At the outbreak of the American Civil War he enlisted in the 5th Virginia Cavalry and was eventually promoted to an aide under General Thomas L. Rosser. After the war ended, Winston pursued a farming career for a number of years before moving to Minneapolis in 1872. In 1888 he was nominated by the Democratic party to run for mayor of Minneapolis but lost the election to Edward C. Babb.
In 1890 he ran again and was successful, serving one term from 1891 to 1893.
He also served two terms in the Minnesota House of Representatives from 1893 to 1895 and from 1899 to 1901. Winston died in Chicago, Illinois on July 1, 1901.
He is buried in his family"s private cemetery in Hanover County, Virginia. Minneapolis Mayoral Election, 1888
Edward Charles Babb 17,882
Philip Bickerton Winston 14,759
William J. Dean 1,365
Baldwin Brown 2
Hugh Galbraith Harrison 1
Write-Insurance and Scattering 1
Minneapolis Mayoral Election, 1890
Philip Bickerton Winston 17,200
Edwin G. Potter 11,000
Edwin Phillips 1,251
Ernest F. Clark 973.