Little is known about Samuel Willoughby, the immigrant businessman for whom Willoughby Avenue and Willoughby Playground are named. He moved to the United States when he was 19 and entered the dry goods business. In 1830, he married Margaretta Duffield, the daughter of one of Brooklyn’s wealthiest families. According to business directories at the time, he founded the Brooklyn Bank in 1832 and sat on the board of directors of the Brooklyn Fire Insurance Company and the Long Island Insurance Company. Willoughby also developed business property in downtown Brooklyn on a triangle bounded by what are now Pearl, Fulton and Willoughby Streets.
Willoughby Avenue opened between Franklin and Nostrand Avenues in 1851, in 1867 it was expanded between Yates Street (now Marcus Garvey Boulevard) and Broadway, and the final section between Tompkins and Throop Avenues was added in 1871.