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Holmes has a quite a bit of money. Nobody is quite sure where all it has come from but it is certainly there. He starts off his entrepreneurship by buying and opening a pharmacy under a fake name. He eventually cells this pharmacy and starts work on a hotel, as the world fair is coming to town soon. He uses this hotel as a way of trapping his victims. It has many secrets and rooms for dark uses. He makes sure to also use a fake name for this project. As well as firing workers after a couple months. As he doesn't want to keep anybody around for too long. Lest they learn his secrets.
Holmes is a sociopath. He feels no human emotion and is incapable of sympathy. He gets sexual pleasure from seeing vulnerable women struggle. So he infiltrates their lives and acts as a love interest. Once the woman has fallen for him, he finds an elaborate way to kill them. He sees these women only as assets, to give him pleasure. Through out the story he goes through many women. Such as Belknap, Cigrand, and the williams sisters.
Holmes´s is in love with himself. It seems he is the only human he can care about. And so he is very narcissistic. This ends up being his downfall in the end, however. He always wants a challenge. A man like Holmes is too prideful to take the easy way out. So when the debtors come asking for money, even though he has the funds to pay, he still tries to sway them with his cunning personality. He falls short though, and his whole scheme is ruined.
As previously stated, Holmes feels no sympathy. He sees people as assets and nothing else. He does not value human life, except for his own. He not only manipulates women, but also his workers. He wants power and conquest. He will do anything to reach those goals and feels no pity. He uses what we would call gas-lighting today.
Holmes is one of the main antagonists in the story. His schemes make the world fair plans go slower, and worsens the integrity of the event. He is meant to represent the evil and dark history of the city of Chicago, and world fair. He personifies the fair. On the outside he appears charming and kind however we know that there is darkness behind his smile. He represents the hardships, betrayals and deaths that were needed to make the world fair happen.