After university, Holmes relocated to Chicago to pursue a career in Pharmaceuticals. While there, he also engaged in many unethical business, real estate, and promotional deals, under the name of H.H. Holmes.
Holmes lived in Chicago, but his wife and son still lived back in New Hampshire. While he was still married, Holmes met and married Myrta Belknap in Chicago on January 28, 1887, and had a daughter, Lucy, in July of 1889. He lived with Myrta and Lucy in Wilmette, Illinois, and spent most of his time in Chicago tending to business. He filed for divorce from Clara after marrying Myrta, but the divorce was never finalized.
In January of 1894, Holmes also married Georgiana Yoke in Denver, Colorado, while still married to Myrta and Clara. Moreover, while married to the three of them, he also had an affair with Julia Smythe, the wife of one of his previous employees. She would later become one of Holmes' victims. To make a count, Holmes, at that point, had three wives and one girlfriend.
Murders
In the summer of 1886, Holmes came across Dr. E. S. Holton's Drugstore at the corner of S. Wallace and W. 63rd Street, in the neighborhood of Englewood. Dr. Holton’s wife took care of the store while he was ailing from cancer. Weighed down by personal distress and the responsibility of managing a business, Mrs. Holton gave Holmes a job. Holmes proved himself an astute employee and when Dr. Holton passed away, Holmes used his well-honed charisma to console the grieving widow. Consequently, he convinced Mrs. Holton that selling the drugstore to him would alleviate the burden of her responsibilities. Holmes’ proposal seemed like a godsend to the elderly woman and she agreed. Holmes purchased the store from her primarily with funds acquired by mortgaging the store’s fixtures and inventory, the loan to be repaid in generous monthly installments of one hundred dollars, which would equate to about $3000.00 per month today. However, Mrs. Holton disappeared mysteriously not long after Dr. Holton died. Holmes told people she was visiting relatives out in California. As people began asking after her return, he told them that she was enjoying California so much that she had decided to live there.
Dr. Holmes procured a parcel of land across from the drugstore where he built a three-story, block-long building that the neighborhood referred to as the Castle. It was opened as a hotel for the World's Columbian Exposition in 1893. Part of the formation was used as commercial space while the ground floor contained Holmes's own relocated Drugstore, as well as assorted shops. The upper two floors contained his personal office and over 100 windowless rooms with doorways opening onto to brick walls, abnormally angled hallways, stairways to nowhere, doors only operable from the outside, and a multitude of other bizarre and convoluted designs. Holmes frequently altered the plans during the construction phase of the Castle so that only he fully understood the layout of the building. Thus, the possibility of being reported to the police as suspicious was lessened.
After the completion of the hotel, Holmes required women who wanted to work for him to take out life insurance policies as a stipulation of being hired. Holmes would pay the premiums, but would also be the beneficiary. He tortured and killed some of his victims; others, he locked some in a soundproof bedroom fitted with gas lines that let him asphyxiate them at anytime; and some were locked in a huge soundproof bank vault near his office where they were left to suffocate. The victims' bodies were dropped down a secret chute to the basement where many were carefully dissected, stripped of their flesh, crafted into skeleton models, and sold to medical schools. Holmes cremated the bodies, or placed them in lime pits for obliteration. He had two massive furnaces, pits of acid, bottles of assorted poisons, and even a stretching rack. Through the many connections he had gained in medical school, he sold the skeletons and organs of his victims with little difficulty.
Schemes, Murders
Subsequent to the World's Fair in 1893, with creditors closing in and the economy in a general slump, Holmes skipped out of Chicago to avoid his debt. He reemerged in Fort Worth, Texas, where he had inherited property from two railroad heiress sisters. He promised to marry one of them, and then murdered them both. While in Texas, Holmes sought to construct another Castle along the same lines of his Chicago business. He soon abandoned this venture, however, finding the law enforcement climate in Texas unwelcoming.
Holmes continued to travel about the United States and Canada, and while it seems probable that he continued to kill, the only murders around him that can be confirmed during this period are those of his longtime associate, Benjamin Pitezel, and three of Pitezel’s children, Alice, Nellie, and Howard.
In July of 1894, Holmes was detained and temporarily incarcerated for the first time for a charge related to horse fraud in St. Louis. He was swiftly bailed out; however, while in jail, he spoke with convicted train robber, Marion Hedgepeth who was serving a twenty-five year sentence. Holmes had invented a plan to deceive an insurance company out of $10,000 by taking out a policy on himself and then faking his own death. Holmes promised to pay Hedgepeth a $500.00 fee in exchange for the name of a lawyer who could be trusted. He was directed to Colonel Jeptha Howe, the brother of a public defender, who commended Holmes’s scheme. Holmes's plan to sham his own death failed, however, when the insurance company became apprehensive and refused to pay. Holmes did not press his claim. He instead concocted a comparable plan with his associate, Benjamin Pitezel, a carpenter with a criminal past who Holmes met during construction of the Castle in 1889.
Pitezel had arranged to fake his own death so that his wife could collect on the $10,000 policy which she was to divide with Holmes and the shady attorney, Howe. The scheme was to take place in Philadelphia. Pitezel would set himself up as an inventor under the name B. F. Perry, and then be killed and disfigured in a lab explosion. Holmes was to find a suitable corpse to play the role of Pitezel. Of course, Holmes killed Pitezel instead. Forensic evidence offered at Holmes's later trial indicated that chloroform was used in Pitezel's death, seemingly to fake suicide (Pitezel had been an alcoholic and chronic depressive). Using Pitezel’s genuine corpse, Holmes collected on the insurance policy. He then coerced Pitezel's wife into allowing three of her five children Nellie, Alice, and Howard, to stay in his custody. The eldest daughter and baby remained with Mrs. Pitezel.
Holmes travelled with the children through the northern United States and into Canada – Mrs. Pitezal travelled along an alternate route – all the while using a mixture of aliases and lying to Mrs. Pitezel concerning her husband's death, claiming that Pitezel was in hiding in South America. A Philadelphia detective by the name of Frank Geyer tracked Holmes, and found the decomposed bodies of two of the Pitezel girls in Toronto, Canada. He then followed Holmes to Indianapolis where Holmes had rented a cottage and was reported to have visited a local pharmacy to purchase drugs to kill young Howard Pitezel, and a repair shop to sharpen the knives he used to dismember the boy’s body before he burned it. The boy's teeth and bits of bone were later discovered in the home's chimney. In 1894, Marion Hedgepeth, Holmes’s former jail mate, tipped off the police because Holmes had neglected to pay him off as promised for his help.
Arrest