Mulligan repeats, to Stephen, a fellow medical student's surmise that Stephen has "g. p. i.," or "General paralysis of the insane"—an outdated medical term for tertiary syphilis, syphilis of the central nervous system. The insult may not be quite as insensitive as it first appears, but it also seems to have acquired a sharper edge retrospectively from the medical problems that later appeared in Joyce's family.

General paresis, or general paralysis of the insane, or paralytic dementia, was a severe affliction of the brain first diagnosed in the early 19th century and originally attributed to moral failings. In the 1880s physicians established a link to syphilis (a biological cause, but certainly involving moral failings!), and in the 20th century various medicines, culminating in penicillin, were found effective in treating the condition. Before that, g.p.i. had a 100% fatality rate, and it filled countless beds in psychiatric hospitals.

Gifford observes that medical students sometimes used the term as joking slang for mere eccentricity, and Slote cites Eric Partridge's Dictionary of Slang to that effect. Arguments have been made, however—notably by Kathleen Ferris—that Joyce did suffer from advanced syphilis. The mental illness of his daughter Lucia was reportedly diagnosed as schizophrenia in the 1930s, and Ferris acknowledges that that condition could account for some of her symptoms. But syphilitic paresis accounts for more, she suggests, and can be caused by spirochetes transmitted in utero (106-11). Lucia once told her father “that she had syphilis” (111). Ferris sees the evidence of this disease in Joyce's fictional offspring as well: Stephen and Bloom, she argues, between them display an assortment of symptoms (stiff walk, bad eyesight, digestive problems, hallucinations) that might be caused by syphilis.

Syphilis aside, Joyce’s works contain a number of instances of mental imbalance. The mother in Eveline (a story in Dubliners) lived a “life of commonplace sacrifices closing in final craziness,” and the old man in An Encounter seems deeply disturbed. Walking down a lane in A Portrait, Stephen hears “a mad nun screeching in the nuns’ madhouse beyond the wall.  — Jesus! O Jesus! Jesus!” Ulysses introduces two disturbed individuals in Lestrygonians: Dennis Breen, and Cashel Boyle O’Connor Fitzmaurice Tisdall Farrell. When Bloom points out the “dotty” Farrell to Breen’s wife, she replies, “Denis will be like that one of these days.” Haines, with his predatory nightmares and itchy trigger finger, is "A woful lunatic!" Even the even-tempered Bloom fears slipping into insanity, perhaps because of his father's suicide. In Ithaca, we learn that he fears "The committal of homicide or suicide during sleep by an aberration of the light of reason."

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