Willie Keith says goodbye to his mother before entering Navy midshipman's training school. Willie is a graduate of the Princeton class of 1941. He majored in Comparative literature and spent most of his time playing the piano at parties. He is somewhat chubby and good looking, with red hair and an agreeable face. Willie's mother is "a large, wise, firm woman, as tall as her son, and well endowed with brow and jaw."
The two drove from the Keith home in Manhasset in the family Cadillac, despite Willie's desire to take the train. The midshipman's school is located in Furnald Hall, a former dormitory of the Columbia University School of Law. Willie receives instructions from the Navy chief at the door and, stepping through the door, enters military life.
As Mrs. Keith watches her son disappear, she realizes that she forgot to give him money, and runs to the door to try to reach him. The chief stops Mrs. Keith and informs her that she can see her son during visiting hours on Saturday. This is not good enough for Mrs. Keith, however, and she gives the chief one hundred dollars to give to Willie. Shocked by the enormity of the sum, the chief promises that he will get the money to Willie. When Mrs. Keith returns to her car, the chief pockets the money for himself.
Willie Keith is quickly introduced to the ways of the military. He is stripped down and given inoculations and a physical. The medical examiners discover that Willie has a lardosis of the back, an unusually quick pulse, and an inability to touch his toes. He is almost declared physically unfit for Navy duty, but his Princeton degree saves him. Willie reports to Room 1013, his new home. There he meets his roommates, Edwin Keggs, a good-natured high school algebra teacher, and Roland Keefer, a fat, confidant, Southern civil servant. Keefer naps, and Keggs explains to Willie that in three weeks one-third of the class would be "bilged" straight to the Army. Keefer wakes up and the three bond over this common fear of being sent to the Army. They are eventually given bedding and settle into sleep.
Gifted with one of the highest draft numbers in the country, Willie had not worried about military service for the first year of the war. Willie ignored his family's desire to see him continue his studies of comparative literature, instead making minimal wages in trashy New York piano bars. Auditioning new acts at the Tahiti, Willie had met his first love, May Wynn. She catches Willie's eye by auditioning with Mozart instead of with the usual lounge faire. By means of her uniquely honest voice and attractive physique, May wins the job at the Tahiti. Willie invites her to dinner, taking her to Luigi's, a homely Italian pizzeria. There he learns that May's real name is Marie Minotti. His reacts to this with "a mixture of relief, pleasure, and disappointment." Willie is infatuated with May Wynn's honesty, ignorance, and attractiveness, but the discovery of her Italian family name and humble upbringing means she will not be accepted by Willie's upper class family. On the other hand, the knowledge that marriage is impossible liberates Willie from fear of commitment, and he is excited by the prospect of simply having fun with this girl. Willie feels confident in his superior education and upbringing, and woos May Wynn with his knowledge of literature and the arts. May Wynn also realizes the impossibility of a successful relationship between them, saying, "Well, Princeton, obviously we can never hit it off." Mostly due to Willie's perseverance, they continue to see one another. They share expensive dinners, visit museums, and kiss in the back of taxis. When Willie is contacted by the draft board, he decides to enlist in the Navy officer's school.
When Willie Keith is initially introduced in The Caine Mutiny, Wouk portrays him as a boy who floats through life, an upper-class stereotype: excessively rich, overeducated, womanizing, manipulative, self-serving, and directionless. As Willie's history is developed, we watch him waste his time at Princeton playing ditties at parties, then throw away his education by forsaking graduate school in order to become a lounge pianist, a job that would not even support him financially without the money his mother gives him. Willie uses his position of advantage to maneuver May Wynn into a relationship with him, which she initially resists. He stands to lose nothing while having a good time, but the relationship will inevitably result in heartache for May. Willie also initially shrugs off his duty to his country in wartime, opting to use his influence to enroll in an officer's training program instead of being drafted into the Army. Willie initially strikes us as a difficult character to like.
We feel some sympathy for Willie because of his intelligence and his eccentric lifestyle. Willie's personality is constantly at war with the expectations dictated to him by his upbringing. He is supposed to dislike Jews and Italians, he is supposed to be completely subordinate to his parents, and he is supposed to care for nothing but money and influence. Willie quietly resists these rules, however. Willie becomes more of an individual in response to his military training and his relationship with May Wynn. He likes Marty Rubin despite his religions, and repeatedly defies his parents.
Willie has very complex relationships with his parents, the depths of which are first touched on during the scene when Mrs. Keith drops her son off at Columbia. Mrs. Keith, though well-meaning, tries to shelter Willie from reality. She would prefer to hand him everything that he needs in life, rather than allow him to become independent, as evidenced by her attempts to get money to Willie after he enters the service. At this point in the novel, her efforts appear to come more from a conservative desire for Willie to lead a proper upper-class lifestyle than from fear of losing her only son. Mr. Keith is mostly absent from the events of this part of the book. The only interaction between him and his son comes in a flashback in which Willie considers enrolling in the Navy at the beginning of the war. Showing no opinions of his own, Mr. Keith simply warns Willie that going into the Navy would upset Mrs. Keith. Other than this episode, Willie's father quietly plays his role as the family breadwinner, and does not make up a noticeable part of Willie's support network.
May Wynn is Willie's opposite. She is poor, uneducated, and Italian; she speaks her mind with honesty, perception, and color. She is also more interesting than Willie is, having passed up a free college education, as we find out later, in favor of the money available to her in the lounge singing business because of her talent and figure. It is almost certain that she foregoes college in order to help her family with their financial struggles. She picks up immediately on the impossibility of commitment between herself and Willie, but still allows their relationship to develop. This indicates that like Willie, at least at first, she is solely interested in having a good time.