Paddock was a financier and entrepreneur and was involved in numerous ventures. One of his most notable achievements was his founding of the Black River Bank in 1844, of which he served as president.
Paddock's legacy, though, lies in the Paddock Arcade. During the rebuilding of Watertown after the Great Fire of 1849, Paddock commissioned architect Otis Wheelock to design and build the arcade and the adjoining Paddock Building. Paddock had taken notice a photo of the Beauharnais Arcade in Paris, France. This famous "glass covered street" struck Paddock, who wanted to build one in Watertown. Opened in 1850, the arcade today carries the distinction of being the oldest, continuously operating covered mall in the United States.