Francis Winston, originally a Republican, became a leading Democrat after objecting to the inclusion of African Americans in the political alliance between his party and the Populists.
He helped lead the Democrats' white supremacy campaigns in 1898 —when he was elected to the North Carolina House of Representatives— and in 1900.
When The University of North Carolina at Chapel Hill reopened in 1875, he transferred there as the first student to register.
The following year he taught school and studied law with his father, Patrick Henry Winston.
Charles B. Aycock, a college friend of Winston, appointed him Judge of superior court for the second Judicial District.