Chattanooga businesswoman Harriet Whiteside was born May 3, 1824, in Wytheville, Virginia, and educated at the Moravian School in Winston-Salem, North Carolina, to be a teacher. At the age of nineteen she arrived in Chattanooga to teach music to one of the five children of Colonel James A. Whiteside, a forty-year-old widower and Chattanooga’s leading businessman, whom she married on February 1, 1844. A woman of strong intellectual interests, Whiteside ably supported her husband in his many ventures in addition to bearing nine children between 1845 and 1859. When he died in 1861, Colonel Whiteside left a fortune under the control of his widow.
Whiteside acted decisively, selling what she could to pay debt against the estate with Confederate dollars. She also used Confederate money to buy tobacco that a Union friend sold in the east for greenbacks. She scarcely had time to put her husband’s affairs in order before Confederate refugees began pouring into Chattanooga, followed in September 1863, by Union troops who remained in the city for the duration of the war. Whiteside, an ardent secessionist like her husband, was among those Confederate sympathizers deported to the North.
During her absence, many of her papers were lost, and when she returned to Chattanooga, she had to fight to reestablish ownership and control of her late husband’s estate. Later efforts to combat a rival turnpike company on Lookout Mountain and to control access to the Point, a fracas popularly known as the “War of the Mountain Roads,” earned her some public notoriety, as did her divorce suit against a second husband, Varney A. Gaskill.
At the time of her death on February 1, 1903, some Chattanoogans breathed a sigh of relief because of the controversy she had engendered for the past forty years. But one of her former attorneys, W. G. M. Thomas praised her as “an exceedingly superior woman” and “the best informed woman” of any of his clients. He also characterized her as “the best business woman I ever knew.” (1)