Raised as a gentleman's son, Redburn—like Melville—experienced the financial failure and death of his businessman father, and went to sea determined to make something of himself. Redburn is aided by his brother's friend, Mr. Jones, whose unfortunate representation of the boy to Captain Riga as a person of means results in his being denied a much-needed advance on his wages. Thus he boards ship without the necessities, wearing torn and inappropriate clothes that make him the object of the crew's ridicule. His behavior is likewise inappropriate, as he attempts to make a social call upon the captain in his cabin—as one gentleman to another. Redburn's first days on board ship consist of a series of unfortunate incidents designed to show the boy as a friendless outcast, ill-suited to the hard labor of a sailor, but at the same time lacking the means to be a gentleman. While the crew of the Highlander treats Redburn cruelly, it is only their leader, Jackson, who is truly depraved and evil.
Once in Liverpool, Redburn attempts to retrace the footsteps of his father. Disillusioned, the boy becomes despondent as a result of his encounters with poverty, debauchery, and crime throughout Liverpool. Redburn eventually meets Harry Bolton. They return to Liverpool in time to find the Highlander about to embark on the return trip to America. Bolton, having gambled away his money, signs on for the return trip as a common seaman.