The years 1984 and 1985 constitute the centennial of one of the 19th century's most significant structures, the Home Insurance Building in Chicago. Ground for the Home Insurance was broken 1 May 1884 and it received its first tenants in the fall of 1885. Since that time, some have hailed it as the world's first true skyscraper; others have seen it as unspectacular and merely transitional. This paper will explore the opinions of the men who were most intimately connected with its construction: the architect, William Le Baron Jenney; his partner, William Mundie; the building's fireproofing contractor, Peter B. Wight; and one of Jenney's competitors for the commission, Frederick Baumann. I have based this article on documents, some of them recently discovered, that were written at widely different times. When brought together, however, they seem to create a dialog between these men, the results of which cast some light on the circumstances surrounding the design and erection of the Home Insurance Building. Moreover, these documents give us valuable insight into the human aspects of what has heretofore been held as a purely technical problem in the history of architecture.