Congressman Robert Smalls, who stole a steamboat in the harbor and sailed it out past the Confederate held Fort Sumter and turned it over to the blockading Union Fleet, served as a waiter in the hotel's dining room before the war.

However, in 1935, at the height of the Great Depression, after Milton Pearlstine made the property available to the City of Charleston and at the urging of Mayor Burnet Maybank and other notable citizens, the original building became a Works Progress Administration project.

Modeled on 18th century London playhouses by Charleston architect and pioneering preservationist Albert Simons, the present Dock Street Theatre's stage house and auditorium were built in the hotel's courtyard.

This extensive full-scale renovation brought the historic theatre into the 21st century with state-of-the-art lighting and sound, modern heating and air conditioning, and new restrooms and seating.

[citation needed] In addition more than 15,000 South Carolina students enjoy special school day performances offered by Charleston Stage each year at the Historic Dock Street Theatre.