Cheshire Academy alumni

American financier, banker, and art collector (1837–1913)

American novelist (1927–2001)

James David Van Der Beek was an American actor. Known for his portrayal of Dawson Leery on The WB's Dawson's Creek (1998–2003), he also played a fictionalized version of himself on the cult ABC sitcom Don't Trust the B---- in Apartment 23 (2012–2013), starred as FBI agent Elijah Mundo on CSI: Cyber (2015–2016) and appeared as Matt Bromley during the first season of the FX drama Pose (2018).

American rapper from New York

American artist (1816-1872)

American government official; United States Secretary of the Navy from 1861 to 1869 (1802–1878)

Dominican Republic basketball player

American singer, songwriter and musician

British basketball player

Dominican-American basketball player (born 1977)

Cuban-American chief executive

American basketball player

American politician (1895–1968)

American theater critic, humorist and editor (1902-1958)