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Harry Smith would talk at great length and in extraordinary depth on topics spanning many subjects and ranges of knowledge. According to Khem Caigan, a typical chain of free association might range from, for example, the macrocosm and the microcosm and the great chain of being to bioelectromagnetics and electrophysiology and the geomagnetic field and the psyche, Sylvanus Thompson and Max Knoll and the generation of phosphenes, musicology and molecular physics, parapsychology and poltergeist phenomena; the Margery and Helene Smith mediumship cases, the tarot and the Key of Solomon the King, Harold Scott MacDonald Coxeter’s Regular Polytopes and the Leech Lattice, his collection of 30,000 Ukrainian Easter eggs and Seminole quilts; alchemy and the Philosopher’s Stone; all in an effort to demonstrate the underlying connectedness and interrelatedness of all things for his audience of the moment. On occasion, the less astute of his listeners would have trouble following his train of thought, as one subject always led on to another.

Harry often had difficulty paying his bills and had very little interest in maintaining a normal, ordered life. He would frequently borrow money which would never be paid back, money that he would often spend on records and books, even when low on essential items (such as food). On the other hand, Khem Caigan is quick to point out that Harry was generous to a fault, always springing for a much appreciated meal when he was down on his luck. It is suggested that Harry enjoyed alcohol, cannabis, Dexedrine, Dewamesk, hashish, LSD, mescaline, peyote, psilocybin, and other entheogens on occasion.