Portrait of a Young Man Drowning

The novel takes place in the slums of Brooklyn during the Great Depression, and follows the narrator, Harry Odum, from his early childhood to his death. His father, Hap, abandons the family, leaving Harold to be raised by his mother, Kate. Harold falls in with his friends from the neighborhood, who take him along to participate in petty crime. He soon join up with "Bug", the neighborhood kingpin, and moves his way up through the local crime syndicate. He eventually becomes the neighborhood mob's killer for hire. Meanwhile, Kate spirals deeper into alcoholism and mental illness, and grows ever more possessive of her son.

Through it all, the only person Harold feels any love for is his mother; he develops an Oedipal complex and an inability to sexually relate to anyone without resorting to his alter-ego, Madden. In the guise of this other self, he rapes a local girl, Iris, with whom he later falls in love.

Harold attempts a relationship with Iris, but Kate threatens her away during a family dinner. The next day, Harold flies into a psychotic rage and rapes and kills his own mother, who he thinks committed suicide. A dazed, traumatized Harold then goes for a ride with some of his partners-in-crime, who are afraid he, in the mental state he is, lets information of any crime that might involve them, and make sure he never talks about it.

The novel was adapted into the 1997 film Six Ways to Sunday.