Thorowgood Smith (1744-1810) was a merchant-shipper that established himself in Baltimore during the 18th century. He owned 26 acres of land in what is now known as the Union Square neighborhood. In 1799 Smith’s stately manor, Willow Brook, was completed making it one of the finest abodes in the city. Financial hardships occurred when Smith’s shipping investments went south and he was forced to sell the mansion. Around 1802 Smith moved into a small home on the edge of town that still stands today. Situated in Shot Tower park, the House at 9 North Front Street is maintained by the Women’s Civic League. Smith was the city’s second mayor, holding the post from 1804 to 1808. When he died in 1810, his estate was left to his wife and then nephew, John Donnell. Donnell began dividing the property into lots for sale as the harbor and adjoining communities began to thrive.
Smith wore personally designed eyeglasses attached by a ribbon that wrapped around the top of his head. This distinctive look was used by Smith to avoid pinching the bridge of his nose. The portrait is located in room 215 of City Hall. It once hung in the Peale Museum.