John Jay, the first Chief Justice of the United States, was a staunch opponent of slavery. Unsuccessful in prohibiting slavery in New York’s first state constitution in 1777 and in the early state legislatures, Jay became the first president of the New York Manumission Society in 1786—a position he resigned from only when he became Chief Justice in 1789.

In March 1785 Jay wrote that he “wish[ed] to see all unjust and unnecessary Discrimination every where abolished; and that the Time may soon come when all our Inhabitants of every Color and Denomination shall be free, and equal partakers of our political Liberty” (to Benjamin Rush, New York, 24 March 1785). Six months later, Jay wrote “that Men should pray and fight for their own Freedom, & yet keep others in Slavery, is certainly acting a very inconsistent as well as unjust & perhaps, impious part—but the History of Mankind is filled with Instances of human Improprieties” (to Richard Price, New York, 27 September 1785). Another six months later, Jay again wrote that “To contend for our own liberty, and to deny that blessing to others, involves an inconsistency not to be excused” (to Richard Lushington, New York, 15 March 1786). Espousing these noble sentiments, John Jay, however, owned a slave. Was he hypocritical?
While serving as president of the Continental Congress in 1779, Jay was appointed as America’s first minister to Spain. On the voyage across the Atlantic in October 1779, the American frigate The Confederacy suffered severe damages during a storm losing its bowsprit, main mast, and mizzen mast. The captain deferred to Jay to decide whether to turn back, to proceed to Spain, or to put in to the French West Indies for repairs. Jay chose the latter, and the ship arrived at St. Pierre in Martinique on 18 December 1779. On the island for ten days before embarking on the Aurora, a French frigate, Jay and his wife Sarah witnessed the horrors of a slave auction. Among the captive Africans being sold was a fifteen-year-old boy named Benoit. Realizing that Benoit would likely die within two years if he worked on a sugar plantation on the French island, Jay purchased him. For the next four years, Benoit served Jay as a slave.
On 21 March 1784, Jay wrote a conditional manumission specifying that Benoit would be free in three years after he had served a sufficient time to moderately compensate Jay for his expense in the purchase. Jay wrote in the manumission document that “the Children of Men are by Nature equally free, and cannot without Injustice be either reduced to, or held in Slavery” (Jay Papers, III, 569). Shortly after Benoit was freed, Jay wrote in June 1788 to the English Anti-Slavery Society “that they who know the value of liberty, and are blessed with the enjoyment of it, ought not to subject others to slavery, is, like most other moral precepts, more generally admitted in theory than observed in practice.” Was John Jay a hypocrite?