Friendship Between Daniel Upton and Edward Derby

The friendship between Daniel Upton and Edward Pickman Derby is the human bond at the center of the story’s escalating horror: it begins in childhood as a kinship of imagination and becomes, in adulthood, Derby’s chief source of advice and shelter. Upton’s long familiarity with Derby gives him reasons to recognize changes in his friend, but it does not spare him from uncertainty when those changes become impossible to explain. In the end, friendship demands an act Upton understands as both rescue and violence: he kills the figure he believes is no longer Edward Pickman Derby.

Childhood and Shared Imagination

Upton says he has known Edward Pickman Derby all his life. Eight years older, he was sixteen when Derby was eight, and the younger boy’s precocious learning gave them common ground despite the age difference. Derby had begun writing sombre, fantastic verse at seven. His parents’ close supervision, prompted by his physical weaknesses, restricted his independence and opportunities to play with other children; imaginative writing became an important avenue of freedom. Upton, then drawn to grotesque art, found a rare kindred spirit in the boy’s work and sensibility.

Their friendship was shaped by Arkham as well as by their private tastes. Upton connects their shared attraction to shadows and marvels with the town’s old, decaying streets and its legends. The relationship was not merely an older man’s admiration for a gifted child: as Derby’s talent developed, Upton considered illustrating his poems, and, although he later turned to architecture instead, the companionship endured. In Derby’s eighteenth year, his collection of nightmare-like poems appeared as Azathoth and Other Horrors and caused a literary sensation. The achievement confirmed the seriousness of the talent that had first drawn Upton to him.

An Adult Confidant

As adults, the friends retained a closeness that was unusual in Derby’s sheltered life. Upton studied at Harvard, worked in a Boston architect’s office, married, and returned to Arkham to practise architecture. Derby, meanwhile, remained dependent on his parents and socially withdrawn. He attended Miskatonic University while living at home, then became absorbed in obscure magical writings held in its library. Upton knew of Derby’s intense intellectual interests, including his reading in forbidden occult lore, even though Derby concealed that reading from his parents.

Upton’s home became one of the steady places in Derby’s routine. Derby called almost every evening, and his customary knock—three brisk strokes followed after a pause by two more—became familiar enough for Upton to recognize it as a personal signal. Upton also visited Derby’s home and took an envious interest in the growing library. These habits made the friendship part of everyday life: its intimacy was carried not only by intellectual conversation but by repeated visits and a recognizable sound at the door.

By twenty-five, Derby was learned and a fairly well-known poet and fantasist, but his lack of experience and practical responsibility had limited his development. Upton describes himself as perhaps Derby’s closest friend and as an inexhaustible source of theoretical conversation. Derby, in turn, relied on Upton for advice about matters he did not wish to take to his parents. That reliance could have material consequences: after Derby became involved in a wild college gathering, he borrowed money from Upton to pay blackmail and keep his presence from his father. Upton’s support thus extended beyond literary fellowship, although it did not make Derby independent.

Loyalty Under Strain

Their differing circumstances did not end the attachment. During the war, Derby stayed home because of his health and ingrained timidity; Upton went to Plattsburg for a commission but did not serve overseas. Later, when Derby’s mother died, he suffered an unusual psychological collapse. His father took him to Europe, and Derby recovered without visible effects. Upton records these changes as part of a friendship sustained across years, even as Derby’s dependence and private distress remained persistent concerns.

The sharpest test comes after Derby has been away in Maine. A telegram from the marshal at Chesuncook reports that a disoriented man has emerged from the woods asking for Upton’s protection. Upton makes the difficult journey and finds Derby in a cell, fluctuating between agitation and passivity. Derby recounts an occult ordeal in fragments, including being taken against his will to a ritual place and seeing a changing creature. Upton cannot accept the account as literal truth at first, but he does not abandon his friend. He calms him, obtains decent clothes, and drives him back toward Arkham rather than returning him to his wife, Asenath Waite. Believing that Derby may have undergone a real hypnotic ordeal even if his explanations are delusional, Upton resolves to house him and later help him seek a divorce.

That response shows the balance at the heart of their friendship: Upton doubts Derby’s interpretation while treating his distress as real. When Derby later argues that Asenath Waite is actually Ephraim Waite and that a ritual at Hallowmass would make a body exchange permanent, Upton recognizes his friend’s terror but still considers the story a possible case for institutional care. He nevertheless refuses to send Derby to an asylum and hopes that safety and distance from Asenath Waite will help. Loyalty does not immediately become belief; it first takes the form of protection and a willingness to keep listening.

The Final Obligation

The relationship changes when Upton receives Derby’s last warning. The note says that Derby killed Asenath Waite, concealed her body, and later found himself trapped in it as her spirit took possession of his own body. He claims that the figure held at the Arkham Sanitarium is no longer Edward Pickman Derby, and asks Upton to kill it and ensure that it is cremated. Upton cannot verify every part of this account, but he later says he believes what Derby told him. His understanding of their friendship has become inseparable from the question of whether the person before him is still his friend.

After the visitor from the sanitarium reaches Upton’s home and leaves the written warning, Upton goes to the institution the next day and shoots the person held there. He describes the act as being for Derby’s sake and for the world’s, while remaining afraid that the powers involved may survive physical death. His insistence on cremation and his fear that he could be the next victim reveal the cost of the decision: he acts from loyalty, but cannot obtain certainty or peace from it. The friendship that began in shared poems and nightly visits ends in Upton’s attempt to defend Derby’s identity after he believes Derby can no longer defend it himself.