Westcott was born in
Alexandria, DC where his father, James Sr., was transitioning from newspaper publisher to politician. James Jr.'s grandfather was a captain in the
American Revolutionary War. When Westcott was young, his family moved to
New Jersey where his father established a political career in the
Assembly and as
Secretary of State of New Jersey from 1830 to 1840. James Jr. married Rebecca Bacon Sibley on August 7, 1821. He studied law and was admitted to the
bar while still in his early 20s. In 1830, he moved to the
Florida Territory and was appointed territory secretary by
Andrew Jackson. His duties sometimes included performing the duties of the governor when the governor was away — all while barely 30 years old. ==Duel==