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John Simson Woolson (December 6, 1840 – December 4, 1899) was a federal judge in the United States District Court for the Southern District of Iowa in the late Nineteenth century.
Born in Tonawanda, New York, Woolson received an A.B. (1860) and an A.M. (1863) from Wesleyan University. Interrupting his legal education to serve in the Civil War, he was an assistant paymaster in the United States Navy from 1862 to 1865. Following the war, he relocated to Iowa, where he read law to enter the bar in 1866. He was in private practice in Mt. Pleasant, Iowa from 1866 to 1891. While in practice, he served as a member of the Iowa State Senate from 1876 to 1881, and from 1885 to 1891.
On August 14, 1891, after the death of Judge James M. Love of the Southern District of Iowa, President Benjamin Harrison gave Woolson a recess appointment to fill the vacancy. Formally nominated on December 10, 1891, Woolson was confirmed by the United States Senate on January 11, 1892, and received his commission the same day. Woolson served until his death in Des Moines, Iowa, on December 4, 1899.