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 The postcard was published by the E.C. Kropp Company of Milwaukee, Wisconsin. It was probably made before the building was constructed, which was in 1910. The Woodruff was one of three new Springfield buildings opened to the public with much fanfare on February 1, 1911, the other two being the Republican Building and the Frisco Building.

The Woodruff Building sits on the northwest corner of St. Louis Street and Jefferson Avenue on the east side of the Square. It was owned by, and named for, Springfield attorney and investor John T. Woodruff. The ten-story office building contained a drugstore, barber shop, pool hall and two elevators. Since this was Springfield's first skyscraper, a light-hearted newspaper piece from 1910 tells of the danger of people's hats falling off their heads when they look up at the tall building.

In 1929, John T. Woodruff sold the building to F.X. Heer for $700,000. In 1959 the Woodruff building was expanded, adding 23,000 additional square feet to what was already Springfield's largest office building. The cost was estimated at $650,000. In August of 1994 Warren Davis, a Bolivar businessman purchased the building from the Heer-Andres Company for an undisclosed amount. Through the years the building has been a popular office choice for lawyers because the Missouri Court of Appeals was located there.

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