During the interwar years, John Masefield wrote three novels featuring a male protagonist with the surname “Harker” struggling against an adversary called Abner Brown. The first of these novels was written for an adult audience, the remaining two for children. The chronological sequence of these three novels and the relationship between their characters is far from clear, although the recurrence of names and places gives the impression that they should be read in connection with one another. In the present study, I will argue that the trilogy, whose settings correspond to specific periods of the author’s own life, can be read as a tripartite reflection on childhood, loss and the redeeming power of art.