The triple of houses on Chicago Avenue, just west of Wright's Home & Studio, stand out for their transitional nature from the rest of Wright's later designs. They have come to be called the Bootleg Houses as they were designed by Wright while he was still working at the firm of Adler & Sullivan, who forbade him to take outside commissions, hence their "bootleg" appelation.
Wright's design for these houses, especially the nearly identical Thomas H. Gale and Robert P. Parker Houses, were derived from the more expensive residence he had designed earlier in 1892 for Robert Emmond of LaGrange, Illinois. They were built later that same year by realtor Thomas Gale, who sold the house pictured at left to attorney Robert Parker.
In spite of their small size and inexpensive detailing, the Gale and Parker Houses are of interest for what they reveal about Wright's development as an architect.
Their irregular composition, consisting of octagonal bays joined to a rectangular core, the whole covered by high-pitched roofs with polygonal dormers, reflect the style of design of Wright's first teacher, Joseph Silsbee. The influence of Louis Sullivan, especially his philosophy of "geometric simplification", is seen in the taut masses of these houses, made clear when contrasted with the more ample rounded forms of true Queen Anne designs so popular at that time.