Political Career
Willson's political career began when was he appointed chief clerk of the U.S. Treasury Department under Benjamin Bristow. He served in this capacity from December 1875 to August 1876, resigning to continue his law practice in Louisville. On July 23, 1877, Willson married Mary Elizabeth Ekin; their only child died as an infant.
A Republican in a predominantly Democratic state, Willson suffered several defeats in his canvasses for public office. His 1879 loss in an election for a seat in the Kentucky Senate marked the first in a string of political defeats. He failed in bids to represent Kentucky's Fifth District in the U.S. House of Representatives in 1884, 1886, 1888, and 1892. He was a delegate to the Republican National Convention in 1884, 1888, 1892, 1904, 1908, and 1916. In 1897, he was a member of the executive committee at the national monetary conference in Indianapolis, Indiana, where he advocated a sound money position.
In 1903, Willson sought the Republican gubernatorial nomination. He had the backing of William O. Bradley, who in 1895 had become the first Republican governor in the state's history. Others at the convention favored Louisville businessman Morris B. Belknap. After a ruling against a contested delegation to the convention, Willson withdrew his candidacy. Bradley, angered that the party had not united behind his candidate, boycotted the convention. Belknap was handily defeated by Democrat J. C. W. Beckham in the general election.
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