(Lived December 8, 1854 – February 14, 1896)

Hugh Whiteside, son of James Whiteside, one of Chattanooga’s business leaders in the 1850s, graduated from the University of the South in 1879.  He entered St. Louis Law College, and upon graduation, returned to Chattanooga to practice.  Just two years after returning the Chattanooga, Whiteside became the first person born in Chattanooga to be elected mayor.  Mayor Whiteside also became the first mayor to serve a two-year term, as a change in the city charter in 1883 mandated that, beginning with the November 1883 election, all mayors serve a two-year term running November to November.   
 
Mayor Whiteside did not seek reelection, instead choosing to run for county judge in 1885.  Winning the election, Whiteside served as county judge until his death in 1896.