He had been a strong supporter of Martin Witherspoon Gary in his gubernatorial campaign of 1880 which got him noticed by those opposed to the Conservative wing of the state Democratic party.

[1] In 1882, Sheppard was placed on the Democratic statewide ticket for the post of Lieutenant Governor and easily won election and reelection in 1884.

When Hugh Smith Thompson resigned on July 10, 1886, to be Assistant Secretary of the Treasury, Sheppard succeeded to the governorship.

In the nomination battle to be the Democratic nominee for governor in the election of 1886, he was promoted by Benjamin Tillman and the News and Courier.

In 1908, Sheppard was the president of the South Carolina Bar Association and was member of the state Senate for a second time from 1919 to 1920.