Olmstead's history is defective for some years after he left Kankakee. In October, 1892, we hear of him as a letter-carrier in Chicago. During the following summer he developed a passion for William Clifford, a fellow letter-carrier about his own age, also previously a schoolteacher, and regarded as one of the most reliable and efficient men in the service. For a time Clifford seems to have shared this passion, or to have submitted to it, but he quickly ended the relationship and urged his friend to undergo medical treatment, offering to pay the expenses himself. Olmstead continued to write letters of the most passionate description to Clifford, and followed him about constantly until the latter's life was made miserable. In December, 1893, Clifford placed the letters in the postmaster's hands, and Olmstead was requested to resign at once. Olmstead complained to the Civil Service Commission at Washington that he had been dismissed without cause, and also applied for reinstatement, but without success. In the meanwhile, apparently on the advice of friends, he went into hospital, and in the middle of February, 1894, his testicles were removed. No report from the hospital is to hand. The effect of removing the testicles was far from beneficial, and he began to suffer from hysterical melancholia. A little later he went into hospital again. On March 19th he wrote to Dr. Talbot from the Mercy Hospital, Chicago: "I returned to Chicago last Wednesday night, but felt so miserable I concluded to enter a hospital again, and so came to Mercy, which is very good as hospitals go. But I might as well go to Hades as far as any hope of my getting well is concerned. I am utterly incorrigible, utterly incurable, and utterly impossible. At home I thought for a time that I was cured, but I was mistaken, and after seeing Clifford last Thursday I have grown worse than ever so far as my passion for him is concerned. Heaven, only knows how hard I have tried to make a decent creature out of myself, but my vileness is uncontrollable, and I might as well give up and die. I wonder if the doctors knew that after emasculation it was possible for a man to have erections, commit masturbation, and have the same passion as before. I am ashamed of myself; I hate myself; but I can't help it. I have friends among nice people, play the piano, love music, books, and everything that is beautiful and elevating; yet they can't elevate me, because this load of inborn vileness drags me down and prevents my perfect enjoyment of anything. Doctors are the only ones who understand and know my helplessness before this monster. I think and work till my brain whirls, and I can scarce refrain from crying out my troubles." This letter was written a few days before the crime was committed.