He read law in Rochester, NY, and eventually moved to Kalamazoo. He served in private practice until April 1883 when he ran for the remainder of Isaac Marston’s term, as a candidate of the combined Democratic and Greenback Parties. His victory, and that of John Champlin, were shocking as they represented the first Republican losses in a statewide election since 1856.
Sherwood’s term on the Michigan Supreme Court overlapped with Big Four Justices Thomas M. Cooley and James V. Campbell. One of the notable opinions in which he was involved was the famous cow case Sherwood v Walker (although the Sherwood in that case was no relation to the Justice).
Sherwood was defeated by Republican and Civil War veteran Claudius Grant in 1889. He returned to his law practice and died on March 28, 1896, in Chicago, Illinois.