Since he was always interested in railroads, Flint served as the superintendent of the CCC&I from 1859 to 1878. Flint became a member of the Cleveland board of schools in 1860 and was elected mayor in 1861. Flint, a Republican because of the Civil War, later realigned his views to that of a War Democrat;  he supported the North's cause during the Civil War.
As someone who had always been drawn to railroads, Flint held the position of superintendent at CCC&I from 1859 to 1878. He joined the Cleveland school board in 1860 and was elected mayor in 1861. Flint initially identified as a Republican because of his opposition to the Civil War, but later aligned himself with the views of a War Democrat; he actively supported the North's cause during the conflict.