[2] His mother Nancy was the daughter of Caesar Nero Paul, a man of African descent who was enslaved at the age of fourteen as a house-boy in the Maj. John Gilman House, and later became free in 1771 after capture in the French and Indian Wars.
The house on the idyllic tree-lined lane is described in the historical memoirs of Elizabeth Dow Leonard: "Near the bridge, lived our friend Whitfield in a pretty cottage surrounded by hollyhocks, bachelor's buttons, poppies, saffron, and caraway, and the leafy orchards of their more wealthy neighbors.
The poem embodies many of Whitfield's ideas about the hypocrisy of American freedom and democracy, and the difficult lives for both freed and enslaved Africans in the US.
[11] Another of his famous poems, written in 1867 after the Civil War, deals with the topic of the two ships that sailed to the New World in 1620, marking the dual beginnings of America and slavery.
The poem's introduction:[12] More than two centuries have passed Since, holding on their stormy way, Before the furious wintry blast, Upon a dark December day, Two sails, with different intent, Approached the Western Continent.
One vessel bore as rich a freight As ever yet has crossed the wave; The living germs to form a State That knows no master, owns no slave.
The trafficker in human souls Had gathered up and chained his prey, And stood prepared to call the rolls, When, anchored in Virginia's Bay— Frederick Douglass visited Whitfield's barber shop in 1850.
From their discussion, Douglass became deeply impressed by Whitfield's poetic abilities, calling him in the Anti-Slavery Bugle a "sable son of genius."
[8] Beyond abolitionism, Whitfield originally became a prominent member of the Colonization Movement, which promoted African American emigration to Africa and indigenous parts of South or Central America.
Whitfield became involved in a proposal by Missouri Senator Frank P. Blair to establish a colony for black colonization in Central America.