Associated with the Chicago School and known for his role in designing the first modern skyscrapers. He co-founded the firm, Holabird & Roche, with fellow architect Martin Roche in 1883. Among their most famous designs were the Gage Building and the Marquette Building.
He spent a portion of his educational career at the United States Military Academy at West Point before resigning and relocating to Chicago. He was then hired by the architectural firm of William Le Baron Jenney, where he collaborated with the famed O.C. Simonds.
He created the "Chicago window," an architectural innovation involving seemingly all-glass building facades.
He was the uncle of nurse Agnes von Kurowsky, who was the inspiration for the character, Catherine Barkley, in 'A Farewell to Arms' by
He and Louis Sullivan were both founding architects of the Chicago School.