referred to his “American-born parents”. O'Malley claimed to have a brother and sister, and apparently stayed with his brother Walter in the small community of Kelly, Kansas, when he returned to the U.S. in 1917. Childhood O'Malley grew up in Kansas, possibly in Pawnee County. He most likely had little formal education, as his writing was "usually deficient in style, grammar and spelling". According to O'Malley's own account, his father was killed in the American Civil War when he was a young boy. He was then sent to live in New York City with his aunt and uncle, Edward and Caroline O'Malley, where his uncle ran a small bank near Wall Street. He began working there at the age of 14, and was promoted to teller at 16 and handling loans by 19. After a disagreement with his uncle, he left the bank at the age of 22 and took a job selling insurance. regards the basic facts of O'Malley's account to be accurate, as he had a detailed knowledge of American banking practices and of New York City. However, he expresses doubt over the details. describes it as "at least partially true", but notes "there is no evidence to suggest that he ever lived in New York". Adult life in the United States Before he moved to Australia, O'Malley lived a transient lifestyle as an insurance salesman and real estate agent on the west coast of the United States. There are contemporary references to him in California, Oregon, and Washington Territory, as well as in his presumptive home state of Kansas. At various times, O'Malley sold policies for the Northwestern Mutual Life Insurance Company, the Home Life Insurance Company of New York, and the Equitable Life Insurance Company. In April 1887, the Chicago Inter Ocean reported that he had forwarded policies amounting to $200,000 from Oregon, an immense sum at the time. He may have also made money engaging in land speculation, as he was wealthy enough to invest in property in Seattle which he retained for several decades. Surviving records indicate that he had "somewhat dubious" business practices – in 1887, he made a series of large deposits at a bank in Corvallis, Oregon, then abruptly withdrew his entire account. As a young man, O'Malley became a devotee of the temperance movement; his apparent home state of Kansas had been one of the first to enact statewide prohibition.