The story follows Whitey, an aging merchant mechanic who has docked for a few days in San Francisco, where he has a relationship with a family who lives there.
In a dimly lit bar in San Francisco, a very drunk Whitey (though we do not yet learn his name) tries to understand his surroundings. As he searches for some company, he also counts his money, unsure where it all went. He reflects upon the jacket, the shoes, the cab rides, the fines, and all the alcohol he has paid for. Throughout his time in the bar and the story to follow, certain thoughts (set aside in italics) keep popping into his mind, the foremost of which is the phrase: "Hey Sailor, What Ship?" (13).
Instead of going to visit his friends, "Lennie and Helen and the kids," he tries to buy another drink (13). When the bartender refuses to advance him any more credit, Whitey stumbles off to Pearl's, another bar, but encounters his friend Lennie, who ushers Whitey into his car. As Lennie drives him to his (Lennie's) house, Whitey asks Lennie to stop somewhere so he can buy either a bottle or presents for Lennie and Helen's kids. Lennie refuses.
Helen and Lennie had expected Whitey four days earlier, but he never arrived. He meets Helen, who looks more gray than he remembered, at the doorway, and then the children surge around him, welcoming him home. They are Jeannie, Allie, and Carol. When Helen grows emotional over Whitey's sickly appearance, the oldest daughter, Jeannie, forces her to head into the kitchen. When Whitey remarks to Lennie about Helen's appearance, Lennie suggests that Whitey looks poorly as well. The girls want to play with Whitey, but he chooses to rest and sober up.
Lennie and Helen invite their friend Chris to examine Whitey. Chris had idolized Whitey's adventurous life when he was a young man, but has since become a doctor. After the examination, the adults give Whitey some sleeping pills so he can rest. The youngest daughter, Allie, visits Whitey's room to tell him about a nightmare. While she snuggles next to him, he reflects on all the poverty-stricken children he has seen during his time traveling around Asia.
As Allie sleeps next to him, Whitey regales Lennie and Helen with stories of his time abroad, of different illustrious beatings in London, Marseilles, and Shanghai. Before he drifts off, Jeannie visits him, and he notes how much she looks like Helen once did. Jeannie talks about her homework, and asks Whitey his traditional greeting, "Hey Sailor, what ship?" (23). She traces his newest scar with her finger, and then Helen insists they leave Whitey to sleep.
He sleeps fitfully, partly because he is accustomed to the strange noise and movements of the ocean. When he wakes up, he finds a note telling him that breakfast is in the refrigerator and that the children are coming home from school to be with him. Helen signs the note, "Love" (24).
Whitey notices the scarcity of food in the pantry, and deduces that the family is still struggling financially. He daydreams about bringing home lots of groceries and presents for them. For reasons he does not understand, he dresses hastily and leaves.
Five days later, he returns to the house, this time loaded with groceries and presents. The children grow hyper, and Whitey insists they have a drink with him while he jokes about sailors. Helen insists he wait until after dinner to hand out the presents. He eats up Helen's food, but she refuses to accept the ten dollars he offers in exchange. As Helen washes the dishes, he makes fun of her and bounces Allie on his knee, singing a song about sea-life to her at the same time.
Once dinner is complete, Whitey asks Helen to bring in the presents, and he pours himself a drink. Lennie warns him not to drink too much, and Helen insists the children get ready for bed before they receive presents. They complain, wanting to play more with Whitey, but he promises he is staying awhile and then gives each of them a dollar. He tries to take another drink, but Lennie stops him.
Jeannie warns him not to speak so colorfully around her friends, who are coming over for a visit, and he gives her ten dollars as a mock-apology. Lennie insists she return the money, and she runs upstairs after tossing it at him. Lennie then insists Whitey stop throwing his money around.
Whitey accuses Lennie of acting "holier than the dago pope," and Lennie counters that he must stop cursing and drinking (29). They calm down and drink a while, and then Lennie asks for more details of his recent trip.
Right as Whitey begins, Jeannie returns downstairs to stiffly thank him for the earrings he bought her. Whitey tries to give her ten dollars again, and reminds her that she is his 'wife,' since she had once playfully announced their betrothal when she was four. When she shies away from him, he tries to rectify the situation by asking about the other presents he bought her. She returns the earrings to him instead of replying, and then announces she will wait for her friends outside.
Helen calls Jeannie into the kitchen as Carol and Allie rush to Whitey, thanking him for their presents. He is drunker now. He had given Carol an album with a picture of himself at age sixteen, looking much less worn and battered. As they talk, Whitey loses track of his surroundings, calling himself M. Norbert Jacklebaum and complaining about being punched. Allie insists nobody is punching him, and reminds him his name is actually Michael Jackson, confused why he calls himself a different name.
Carol asks him to sing "Crown 'n Deep," but he has difficulty remembering it. He confuses Carol with Jeannie, but finally begins to sing "Crown 'n Deep," a song from the Philippines known as "The Valedictory" (32). He loses track of the song as he sings, until he is "inaudible" (33). Noting that Whitey is now "swaying," Lennie sends the children to bed (33).
In the kitchen, Jeannie berates Helen for letting Whitey use foul language around the younger children, and asks why she had to return his money. Helen explains that they cannot accept his hard-earned money, but Jeannie writes him off as just a "Howard Street wino" (34). Helen tries to explain that they have a long history with Whitey, and that he has always been good to them. She tries to remind the girl how Whitey had to go to sea when he was young, and about how he saved Lennie's life in a strike in 1934. However, Jeannie is not interested in listening.
Back in the living room, Whitey tells Lennie how the merchant marines are changing, how men who used to stick up for each other now turn their backs. How the old generation of sailors are dwindling, most of them alcoholics like Whitey. Whitey speaks of his overwhelming memories - of jails and brothels and bars and docks. When Lennie tries to express his concern, Whitey tells him to "shove it" (36).
In a section written in italics, Whitey reflects on his past with Helen and Lennie. He had once meant so much to them: a "tie to adventure" for Lennie, a sympathetic ear for Helen's struggles, a good friend to both. Though they once "believed in his salvation" if he could get away from the difficulties of his merchant marine life, they now know he is too far gone, his "decaying body...betraying him" (37).
Helen expresses her concern, but he rejects their pity and judgment. As he takes another drink, he leaves their house, perhaps for good.
Implicitly set in the 1950s, "Hey Sailor, What Ship?" grapples with many of the cultural concerns of the time, including those over the nuclear family. The family we see in the story could be simply an American stereotype - the working father, the home-bound mother, and three lovely daughters. Yet Helen and Lennie's family complicates this stereotype. In her innovative and overwhelming dialogue style, Tillie Olsen gives the family not a simple, over-arching patriarchal voice, but instead many, equally-weighted ones across age and gender. Through each vocalized character, the reader gets a different image of Whitey and their lives.
The free-wheeling narrative style allows Olsen to jump between several different perspectives within the third-person point of view. Though Whitey is ostensibly the main character - evident from the fact that the italics are most clearly aligned with his perspective - each character controls the perspective throughout. For instance, Allie's worldview is naive, while Jeannie's is peer-pressured and jaded.
What comes across through these myriad perspectives is that each member of the family is recognizing the permeability of the family unit through their views on Whitey. Obviously, he is somewhat of a disaster, but they all know in their own ways that he is important to them. In other words, they are not a self-sufficient and perfect unit - as cultural values might suggest - but instead a complicated construction of individuals and relationships that change and grow.
Another reflected cultural concern from the time is the presence of cultural and ideological conformity, something that Whitey threatens through his international exposure and alternative lifestyle. The narrative makes many references to Whitey's political activism - he and Lennie had participated in a 1934 strike; he is the "ship's delegate" to a union; and he recalls defending a man who deserved overtime pay. In the 1950s, the McCarthyism era, such progressive outlooks were considered dangerous, and so is Whitey somewhat dangerous to the values that the family implicitly represents. When Whitey mourns the loss of the sailor brotherhood in the story's final section, he is mourning not only his particular losses, but moreover an era that is more and more concerned with conformity.
This political background distinguishes what might otherwise be simply a stereotypical drunken sailor story. Our first depiction of Whitey is through an almost theatrical portrayal of drunkenness - confusion, missing money, mixed-up names and places. As we explore Whitey's connection to the family, however, a more complex picture emerges. Whitey is both a political activist with a "tough mind," one who brings Lennie news of the wider world, and also a helping and empathetic friend to Helen. He is not an exaggerated masculine figure, but rather one who seeks to understand both the man and woman in the family. Especially through his relationship to Helen, Whitey complicates traditional masculinity, by helping her clean the house and take care of her children. Whereas a sailor like Whitey might otherwise fade into obscurity, unknown and limited by stereotypes, Olsen's portrayal breathes life into him, giving him a voice to compete with that of the nuclear family.
This complexity places Whitey at the intersection of the public and private spheres. Whereas the family could represent only the private sphere, Whitey's interludes in their life bring an awareness of the wider world, of poor, lost children in Manilla, and of union activities and political struggle. The family also enables the reader to look at Whitey's private life, to try to piece together the complex experiences that transformed a proud, young seafaring man into the battered and drunken sailor. He gains an interiority beyond his drunken thoughts, showing his desire for children and stable relationships.
And of course, Olsen makes this point clear through the use of italics in her narrative. Because the story is not first-person, these internal interludes have a disorienting effect, as though suggesting that Whitey is somewhat alienated from himself. He is watching and trying to understand himself, unable to quite grasp his own identity. All of the complexities discussed above are implied through this structure, and help to understand how he can lose track of even his own name. Obviously, this disconnected narrative is largely a representation of an alcoholic mind, but it has a larger resonance when understood as the voice of an individual who has no defined place in an ever-homogenized society.
Perhaps the most emblematic element of this disconnected narrative style - Whitey's catchphrase, "Hey sailor, what ship?" - is also its most thematically resonant. The phrase works to communicate all these struggles, as well as the pervading feeling of loss that shaped this historical period. Used to ask a sailor where he is going and what ship he is taking there, the question also asks more widely where any individual is going, and where society is going as well. Where are the old, political seamen like Whitey going? Where has their communal brotherhood gone? What is the fate of the family? "Hey Sailor, What Ship?" cannot answer these questions completely, but it forces the reader to consider them through the stirring and complex portrait of the marginalized figures within society.