Born in 1852 at Windsor, Bertie County, North Carolina, Winston was educated in the Horner School, located in Oxford, North Carolina; the University of North Carolina, which he entered at the age of thirteen; the United States Naval Academy, where he ranked first in his class; and Cornell University, where he was awarded the Latin Scholarship Medal and elected a member of the Phi Beta Kappa Society.
On the reorganization of the University of North Carolina in Chapel Hill in 1875, he was elected assistant professor of literature, and the following year he was promoted to full professor of Latin. He eventually became president of that university, and later he served as the first president of the University of Texas.
In 1899 Winston became the second president of the North Carolina College of Agriculture and Mechanic Arts. While in office, the college developed a new curriculum in textiles, and it first offered summer courses for public school teachers. Winston retired in 1908 and accepted a lifetime annuity from the Carnegie Foundation for his service to southern education. He died in Durham, North Carolina, in 1932.

