Sengbe Pieh, the hero in this episode, was born about 1813 in the town of Mani in Upper Mende country, a distance of ten days' march from the Vai or Gallinas coast. Said to have been the son of a local chief, he was married with a son and two daughters. Sengbe, a farmer, was going to his field one day in late January 1839, when he was captured in a surprise attack by four men, his right hand tied to his neck. He was taken to a nearby village where he passed three days with a man called Mayagilalo, apparently the boss of his captors. Indebted to the son of the Vai King Manna Siaka, Mayagilalo gave over Sengbe to him in settlement. After staying in Siaka's town for a month, Sengbe was marched to Lomboko, a notorious slave-trading island near Sulima on the Gallinas coast, and sold to the richest slaver there, the Spaniard Pedro Blanco, whose activities had helped to make King Siaka wealthy as well.

At Lomboko, Sengbe was imprisoned with other slaves, while fresh ones joined them for the two months they were there, waiting to be transported across the Atlantic. Most of the captives came from Mende country, but others were Kono, Sherbro, Temne, Kissi, Gbandi (in present-day Liberia), and Loma (in present-day Liberia and in Guinea, where they are known as Guerze). Some, who did not speak Mende, learned the language during their forced journey through Mende country to the coast. Most were farmers, but it is said that others were hunters and blacksmiths. This is surprising, because all over West Africa blacksmiths held a sacred place in society and could neither be enslaved nor killed even in war.

All these people were shipped from Lomboko in March aboard the schooner Tecora, which arrived at Havana in the Spanish colony of Cuba in June. At a slave auction following advertisement, Jose Ruiz, a Spanish plantation owner, bought Sengbe and forty-eight others for $450 each to work on his sugar plantation at Puerto Principe, another Cuban port three hundred miles from Havana. Pedro Montez, another Spaniard bound for the same port, bought four children, three girls and a boy. On June 26, the fifty-three Africans were herded on board an American-built schooner, originally called Friendship, but changed to the Spanish La Amistad when the vessel changed ownership and registration to a Spanish subject. Although Spain had prohibited the importation of new slaves into her territories since 1820, the two Spanish planters were able to obtain official permits to transport their slaves. They chartered the Amistad from Ramon Ferrer, who was both owner and captain. Apart from the fifty-three Africans and their Spanish owners, the schooner carried a crew comprising the master, Ferrer; his two black slaves, Antonio (the cabin boy) and Celestino (the cook); and two white seamen. The ship also carried a cargo of dishes, cloth, jewelry, and various luxury items and staples. The cargo was insured for $40,000. Ruiz insured his forty-nine slaves for $20,000, while Montez insured the four children for $1,300.