inside. With an aching stomach and sore feet, he joins a group of fellow unfortunates and is provided free lodging for the night through the efforts of a self-appointed social worker.
The indignity of Hurstwood's situation is made more severe by the remnants of pride that are left to him. In fact, weakened in body and mind, he seems to be in a state of chronic shock. Often he finds himself repeating out loud snatches of conversation and the tag ends of jokes he remembers from the days when he had been a successful manager in Chicago. "As the present became darker, the past grew brighter, and all that concerned it stood in relief."
The man manages to survive for a time by learning the science of face reading. Some people, he discovers, are more easily touched for handout than others. In the incident outside the theater in Chicago Hurstwood ignored a panhandler seeking money for a night's keep. It was finally the good-natured Drouet who gave the man a dime, while Hurstwood continued his animated conversation with Carrie. Now, through a series of fateful reversals, he is the panhandler.