Mastering Paradox: John Jay as a Slaveholding Abolitionist

By David N. Gellman

“Alexander Hamilton, Enslaver? New Research Says Yes” announced the New York Times in a November 2020 news story. A paper published online by Jessie Serfilippi, a researcher at the Schuyler Mansion State Historic Site, uncovered striking new evidence to clarify long muddied waters about Hamilton’s personal connections to this deep-seated New York institution. Serfilippi’s dogged research is proof once again that even traditional archives still hold revelations.[1] The story sits at the intersection of Broadway, Black Lives Matter, the 1619 Project, and the enduring hold the founding fathers have in American culture. In Lin-Manuel Miranda’s musical, the honor-obsessed, forward-thinking founding father’s hip-hop persona is, among other things, a foil for Thomas Jefferson, whose smooth style cannot mask his identity as a hypocritical southern slaveholder. The Virginia plantation owner’s African American mistress is no secret to 21st century audiences watching the action unfold.[2] Now, it would seem, Hamilton’s own slavery secret is out in the open too.

For biographers of Alexander Hamilton, revisions are clearly in order. Ron Chernow’s bestselling biography placed the founder on the side of the angels by emphasizing Hamilton’s participation in the New-York Manumission Society (NYMS) and projecting an abiding dislike of slavery into Hamilton’s character. Clear evidence of Hamilton’s ownership of other human beings, his procurement of enslaved servants for relatives, and his assistance to slaveholding clients must not be waved off as minor discordant notes in understanding this consequential figure.[3] Serfilippi’s findings will stimulate scholars to reconstruct stories of the enslaved people in Hamilton’s household — lives not reducible to long-lost scribbles in Hamilton’s ledger. Moreover, as Serfilippi puts the matter, “it is vital that the myth of Hamilton as the ‘Abolitionist Founding Father’ end.”[4]

John Jay in his judicial robes as the first Chief Justice of the U.S. Supreme Court. https://history.nycourts.gov/u-s-chief-justice-john-jay-when-all-judges-were-originalists/

My research on John Jay, another slaveholding New York founding father with a prominent connection to abolitionism, affirms that need to replace myth with a more confounding reality. Hamilton married into New York’s enslaving elite. John Jay was born into that elite, and by marrying Sarah Livingston, further cemented his class ties. Even so, in 1785, Jay became the inaugural president of the NYMS. Jay resigned from the NYMS in 1789 when he became the inaugural Chief Justice of the US Supreme Court. He may have done so out of concern that his membership might pose a conflict of interest if a case involving slavery came before him. If so, it is unlikely that it occurred to Jay to divest himself of his human property — the 1790 census records his ownership of five people — based on this logic.[5]

Jay was hardly alone as a slaveholder who participated in New York City’s pioneering Manumission Society. Three decades ago, historian Shane White found twenty-seven slaveholders in the 1790 US Census among the society’s members, with eight men in the group’s ranks acquiring slaves by the time of the 1800 census.[6] We can now add Hamilton to that latter group. Ironically, during the early years of the NYMS, Hamilton participated in a committee that unsuccessfully attempted to impose a rule requiring members to divest themselves gradually of their enslaved human property. Would Hamilton have curbed his desire for enslaved servants had his earlier initiative been successful? Would it have made a difference to the Society’s first president John Jay?[7]

The intersection of the personal and political is everywhere one cares to look with John Jay. From 1785 to his retirement from public service in 1801, Jay critiqued the institution of slavery in some spheres, but acquiesced with regard to the protection of slavery in the US Constitution. At almost every turn, whether in the United States or abroad, he had enslaved servants by his side. The personal responsibility he felt toward some enslaved and formerly enslaved servants at other times lapsed into callous incomprehension. The African American men and women he held in slavery facilitated his public labors. Their actions, objections, and suffering illustrated indignities that Jay both criticized and perpetrated.

John Jay became President of the NYMS in early 1785 as he entered his political prime. At age thirty-nine, he was the confederation’s chief foreign policy officer, after having helped negotiate the treaty that secured American independence. Jay believed in the mission of this organization. The preamble to the New York society’s rules, adopted at a meeting Jay chaired, stated the goal “to enable” slaves “to Share, equally with us, in that civil and religious Liberty with which an indulgent Providence has blessed these States. . . .”[8] In 1786 Jay reflected that slavery required people to work “at the pleasure of Persons, who were not created more free, more rational, more immortal, nor with more extensive Rights and Privileges than they were!”[9] Jay predicated his engagement in organized antislavery on the notion of fundamental equality.[10] Jay also helped do the work. Stymied in their effort to pass a gradual emancipation bill on the model of Pennsylvania, Connecticut, and Rhode Island, Jay and his colleagues encouraged the New York state legislature to make it easier to free the enslaved and close state borders to commerce in slaves. Such laws curtailed the previously almost absolute prerogative to acquire and sell human property.[11]

Simultaneously, as Secretary of Foreign Affairs during the Confederation period, Jay confronted the excessive demands of slaveholders. The 1783 Peace of Paris, which Jay played an integral role in negotiating, prohibited the British from “carrying away any Negroes or other property.”[12] In his 1786 report to the Continental Congress, Jay dismantled the notion that the British evacuation of thousands of formerly enslaved people should stand in the way of fully implementing the treaty. Jay posed to Congress the imaginary scenario of France promising freedom to Americans held in captivity by Algiers and then returning those Americans to slavery after the conclusion of a peace treaty with the Mediterranean power: “Is there any other difference between” British actions and hypothetical French actions, “than this . . . that the American slaves at Algiers are white people, whereas the African slaves at New York were black people?”[13] Jay also labelled as “cruelly perfidious” any notion that the British would return actual people who relied on their promises of liberation. The just solution was for the British to offer up “full value” in monetary compensation. But to Jay compensation acknowledged that slavery was wrong rather than right.[14]

His strong support for ratification of the US Constitution makes clear that Jay had little will to fight domestic slavery on the national level. British abolitionist Granville Sharp confronted Jay with the new charter’s severe shortcomings with regard to slavery. Jay offered a simple explanation: “local interests” had to “be gratified” to secure union. Still, Jay offered up New York as an encouraging example. The state legislature had liberalized private manumission laws; white New Yorkers could no longer legally import or export slaves from the state; and slaves confiscated from loyalists during the Revolutionary War now could claim their freedom.[15]

“Local interests” in New York, however, regarded even the prospect of gradual emancipation as dangerous. Running for governor in 1792, Jay learned that some voters found his erstwhile association with the NYMS to be a negative. Still, Jay reiterated the Society’s goal “to protect a poor & friendless race” under the principle that “every man of every color and description has a natural right to freedom.” He lost the election by a razor-thin margin.[16]

Two years later, Jay’s diplomatic mission to forestall war with Britain bolstered his antislavery inclinations. Jay did not regret his inability to persuade the British to accommodate American demands for compensation for formerly enslaved people who evacuated the United States at the end of the Revolutionary War in alleged violation of Article VII of the 1783 peace treaty. In reporting to Secretary of State Edmund Randolph his debate with negotiating partner Lord Grenville, Jay dropped a small bombshell. “I confess,” he wrote, his British counterpart’s “Construction of that Article has made an impression upon my Mind, & induced me to suspect that my former opinion on that Head was not well founded.” In other words, Jay agreed with Lord Grenville, that American claims for compensation were, in effect, an “Odious” attempt to apply the logic of slavery to free people. Alexander Hamilton, in his public defense of the treaty, took up the same logic and same language to beat back criticism.[17]

And yet, emblematic of Jay’s exercise of personal slaveholding privilege, an enslaved man named Peet was part of his small London entourage. This same man, who Jay purchased in 1790, had accompanied him domestically when the Chief Justice rode circuit.[18] Peet had a wife back home in New York. Writing to his wife Sarah from London in August 1794, Jay noted, “Peet begins to wish himself Home again. The novelty is a good deal over.”[19] The jurist-diplomat liked to think of himself as kind and considerate toward those who were loyal to him. The next month, he wrote from London urging his nephew Peter Jay Munro to care for the formerly enslaved Old Mary: “if she should suffer I should be hurt and mortified.” The diplomat insisted, “The Claims of Humanity . . . must always be primary object of attention”; thus, Munro should charge Jay for “whatever necessities may require.”[20]

Meanwhile, things did not get better for Peet in England. The other servants John Jay employed locally during the London stay hazed and tormented the enslaved African American. Yet, while Jay took his time socializing in England, including with the great Parliamentary abolitionist William Wilberforce, Peet had to endure until their Spring 1795 return. The whole set up underscored John Jay’s power and leverage. The married Peet was unlikely to avail himself of the Somerset principle laid down by Lord Mansfield in 1772 — that an American slave could not be compelled to return to American slavery from free English soil.[21]

When John Jay and Peet returned from England, the governorship of New York State awaited. One of the most remarkable events of Jay’s second term would be the passage of a gradual emancipation law that freed children born after July 4, 1799 to enslaved mothers, but required those same children to serve their mothers’ masters until age of 25 if female and 28 if male. John Jay appears to have stayed out of the way as the bill worked its way through the legislature, though there is no doubt of his approval. During this period, he maintained a staff of enslaved servants whose needs were distinctly subordinate to his. In 1797, the governor purchased a woman named Dinah, who he intended to free “after serving me faithfully a certain Term.” He did not, however, want her two-year-old child in the household and tried to find a New York City relative to take the child off his hands. Instead, he subsequently sold them both for a term of years to someone else, with, as it turned out years later, dangerous consequences for the child.[22]

Governor Jay’s awareness of appearances jostled with his desire for authority within his own household. In 1797, Jay had his enslaved servant Caesar transferred from Manhattan to his Albany household. Jay found Caesar so difficult that he feared the neighbors might take note. Caesar was apparently too old for corporeal punishment to do any good “and my Situation forbids any Experiments of that kind.” He solved his problem by passing Caesar on to his son, an aspiring New York City attorney who joined the NYMS in 1798. Peter, his father instructed, “must have a Servant,” by which the governor meant a slave. If Peter found Caesar to be too much trouble then “sell him, and with the money buy another.” Even though the governor wished to see the institution of slavery wind down, the Governor was training Peter to be a master, telling his son, “I set no Price because you are to treat him and do . . . with him as your own.” Sometime in 1798, Caesar ran away to become a sailor.[23]

The articulation of antislavery principles, the support for a gradual process of emancipation, and the endurance of self-serving mastery all defined John Jay’s post-Revolutionary War public life. The principle that slavery must end made its mark on the institutional histories of slavery and politics in New York for decades to come. John Jay’s personal interests registered directly on the lives of the people John Jay purchased and exchanged. The rebuke their needs and their resistance represented he only dimly acknowledged.

Jay spent his retirement at his home in Katonah, New York in Westchester County. http://johnjayhomestead.org/explore/

The interweaving of personal and political persisted during his almost three decades of retirement (1801-1829) on his Westchester County farm. His elder son, Peter Augustus Jay, and his nephew, Peter Jay Munro, each ascended to the presidency of the NYMS. His younger son, William, took his first tentative steps toward the abolitionist cause in the 1820s; within six years of his father’s death William Jay embraced immediate abolitionism with an abiding passion.

Graveston of Zilpah Montgomery. Photo Courtesy of John Stockbridge, Bedford Town Historian.

For decades to come, Zilpah Montgomery, a woman born into slavery in John Jay’s household who spent much of her life in service to Jay and his descendants, embodied the complicated enslavement and emancipation pattern. In 1809, the retired John Jay banished the enslaved Zilpah from his household for getting pregnant. At the urging of Zilpah’s enslaved mother Clarinda, John Jay brought her back to the household in 1811 after the child died.[24] He freed Zilpah at age 25, in accordance with the gradual emancipation formula established by the 1799 law, even though her pre-1799 birth meant that the law itself did not legally apply to her.[25] She remained associated with the household until her death in 1872. She is buried in the Jay family’s Bedford, New York churchyard plot. During the Reconstruction era, the entangled growth of enslavement and abolition, of private and public, finally reached an end.

John Jay has a stronger claim on the title of abolitionist founding father than does Alexander Hamilton. The disturbing but consequential nature of that abolitionism, like the recent revelations about Hamilton, should prompt a further recognition that the only way to properly appraise slavery and the founders is to place the subject in the foreground. William Jay, who revered his father and named his own son John Jay II, began one of his major antislavery books by writing: “Our Fathers . . . entered into a guilty compromise on the subject of Slavery, and heavily is their sin now visited upon their children.”[26] Twenty-first century Americans contemplating the historical legacies of slavery may not reach all the same conclusions nor use the exact same language as a founder’s 19th-century son. But he undertook this work. So must we.

David N. Gellman is Andrew Wallace Crandall Professor of History and Chair of the Department of History at DePauw University. He is author of the forthcoming book Liberty’s Chain: The Jay Family, Slavery, and Emancipation, 1685-1912, to be published in 2022 by Three Hills, an imprint of Cornell University Press.

[1] Jessie Serfilippi, “‘As Odious and Immoral a Thing’: Alexander Hamilton’s Hidden History as an Enslaver,” Schuyler Mansion State Historic Site, https://parks.ny.gov/documents/historic-sites/SchuylerMansionAlexanderHamiltonsHiddenHistoryasanEnslaver.pdf; Jennifer Schuessler, “Alexander Hamilton Enslaver? New Research Says Yes,” New York Times, November 11, 2020 (updated), https://www.nytimes.com/2020/11/09/arts/alexander-hamilton-enslaver-research.html; see also, David Kindy, “New Research Suggests Alexander Hamilton Was a Slave Owner” Smithsonianmag.com, November 10, 2020, https://www.smithsonianmag.com/history/new-research-alexander-hamilton-slave-owner-180976260/.

[2] See contributions to “Symposium on Hamilton” for ways in which scholars are unpacking racial and other historical meanings in Lin-Manuel Miranda’s cultural landmark of a musical, especially Heather S. Nathans, “Crooked Histories: Re-presenting Race, Slavery, and Alexander Hamilton Onstage,” 271, and Marvin McAllister, “Toward a More Perfect Hamilton,” 286-7; Ankeet Ball, “Ambition & Bondage: An Inquiry on Alexander Hamilton,” Columbia University & Slavery website https://columbiaandslavery.columbia.edu/content/ambition-bondage-inquiry-alexander-hamilton-and-slavery, offers a thoughtful appraisal of Hamilton. Ron Chernow, Alexander Hamilton (New York: Penguin, 2004); Michael D. Chan, “Alexander Hamilton on Slavery.” The Review of Politics 66 (2004): 207-231, provide positive interpretations of Hamilton’s antislavery commitments; Rob N. Weston “Alexander Hamilton and the Abolition of Slavery in New York,” Afrio-Americans in New York Life and History 18 (1994): 31-45, is more critical; for a sampling of scholarship on Jefferson and slavery, see Annette Gordon-Reed, The Hemingses of Monticello: An American Family (New York, W.W. Norton, 2008); Henry Wiencek, Master of the Mountain: Thomas Jefferson and His Slaves (New York: Farrar, Straus and Giroux, 2012); David K. Shipler, “Jefferson Is America—And America Is Jefferson.” New York Times, April 12, 1993.

[3] Chernow, Alexander Hamilton, 6, 23, 33, 41, 121-2, 210-16, 239, 495, 580-1, 629, 730; for Chernow’s response to the new evidence, see the New York Times and Smithsonian articles cited above.

[4] Serfilippi, “As Odious,” quotation 28, and throughout.

[5] John Jay to John C. Dongan, Feb. 27, 1792, The Selected Papers of John Jay, ed. Elizabeth M. Nuxoll (Charlottesville: University of Virginia Press, 2017), 5:361-2; William Jay, The Life of John Jay (New York: J. & J. Harper, 1833), 1:235; Daniel Littlefield, “John Jay, the Revolutionary Generation, and Slavery.” New York History 81 (2000): 91-132, offers a valuable assessment; Jan Horton, “Listening for Clarinda,” unpublished ms. report for John Jay Homestead Historic Site (2000), is a powerful unpublished study. The author of the most recent full biography of John Jay, Walter Stahr, John Jay (New York: Hambledon and London, 2005), 236-9, 346-7, moves through the issue of slavery during this era rather quickly.

[6] Shane White, Somewhat More Independent: The End of Slavery in New York City, 1770-1810 (Athens: University of Georgia Press, 1991), 81-6.

[7] New York Manumission Society Records, 1785-1849, Manuscript Collection Relating to Slavery, New-York Historical Society, https://cdm16694.contentdm.oclc.org/digital/collection/p15052coll5/id/31512 (hereafter NYMS), 6:16, 29-30, 37-8, 40, 61; Chernow, Hamilton, 215.

[8] NYMS, 6:3-4.

[9] John Jay to John Murray, Jr. (draft), Oct. 10, 1786, The Papers of John Jay - Online Edition (hereafter PJJ), Columbia University Libraries, https://dlc.library.columbia.edu/jay, Doc. 07283; Jay crossed out these words in the note he drafted to accompany the contribution he was to pass along to the NYMS treasurer.

[10] Paul J. Polgar, Standard Bearers of Equality: America's First Abolitionists (Chapel Hill: UNC Press, 2019), 53-4, 103-10, 289, and throughout, makes a strong argument for the scope and sincerity of the NYMS’s antislavery commitments and the first wave of northern abolitionists more broadly; see also Manish Sinha, The Slave’s Cause: A History of Abolition (New Haven: Yale University Press, 2016), for a synthesis that gives this early period careful attention; Littlefield, “John Jay,”121, also notes Jay’s lack of racist presumptions.

[11] Evidence of Jay’s participation can be found regularly in the first 130 odd pages of NYMS, Vol. 6, For more on the NYMS and its early program and achievements, see David N. Gellman, Emancipating New York: The Politics of Slavery and Freedom, 1777-1827 (Baton Rouge: LSU Press, 2006), 56-77; and James Oakes, Freedom National: The Destruction of Slavery in the United States, 1861-1865 (New York: W.W. Norton, 2013), 10-12.

[12] “The Definitive Treat of Peace 1783,” The Avalon Project, Yale Law School, http://avalon.law.yale.edu/18th_century/paris.asp; for my extensive analysis on the treaty’s handling of slavery set in the context of Jay’s wartime slaveholding activities, see David Gellman, “Abbe’s Ghost: Negotiating Slavery in Paris, 1783-4,” in Experiencing Empire: Power, People, and Revolution in Early America, ed. Patrick Griffin (Charlottesville: University of Virginia Press, 2017), 189-211.

[13] John Jay, Secretary of Foreign Affairs, October 13, 1786, Secret Journals of the Acts and Proceedings of Congress, From the First Meeting Thereof to the Dissolution of the Confederation, By the Adoption of the Constitution of the United States (Boston: Thomas B. Wait, 1821), 4:277 [italics in original].

[14] Jay, Secret Journals, 4:278; for a lucid analysis of Jay’s comments in this report, see James Oakes, The Scorpion’s Sting: Antislavery and the Coming of the Civil War (New York: W.W. Norton, 2014), 113-5. See also, John P. Kaminski, “John Jay’s Diplomacy During the Confederation,” New York History 83 (2002): 283, 295, 322-3; Kaminski emphasizes the attitude of “moral statesmanship” (295) that guided Jay while he held this crucial post.

[15] John Jay to English Anti-Slavery Society, n.d., 1788, The Correspondence and Public Papers of John Jay, ed. Henry P. Johnston (New York: G.P. Putnam’s Sons, 1890-3), 3:340-4.

[16] John Jay to Dongan, Feb. 27, 1792, in Selected Papers, 5:361-2; Gellman, Emancipating New York, 131-5; Littlefield, “John Jay,” 96-7, 107; Stahr, John Jay, 284.

[17] John Jay to Edmund Randolph, Sept. 13, 1794 [underlining in original], PJJ, Doc. 04312; Oakes, Scorpion’s Sting, 115-8; The Papers of Alexander Hamilton (New York: Columbia University Press, 196-1987), ed. Harold C. Syrett, 18:517-521, 19:100-105, written under the pseudonyms Camillus and Philo Camillus.

[18] Peter Jay Munro to John Jay, May 5 and May 11, 1790, PJJ, Docs. 00409, 00410; John Jay to Peter Augustus Jay, June 17, 1791, Selected Letters of John Jay and Sarah Livingston Jay, ed. Landa M. Freeman, Louise V. North, and Janet M. Wedge (Jefferson, N.C.: McFarland, 2005), 198; Selected Papers, 5:214-30, provides a highly informative account of Jay’s circuit-riding experience.

[19] Sarah Livingston Jay to John Jay, Apr. 22, 1794, John Jay to Sarah Livingston Jay, Aug. 16, 1794, Selected Letters, 224, 230.

[20] John Jay to Peter Jay Munro, Sept. 14, 1794, PJJ, Doc. 00427.

[21] Peter Augustus Jay to Nancy Jay, Nov. 8, 1794, John Jay to Sarah Livingston Jay, Mar. 13, 1795, Selected Letters, 239-40, 252-3; William Wilberforce to John Jay, Jan. 28, Feb. 7, May 11, Aug. 27, 1795; Nov. 7, 1805; see also, Feb. 4, 1798, PJJ, Docs. 90434, 09273, 09275, 09274, 09283, 04899; on the Somerset decision, see Seymour Drescher, Abolition: A History of Slavery and Antislavery (New York: Cambridge University Press, 2009), 99-105.

[22] John Jay to Richard Lawrence, Feb. 9, 1797, PJJ, Doc. 08969; Peter Augustus Jay to John Jay, Jan 21, 1808, PJJ, Doc. 06126; on the 1799 gradual emancipation law and the politics that produced it, see Gellman, Emancipating New York, chapter 6; William Jay, Life, 1:390-1; and Stahr, John Jay, 347.

[23] John Jay to Peter Augustus Jay, Oct. 2, 1797, Jay Family Papers, Huntington Library, San Marino, California; Peter Augustus Jay to Maria Jay Banyer, Oct. 8, 1797, typescript excerpted from Columbia University Libraries Manuscript Collections, held at John Jay Homestead Historic Site, Katonah, New York; NYMS, 9:10; for further wrinkles to Caesar’s story, see Peter Augustus Jay to John Jay, Feb. 22, 1800; JJ to PAJ, Mar. 3, 1800, PJJ, Docs. 11459, 13348; see also, Horton, “Listening,” 87-8, on Caesar’s discipline problems, and 73-4, 76-7, 81-4, 87-91, 101-6, 109-10, on John Jay’s slave management and disciplinary style.

[24] The details of this story and surrounding events can be followed through the following correspondence: Peter Augustus Jay to Maria Jay Banyer, Oct. 21,1809; Sarah Louisa Jay to JJ, Jan. 15, 1810, John Jay to Peter Augustus Jay, Apr. 16, May 8, 1811, Mar. 9, 1813, Peter Augustus Jay to John Jay, Mar. 12, 1813, PJJ, Docs. 10046, 09245, 11518, 11519, 11555, 06180

Horton, “Listening,” 101-4.

[25] JJ to PAJ, Mar. 12, 1817, PJJ, Doc. 90065; Horton, “Listening,” 109-10.

[26] William Jay, A View of the Action of the Federal Government, in Behalf of Slavery (New York: J.S. Taylor, 1839), 13.