[2] In 1823, Westcott's father, through his association with the Delaware and Raritan Canal Company, became friends with Samuel L. Southard, one of New Jersey's United States senators.

Westcott instead began studying medicine at the University of Pennsylvania in Philadelphia, primarily focusing on the treatment of yellow fever and dysentery.

Yellow fever was prevalent in Florida's swamps, and there weren't many trained doctors who knew how to treat the disease in the territory.

Westcott enlisted in the U.S. Army in 1840, serving as a surgeon in the Florida Mounted Volunteers under the command of Colonel William Bailey.

Westcott saved his regiment from disaster multiple times, most notably preventing them from marching into a Seminole ambush in the San Pedro Swamp.

Westcott also began working closely with the army after coming to the conclusion that the swamps, though inhospitable for human settlement, were the perfect hiding spots for Seminole war camps.

With the help of the army, Westcott began destroying Seminole food sources and forward camps, forcing the tribe into a limited area of operation around the Everglades.

In 1854, James E. Broome, the governor of Florida, shared Westcott's belief that a peaceful resolution was possible, and enlisted the aid of the Oklahoma Seminoles to try to persuade their kinsman to surrender.

[3] As a result of pressure from many politicians, the U.S. Secretary of War, Jefferson Davis, outranking Westcott and Broome, commanded the army to begin aggressive reconnaissance of the Everglades in an attempt to provoke a Seminole response.