His land included the site of a black fraternal hall now known as the Sons of Beaufort Lodge, located at 607 West Street.

Gleaves, like his business partner Robert Smalls, went into politics and helped establish the Union League and the South Carolina Republican Party.

In 1876, Gleaves was a delegate to the 1876 Republican National Convention which chose Ohio Governor Rutherford B. Hayes as its nominee.

[3] Democratic Governor Wade Hampton appointed Gleaves to the position of trial justice in Beaufort but he declined and moved out of state.

However, following the 1880 presidential election, he returned to South Carolina when President James A. Garfield appointed him to the lucrative position of special customs inspector.