By 1886, Holmes runs a highly successful business at his pharmacy in Englewood. He begins to court a woman he met in Minneapolis named Myrta. Myrta is impressed with Holmes’s dashing manner, and the exciting city he now lives in. Holmes breaks all the rules of courtship, but when he proposes to Myrta, she eagerly accepts. Holmes files a petition to divorce his current wife, Clara, accusing her of infidelity, an extremely serious charge at the time, though his petition for divorce is eventually dismissed. He thinks to himself that young women are weak and naïve. Within two years of marriage, Myrta is pregnant.
Holmes affects a manner of kindness and attractiveness, but secretly finds Myrta, and all women, pathetic. He is aggressive as well as dishonest; he doesn’t just divorce his first wife, he accuses her of wrongdoing, seemingly without any grounds. Yet Myrta knows none of this — she seems to think of Holmes as an extension of the city he lives in: exciting, unpredictable, a little dangerous, but irresistible.
Myrta is impressed with the energy of Chicago, and at first she adores Holmes for his gentle manner and ambition to succeed. But she quickly becomes jealous of his flirtatious behavior around female customers. She writes to her parents about her sadness, and they move to Illinois. Myrta joins her parents, and there gives birth to her child with Holmes, named Lucy. Holmes visits Myrta there, and charms her parents. Myrta says that Lucy responds well to Holmes, which makes Myrta trust him more.
Holmes’s appearances can only convince for so long. Unfortunately, women only seem to notice that he is a liar after they have already committed to him. By the time Myrta starts to become jealous, she is carrying Holmes’s child. It may also be that Holmes stops trying to charm Myrta after they’re married, not that she finally sees through him.
In 1888, Holmes buys land across the street from his pharmacy under a false name. He begins designing a building with stores on the ground floor and lodgings on floors two and three, along with gas jets and a secret basement. He is aroused by the thought of women living there.
Holmes finally shows feelings of attraction, but they’re not attraction to any typical thing; instead, he is aroused by the sense of control he wields over other, defenseless people.
Holmes hires workers to build, deliberately overworking them and encouraging them to leave early on. In this way, no one but Holmes knows the plans of the entire building, or questions unusual features, like open gas nozzles in vaults. He asks one worker to drop a brick on Holmes’s “brother in law,” possibly because he wants to know if the worker is trustworthy. Holmes finds three trustworthy workers: Charles Chappell, Patrick Quinlan, and most importantly, Benjamin Pitezal, a tall, skeletal man who a lawyer will later describe as Holmes’s puppet.
By hiring workers for his new building, Holmes is holding “tryouts” for henchmen and helpers. In part, his building is terrifying because only he knows all of its secrets — none of the workers stays around long enough to understand more than a few rooms.
In 1888, Jack the Ripper commits his first murders, brutally stabbing prostitutes. These events fascinate everyone in Chicago, but especially Holmes.
It’s unclear why Jack the Ripper is so fascinating to Chicago. For Holmes, it’s because he identifies with the serial killer, and enjoys hurting others. But for most of Chicago, it’s in part because they don’t think a serial killer could ever come to the United States. For most people, it’s titillating but safe entertainment, the equivalent of a horror movie.
By June 1889, Chicago officially incorporates Englewood into its city limits, and a new police precinct opens in the area, near Holmes’s building. Holmes sells his old drugstore and promptly opens a new one across the street, even though he has assured his buyer that he’ll face little competition. Holmes falls into debt to finance his projects, but he is able to pass his debts on to H.S. Campbell, one of his aliases.
Holmes lies freely and easily to others, first telling his buyer that he’ll have no competition and then going directly into competition with him. Even when it comes to money — one of the simplest ways that society limits what people can do — Holmes manages to spend far more than he has by pretending to be someone else, Campbell.
Holmes buys chloroform, at first insisting that he is using it for scientific experiments, then denying this. He convinces a woman named Strowers to take out a life insurance policy with Holmes as the beneficiary. Holmes pays her 6,000 dollars to do so, and tells her not to be afraid of him — this, of course, terrifies her.
Paradoxically, saying, “Don’t be afraid of me” is one of the scariest things one could hear. In part, Holmes may be toying with Strowers, knowing full well that she will be terrified. It’s a bigger mystery why a women would write a life insurance policy for another man — perhaps she implicitly trusts Holmes, and perhaps people were simply more trusting a hundred years ago.
Holmes hears about the upcoming World’s Fair in Jackson Park, and plans to exploit it for his own ends.
Holmes’s connection to the WF is clear: he will exploit people’s desire for entertainment. Larson doesn’t explain exactly how, which make Holmes’s plan seem even more sinister.