The Education of John Jay
America’s indispensable diplomat

Few could fathom why 55-year-old John Jay turned down President Adams’s nomination to rejoin the Supreme Court when his two terms as New York’s governor ended. What would lead him, in the hale prime of life, to retire instead to the plain yellow house he’d just built on a hilltop at the remote northern edge of Westchester County, two days’ ride from Manhattan, where visitors were few and the mail and newspapers came but once a week? After 27 years at the forge of the new nation’s founding, why would so lavishly talented a man give up his vital role on the world stage for the quiet life of a gentleman farmer?

But just that option—the chance for every man to sit quietly under his vine and his fig tree, with none to make him afraid—is what he had labored more than a quarter-century to bring about, and he felt he had achieved it. As the first chief justice both of New York and of the United States, as president of Congress and governor of his state, as secretary for foreign affairs and, most important, as the diplomat who stamped his vision on America’s foreign policy for generations to come, he had tried to ensure for his countrymen the peace, order, and stability that had seemed to him fragile and elusive from the moment he was born.

A sense of life’s fragility hung over Jay’s childhood; already at six and seven, his father described him as “very grave” and “very reserved,” though “indowed with a very good capacity.” He grew up with a keen sense that his Huguenot ancestors—refugees, like the Plymouth Pilgrims, from religious tyranny—had fled to the New World in the nick of time after France began persecuting Protestants in 1685. Before he was born, smallpox had blinded an elder brother and sister, for whom, he later wrote, “this world has not been a Paradize”; of his four other siblings, one was retarded and another emotionally disturbed. Shortly after John’s birth on Manhattan’s Pearl Street in 1745, his father moved his brood to a farm bordering Long Island Sound in Rye, an easier setting for his two blind children. Though Jay’s father had grown rich as a merchant, married a Van Cortlandt heiress, and counted most of the colony’s Dutch and Huguenot establishment as his relatives, and though he and his wife were loving parents, Jay’s childhood after he went to boarding school at age eight in the French-speaking Huguenot town of Nouvelle Rochelle had its share of privations. His eccentric schoolmaster treated his pupils “with little food and much scolding,” Jay’s son and biographer William reports. The boy struggled to keep the snow off his bed by blocking up his broken window with scraps of wood.

After entering six-year-old King’s College (later Columbia) at 14 (the normal age) and spending four happy years among his 20-odd fellow collegians, Jay—six feet tall, stick-thin, round-shouldered, fine-boned, with a sensitive mouth and thoughtful, melancholy eyes—began his law studies as a clerk for kindly Benjamin Kissam, who perceived at once the young man’s talent. Your “Whirl of Imagination,” he wrote his clerk, “bespeaks the Grandeur . . . of the Intellectual Source from whence the Current flows.” Fellow clerk Lindley Murray, whose school grammars and readers later sold in the millions, remembered Jay as “remarkable for strong reasoning powers, comprehensive views, indefatigable application, and uncommon firmness of mind.”

But Jay’s placid interval was short-lived. In the first year of his four-year apprenticeship, Parliament passed the Stamp Act. Six months later, the American Revolution had its prologue a few blocks from Kissam’s John Street office at New York’s old City Hall on Wall Street, where Federal Hall now stands. There the Stamp Act Congress convened in October 1765, only the second time that representatives of the American colonies had ever met together and the first time that they themselves, rather than royal authorities, had convened such a conclave—“a Measure which we Conceive of dangerous Tendency in itself,” the shocked Lords of Trade spluttered in London. More important, it was the first time that the colonies unitedly drafted a Declaration of Rights, in which they claimed “the Freedom of a People, and the Undoubted Right of Englishmen, that no Taxes be imposed on them, but with their own Consent.” Such big doings down the street—especially since one of New York’s five delegates to the Congress was a cousin of Jay’s and another was Judge Robert R. Livingston, father of Jay’s best friend—made so strong an impression on the 19-year-old that 11 years later, at the First Continental Congress, he effortlessly recalled in debate the rules that the Stamp Act Congress had followed.

Historians speak of the 1765 Congress, with its fulsome pledges of loyalty to the king, as conservative. It was a funny kind of conservatism, though; for when Judge Livingston, probable author of the group’s “Address to the King,” wrote New York’s London agent that no one should view the meeting as factious, since it aimed to divert Parliament from a course that sooner or later “will naturally render the colonies independent,” he was veiling a threat under an assurance. The New-York Gazette had already made that threat explicit four months earlier, writing that with Britain and her colonies at such cross-purposes, “the Connection between them ought to cease—and sooner or later it must inevitably cease.”

Unambiguously unconservative was the response of a New York mob a week after the Congress broke up. At dusk on November 1, 1765, the day the Stamp Act was to take effect, “A Wonderfull Large Mob” of sailors, youths, farmers, and blacks, along with “many people of substance,” began to form, armed with clubs and torches, and threatening to “bury” Royal Artillery Major Thomas James, who supposedly “had threatened to cram the stamps down their throats with the point of my sword.” Outside Fort George, where the first shipment of stamps lay under Lieutenant Governor Colden’s protection, the crowd hanged effigies of Colden and ex–prime minister Bute, before burning them in a bonfire, along with the outraged Colden’s cherished carriage of state. Then the rioters surged to Major James’s newly furnished house and despoiled it, frenziedly smashing fine furniture, mirrors, and paintings, slitting and shredding the mattresses and silk curtains, stealing the silver, trampling the garden, guzzling the wine, and smearing butter over what remained. At four in the morning, they straggled off. Jay’s father witnessed this “most surprising ferment on account of the stamp papers, and as violent attempts were intended to get them out of the Fort, I thought it most prudent for us to withdraw immediately to our more peaceable habitation in the country.” Rumors of mobs coming to “plunder the Town” swirled for the next week, and British commander in chief Thomas Gage warned Colden that if such a mob materialized and his men opened fire on it, “the consequence would . . . be an Insurrection” and “the Commencement of a Civil War.”

In this turbulent atmosphere—and rioting went on sporadically in the city of 18,000 for the next decade—John Jay came of age and worked out his view of the world and of himself. A week after the Stamp Act passed (but before the news reached America), he was still an adolescent, writing one of his few letters of this period, a passionate, unguarded avowal of friendship to Judge Livingston’s son, with an eager pleasure in young Robert’s having “opened wide those Doors of Friendship, into which I had long desired to enter” and looking forward to “our voyage to Eternity.” But after New York’s November riots, the city’s 30 or so lawyers suspended business because they refused to use the hated stamps required for legal documents (with unerring stupidity young George III and his apparatchik ministers had passed a radicalizing measure that fell hardest on America’s opinion-forming lawyers and journalists). Hence Jay had ample time to meditate upon the ferment seething around him. By the last year of his legal apprenticeship, 1768, everyone at the lawyer-dominated Debating Society Jay belonged to knew what one of the debaters meant (in a match Jay’s side won) when he spoke feelingly of “the Blessings of order and Tranquility and of the pernicious Consequences of Faction and Riot.”

Looking back on this period a decade later in a letter to Livingston—who had been his law partner from 1768 to 1770 and would go on to become chancellor of New York, secretary for foreign affairs, Jay’s unsuccessful opponent in the gubernatorial election of 1798, negotiator of the Louisiana Purchase, and the backer of Robert Fulton’s steamboat enterprise—Jay mused on the vast changes he saw in himself. Back in ’65, he wrote, he was “ambitious,” “pertinacious,” filled with “Bashfulness and Pride,” as “sensible of Indignities” as Livingston but more “prone to sudden Resentment.” How right he was about the stiff-necked pride, a mixture of stubborn principle and hair-trigger defensiveness against an ever-present sense of threat. A few weeks before his college graduation, he got briefly suspended for ostentatiously refusing to snitch on a classmate and brandishing the college bylaws to show that no rule required him to do so. As a novice lawyer, he had all but challenged the colonial attorney general to a duel for conduct that “represents me in an insignificant Point of View,” and he even expressed willingness to duel with an aggrieved young man he’d turned down for membership in the fashionable dancing assembly he cochaired. But though in those days, he might have been formed more “for a college or a Village” than for “a citizen of the World,” he told Livingston, he had since developed the requisite worldly flexibility, vivacity, and control over his pride, his facial expression, and his passions.

Though he didn’t mention it, he’d gained one other quality he’d confessed to having lacked in 1765—an understanding of women. For in 1774, he married as splendid a wife as could be found: Robert’s second cousin, Sarah Van Brugh Livingston, who shines out from her vivid letters like all of Jane Austen’s winsome heroines rolled into one, with sense and sensibility to spare. Then 17 while her husband was 28, Sally was one of the so-called three graces, the witty, spunky, and beautiful daughters of lawyer William Livingston, long one of New York City’s foremost politicians and then governor of New Jersey. While representing his family’s princely Livingston Manor in the New York Legislature, he had founded the influential (and wonderfully named) Independent Reflector, in which he had argued as early as 1752 that governments rest on the “free consent of Mankind” and that “those who have cloathed [a king] with Authority have a Right to strip him of it, whenever he abuses it.” Of Sally, the urbane Gouverneur Morris bantered the year before her marriage, “Never was a Little Creature so admired (I speak seriously). . . . As to her Heart when in the Midst of her Admirers it singeth with Joy. . . . The rosy Fingers of Pleasure paint her Cheeks with double Crimson. . . . And so it will continue if the Whim does not take her to get in Love.” But the whim did take her, and as her sister Kitty wrote a few years later, “Mr. & Mrs. Jay can be unhappy no where. They love each other too well.”

When the couple returned from their wedding trip in late May, though, Jay found the world turned upside down. While he was gone, news had reached New York of the first of Parliament’s Intolerable Acts, closing Boston’s port in retaliation for December’s Boston Tea Party—of which New Yorkers had held their own version the week before the Jays’ wedding, dumping overboard the first cargo of East India tea to reach town. Jay, by now a leading lawyer earning £1,000 a year, found himself already named to a committee to correspond with the other colonies and decide what to do, a committee whose numbers, form, and name shifted over the next two years but that ended up running both the city and the entire province. The committee joined the call for a continental congress, to which Jay won election in July 1774.

Jay’s townsmen pegged this youngest of all the congressional delegates as a conservative; and certainly, when an overwrought Patrick Henry exclaimed at the Congress’s start that “Government is at an End. All distinctions are thrown out. . . . We are in a State of Nature,” Jay mildly retorted, “I cant yet think all Government is at an End. The Measure of Arbitrary power is not full, and I think it must run over, before We undertake to frame a new Constitution.” Let’s not get carried away and think “We came to frame an American constitution, instead of indeavouring to correct the faults in an old one.” A reasonable remonstrance to Britain, Jay hoped, coupled with a determined trade boycott, ought to bring the ministry to its senses. Jay’s conservatism consisted only in this: that he would omit no effort—consistent with the rights of man and of Englishmen—to avoid an irreparable breach.

Assigned to write Congress’s “Address to the People of Great Britain,” Jay explained what those rights were. There’s no reason “why English subjects, who live three thousand miles from the royal palace, should enjoy less liberty than those who are three hundred miles distant from it,” he declared. “No power on earth has a right to take our property from us without our consent” or our “inestimable right of trial by jury,” as Britain has done in setting up admiralty courts, in which “a single man, a creature of the crown,” sits in judgment in tax-evasion cases on defendants presumed guilty until they prove their innocence. If Britons allow such injustices to befall their American cousins, they should keep two things in mind, Jay cautioned. First, “we will never submit to be hewers of wood or drawers of water for any ministry or nation in the world.” Second, “take care that you do not fall into the pit that is preparing for us.” Still, even after the king ignored Congress’s first petition, even after Concord and Lexington, Jay pressed for one last-ditch try in the Second Continental Congress, John Dickinson’s fruitless July 1775 “Olive Branch Petition,” some of whose language Jay supplied. But he remained realistic: in expressing his hope for an enduring American union with Great Britain, he conceded, “God knows how the Contest will end.”

More realistically still, while Congress was extending its olive branch with one hand, it was gathering up arrows with the other. In May 1775, in response to rumors that Britain was readying troops to enforce its will and might land them in New York, Congress advised New Yorkers “to persevere the more vigorously in preparing for their defence, as it is very uncertain whether the . . . conciliatory Measures will be successful.” In June, Congress began to raise an army and named George Washington its chief, two days before the Battle of Bunker Hill showed the British that they faced an unexpectedly hard war. Passing through New York when news of the fierce fighting arrived, the new commander, realizing that the politically divided colony’s royal governor, William Tryon, would probably start arming the loyalists, issued his first official order—to arrest Tryon if he did.

Both the rumors of invasion and Washington’s instincts about the loyalists proved correct, and John Jay rushed to counter each threat. To prepare for the invasion, he had to deal with an unintended consequence of the trade boycott he had championed and helped enforce. Not only did the ban fail to stem England’s harshness, as planned, but it also kept the colonies from stockpiling war supplies they turned out to need desperately. By the time even reluctant rebels like Jay understood that “the Sword must decide the Controversy,” New Yorkers were reduced to stripping the lead out from between their windowpanes to cast into bullets, and melting down their brass door knockers and bronze church bells for cannon. Pathetically, until better weapons turned up, Jay sent from Philadelphia a well-designed spear for New York craftsmen to copy.

After the new British commander in chief, Sir William Howe, moved the strategic center of the war to New York, aiming to use its great harbor as the hub of naval operations and to take control of the Hudson River, cutting New England off from the rest of America and then conquering the colonies one by one, Jay went on a wild ride through Connecticut, rounding up cannon from the Salisbury foundry to defend the river and heavy chain to block the Royal Navy from sailing up it. But supplies—everything from bullets to blankets to boots—remained scarce for the entire war. “There have been instances, and I speak from the most undoubted authority,” wrote Jay in 1780, “of considerable detachments marching barefooted over rugged tracts of ice and snow, and marking the route they took by the blood that issued from their feet.”

As for the loyalists, New York was unique among the colonies in the strength of its residents’ attachment to the mother country; at least a third wholeheartedly supported the king and another third trimmed from side to side.

After the brothers Howe, general and admiral, sailed into New York Harbor on June 29, 1776, turning it into “a wood of pine trees” from the Lower Bay to the Tappan Zee with the masts of 82 warships—once the British occupied the city in September and kept it as a stronghold for the next seven years—the whole colony became a dragon-ridden theater of threat, fear, and violence. If John Jay had seen one kind of ferocious anarchy in the urban riots of 1765, when he watched men in a frenzy of murderous destructiveness, he lived through a different kind of anarchy, no less fearsome and instructive about human nature and its brutish capacity for evil, from 1776 to ’78.

Sitting on the cool veranda of his Westchester farmhouse before moving into his richly carpeted dining room, with its “JJ”-monogrammed Chinese-export dishes bought for his wedding, its table and 24 chairs of the finest and heaviest mahogany skillfully carved in the simplest, least pretentious late-eighteenth-century style, an elderly John Jay talked of these times one memorable evening to his son William’s boyhood schoolmate, James Fenimore Cooper, who became the new country’s first novelist. Two weeks before the British entered New York Harbor, New York’s Provincial Congress, of which Jay was a member while also a Continental Congressman, had assigned him to chair a committee to deal with fifth-columnists, and he evoked for his young friend Cooper the shadowy world of “plots, conspiracies, and chimeras dire” he would occupy for some time to come.

He found that Governor Tryon had indeed “been very mischievous,” raising a corps of New York’s British sympathizers to support the invading army when it arrived and funneling money to them through the city’s mayor. More alarmingly, he found that the plotters included a soldier of George Washington’s bodyguard, who, according to later rumor (never proved), plotted to kill the general. The mayor went to jail, the guardsman to the gallows.

What Cooper remembered from that long evening’s talk was Jay’s description of how, as head of the Committee for Detecting Conspiracies, he had run a spy ring in Westchester and the Hudson Valley once the British had occupied Manhattan, Staten Island, and all of Long Island, a tale Cooper elaborated in 1821 into the very first best-selling American novel, The Spy. With the Royal Navy commanding Long Island Sound and part of the Hudson, and the British army driving Washington’s small, ill-equipped force across New Jersey, politically divided Westchester, Cooper recounts, “had many of the features of a civil war,” with the British invaders “profiting by these internal dissentions” by arming troops of loyalist auxiliaries “to reduce the young republic to subjection.” The Americans formed their own troops of irregulars in response, for “annoying the enemy,” who had regular, as well as ragtag, troops in the county. Both guerrilla groups, the patriot “Skinners” and the loyalist “Cow-Boys,” tended to degenerate into savage and pitiless marauders—roving “banditti of ruffians” (as Tom Paine described the State of Nature’s primal hordes)—“whose sole occupation appears to have been that of relieving their fellow-citizens from any little excess of temporal prosperity they might be thought to enjoy,” as happened to John Jay’s father and siblings, leaving them only their clothes and their lives. They were lucky, though, as this gang of Cow-Boys murdered some of their other victims.

“Oppression and injustice” reigned, says Cooper. “The law was momentarily extinct in that particular district, and justice was administered subject to the bias of personal interests and the passions of the strongest.” The locals lived in doubt and fear of predators, often too demoralized to plant crops, distrustful of their neighbors, and hiding their real sympathies—if they had them. Patrick Henry was wrong in saying that America had returned to the State of Nature in 1774, but in Westchester in the late 1770s, it was Thomas Hobbes’s war of all against all—a laboratory demonstration for political philosophers and a graduate education for John Jay.

Though Jay never named him, he told Cooper the story of one of his spies, Enoch Crosby, whose 1832 deposition requesting a federal pension recounts adventures much like those of Cooper’s hero, Harvey Birch. A virtuoso of deception and double-dealing, brave, cool, resourceful, and patriotic, Crosby, surviving hair-raisingly narrow escapes, helped American troops capture some 100 recruits to the British forces, some loyalist by conviction, some opportunistic freebooters.

Once elected chief justice of New York in May 1777, Jay remained knee-deep in such banditti. “I am now engaged in the most disagreeable part of my duty—trying criminals,” he wrote Gouverneur Morris in the spring of 1778. “The Woods afford them Shelter and the Tories Food. Punishments must of course become certain, and Mercy dormant, a harsh System repugnant to my Feelings, but nevertheless necessary.” He had before his court in Albany a gang of Cow-Boys who’d looted two Columbia County farms, killing the son of one farmer, a Continental soldier home on leave. They were “tory criminals,” according to the New-York Journal, bandits and traitors rolled into one. “Their thefts and robberies they justified, under the pretense of the goods being lawful prizes, forfeited to the King.” Jay sentenced ten of them to hang.

Anyone who wants to keep his hands clean and his conscience pure had better not choose politics as a vocation, Max Weber famously wrote, because politics operates through “power backed up by violence,” and its guiding principle—the very opposite of the Christian command to “Resist not him that is evil with force”—is “ ‘Thou shalt resist evil by force,’ or else you are responsible for the evil’s winning out.” But here one enters a moral morass, for “he who lets himself in for politics, that is, for power and force as means, contracts with diabolical powers, and for his action it is not true that good can follow only from good and evil only from evil, but that often the opposite is true.” John Jay came to understand this ethical dilemma with all his being once he began detecting conspiracies. For if it’s disagreeable enough to hang men for their heinous actions, what about jailing or banishing people from their homes on suspicion—on information from spies about their political beliefs, or on their refusal to take loyalty oaths? Should people be punished not just for their action but also for their inaction? For their beliefs?

As early as November 1775, Jay answered by proposing harsh measures when Congress asked him how to handle disaffection in Queens County on Long Island, which declared itself neutral in the looming conflict and voted not to send delegates to Philadelphia. It’s not acceptable to be “inactive spectators,” Jay declared, hoping, if the British win, “to purchase their favour and mercy at an easy rate,” while, if America wins, “they may enjoy, without expense of blood or treasure, all the blessings resulting from that liberty which they, in the day of trial, had abandoned.” Accordingly, he recommended that the declared neutrals “be put out of the protection of the United Colonies,” confined to their county, excluded from the law courts, and disarmed by New Jersey and Connecticut troops.

Some who claimed neutrality, Jay suspected, were actively supporting the enemy by “collecting and transmitting intelligence, raising false reports, and spreading calumnies of public men and measures.” Or worse, as he found when Beverley Robinson, a prosperous merchant related to his mother, came before his committee in February 1777. “Sir we have passed the Rubicon and it is now necessary every man Take his part,” Jay told Robinson. “Cast off all alliegiance to the King of Great Britain and take an oath of Alliegiance to the states of America or Go over to the enemy for we have Declared our Selves Independent.” This was an age, remember, when giving your word or swearing in God’s name put your honor or your soul at stake. Replied Robinson, “Sir I cannot Take the Oath but should be exceeding Glad to Stay in the Country.” Think it over, Jay advised. Jay wrote Robinson’s wife, urging her to persuade him to take the loyalty oath. But by then, Robinson had started to raise a loyalist regiment; and by March, Jay got news that he’d guided British regulars to attack American soldiers at Peekskill, wounding two.

But some of the neutrals were neither traitors, liars, nor trimmers, and Jay faced no harder case than that of his honorable King’s College friend Peter Van Schaack, who “condemned the conduct of the Home government” in London, Van Schaack’s son reported, but “was yet opposed to taking up arms in opposition to it” and felt conscience-bound not to take the loyalty oath against his king. Jay directed him to appear before the Albany authorities, whose proceedings led to his ultimate banishment to London, from which he wrote Jay in 1782, as the Revolution was drawing to a close, tentatively hoping to reopen communication. Jay replied at once: “I have adhered to certain fixed Principles, . . . without regarding the Consequences of such Conduct to my Friends, my Family, or myself; all of whom, however dreadful the Thought, I have ever been ready to sacrifice, if necessary, to the public Objects in Contest. Believe me, . . . I felt very sensibly for you and for others; but as Society can regard only the political Propriety of Men’s Conduct, and not the moral Propriety of their Motives to it, I could only lament your unavoidably becoming classed with many whose morality was convenience. . . . No one can serve two Masters: either Britain was right, and America wrong; or America was right, and Britain wrong. . . . Hence it became our Duty to take one Side or the other.” He closes by asking how his old friend and his children are doing. “While I have a Loaf, you and they may freely partake of it. Don’t let this Idea hurt you. If your Circumstances are easy, I rejoice; if not, let me take off their rougher Edges.”

Van Schaack wrote back with equal magnanimity: “Be assured, that were I arraigned at the bar, and you my judge, I should expect to stand or fall only by the merits of my cause.” He had reasons for his choice, he continued. “Even in a doubtful case, I would rather be the patient sufferer, than run the risk of being the active aggressor.” But now that the fighting is over, “if America is happier for the revolution, I declare solemnly that I shall rejoice that the side I was on was the unsuccessful one. . . . I have always considered you as one of the foremost enemies of this country, but since what has happened, has happened, there is no man to whom I more cordially wish the glory of the achievement.” As for his children, his son has been accepted at Yale. In time, Van Schaack returned to his New York law practice, and the friendship bloomed again.

Loyalty oaths, wartime un-American-activities committees: William Jay asserts that, while his father “was ever ready to adopt all proper measures for preventing the tories from injuring the American cause, he abhorred the idea of punishing them for their opinions.” Not so. He believed America was in a fight for its existence against enemies who, as he wrote to his fellow New Yorkers, “plunder your houses; ravish your wives and daughters; strip your infant children; expose whole families naked, miserable and forlorn, to want, to hunger, to inclement skies, and wretched deaths”; and who seek to impose a slavery such as “Egypt, Babylon, Syria, or Rome” imposed upon the Jews—or as Catholics, he might have said, imposed on Huguenots. The greatest sin and dishonor would be not to fight to win, whatever it took. A life-or-death struggle has no margin for error.

Along with these indelible lessons in anarchy, Jay learned five great lessons about anarchy’s antidote—government—in his education as a statesman during his presidency of the Continental Congress from December 1778 through September 1779. First, he grasped that American unity was permanent. Our enemies, he wrote in his “Circular Letter from Congress to their Constituents,” argue “that the confederation of the States remains to be perfected; that the union may be dissolved.” They are wrong. “These states are now as fully, legally, and absolutely confederated as it is possible for them to be.” The ongoing war is making the bond ever stronger. “A sense of common permanent interest, mutual affection (having been brethren in affliction), the ties of consanguinity daily extending, constant reciprocity of good offices, . . . all conspire in forming a strong chain of connexion, which must for ever bind us together.” Jay welcomed every sign of growing unity. He cheered the marriages of two fellow congressmen to ladies from states not their own: “I am pleased with these intermarriages,” he wrote John Adams. “They tend to assimilate the States and to promote one of the first wishes of my Heart viz. to see the People of America become one nation in every Respect.” And he objected to Massachusetts’s description of itself “as being in New England as well as in America. Perhaps it wd. be better if these Distinctions were permitted to die away.”

Second, a Federalist by instinct even before there was Federalism, he understood that union required a strong central government sovereign over the states. As early as October 1775, he wrote: “The Union depends much upon breaking down provincial Conventions.” Accordingly, during his presidency, Congress for the first time—and in his handwriting—declared its supremacy over the state governments, overturning a Pennsylvania statute (and a Pennsylvania jury decision) in the allocation of the sloop Active as a war prize. “Congress,” Jay pronounced in taking these actions, “is by these United States invested with the supreme sovereign power of war and peace.”

Third, assuming the presidency when the quarrel between two top American diplomats, Silas Deane and Arthur Lee, had reached its apogee of bitterness, with murky charges of malfeasance and spying flung about in Congress, Jay learned a wariness toward his own colleagues. “There is as much intrigue in this State House as in the Vatican,” he commented, “but as little secrecy as in a boarding School.” His distrust only deepened when General Horatio Gates, part of a cabal of senior officers seeking to displace George Washington as commander in chief, sent him an insinuating letter critical of Washington’s military strategy. Rightly judging the letter mere Machiavellian self-serving on Gates’s part, like so much of the unprincipled self-interest he had seen in Congress, Jay sent Washington the relevant passage as a heads-up and received in response a letter of such nobility of character and comprehensive strategic and managerial brilliance as to teach him his fourth great lesson: that Washington was a world-historical leader. The two became friends and confidants; within weeks, Washington moved from signing himself “Yr. obliged & obed. Ser.”

to “Yr. most obed. & affect. Servt.,” though it took Jay six months to get up the nerve to tell the “master-builder” (as he termed the great man) that “with sincere affection & Esteem, I am your friend & servant.”

The fifth lesson proved the most useful of all to the man who set the future course of U.S. foreign policy: in the world of diplomacy, nothing is what it seems, so trust no one. He entered that murky world in November 1775, well before the colonies declared independence, when Congress sent him, Benjamin Franklin, and Thomas Jefferson to see a nameless Frenchman who’d requested a secret meeting in Philadelphia. As William Jay remembers his father often recounting, the elderly, lame man stated that the king of France, then officially at peace with George III, favored the colonists’ defense of their rights and wished to help with arms and money. When the trio repeatedly asked by what authority he spoke, the man merely drew his hand across his throat and replied, “Gentlemen, I shall take care of my head.” Shortly thereafter, Congress—impressed by this drama, Jay thought—appointed him to a secret committee to seek aid from abroad.

A year later, after further foreign encouragement, the committee sent Silas Deane to France, posing as a merchant, to obtain the promised arms and supplies, which France furnished through a front company to hide its role. One of Arthur Lee’s accusations in the Deane-Lee catfight raging in Congress when John Jay assumed its presidency was that Deane had charged Congress for matériel that France had given as a gift. When Tom Paine, secretary to Congress’s Committee for Foreign Affairs, leaked in the press the secret information that France had most certainly given such a free gift, French ambassador Conrad Gérard, to preserve the fiction that France had not aided America while still at peace with Britain, demanded that Congress refute what he claimed was a calumny against “the Dignity and the Reputation of the King my Master”—even though by then, France, convinced by the American victory at Saratoga in October 1777 that the rebels could win, had signed a formal alliance with the United States in February 1778. So John Jay, in one of his first acts as president, had to call Paine before the bar of Congress to discipline him for telling the truth. Sacrificial whistle-blower Paine resigned in outrage before Jay could fire him.

During Jay’s nine months as president, Ambassador Gérard “used frequently to spend an evening with me,” Jay wrote, “and sometimes sat up very late,” urging on Jay the wisdom of drawing Spain into the war as an ally, and outlining the inducements America might offer. Gérard made the same argument to Congress, which in late September 1779 named Jay minister plenipotentiary to Spain, with instructions to seek such an alliance.

So sudden was the appointment that Jay could say good-bye to his family only by letter—as could his wife, who, as sharp an observer of the era and as sparkling a writer as Abigail Adams, had with utter unconventionality decided to go with him. “Considering the mortality of man, and my time of life,” Sally’s loving father wrote her, “it is probable I may never see you again. O may God Almighty keep you in his holy Protection, & if it should please him to take you out of this World, receive you into a better!”

That very nearly happened. Eighteen days out of Philadelphia, their 185-foot frigate sailed into a savage winter gale that tore away her masts and bowsprit and damaged her rudder. The falling spars had injured two sailors, Sally told her mother in a long and typically vivid letter; one, “poor fellow! surviv’d not many days the amputation of his arm.” By no possibility could the jury-rigged ship reach Europe, her officers concluded, though Gérard, who was on board, demanded that they continue eastward. Jay, in his first diplomatic negotiation, got the ambassador to agree to head south to Martinique with “the first fair wind that offered (which was not ’till near three weeks from the above mentioned aera),” Sally wrote. She marveled at her husband’s “firmness & serenity of mind.” “Your whole family love Mr. Jay, but you are not acquainted with half his worth,” she told her mother, “for his modesty is equal to his merit. It is the property of a Diamond (I’ve been told) to appear most brilliant in the dark; and surely a good man never shines to greater advantage than the gloomy hour of adversity.” Now, wrote Sally, as the frigate rolled and fellow passengers played checkers at her cramped table, she is dreaming of Martinique’s fruit. A few days later, she added, “A land bird! A land bird! Oh! the pleasure of being near land!”

Ashore, she set off to explore the exotic island, where it seemed “in a sportive humour [nature] had display’d a whimsical fancy” and which she described to Governor Livingston with characteristic verve and economy. She always noticed and praised landscapes cultivated and improved by labor. “It is really surprising to trace the effects of industry on the very summits of the hills which are covered with coffee, coconuts, and cane,” she remarked, and went on to describe, with her lifelong delight in how things work, the island town’s ingenious plumbing system. To her father-in-law, once the Jays had left Martinique and were “sweetly sailing before the wind” toward Europe, she wrote two observant paragraphs describing with crisp precision how a sugar mill turns cane into sugar and molasses.

Though Jay didn’t know it, his mission to Spain was doomed from the start. With a colonial empire in the New World, the Spanish king, who had his own imperial ambitions in North America that competed with American claims, shuddered at the idea of colonial rebellion and would never officially support one, even to harass Britain. Making matters worse, Spain and France were conspiring behind America’s back. While Congress dithered about whom to send abroad, the two Bourbon powers secretly revived their decades-old Family Compact in the Treaty of Aranjuez, which bound Spain to join the war against Britain in exchange for France’s pledge not to make peace until the Spanish got Gibraltar back—a deal that not only ignored America’s claims but also violated France’s treaty with America by its clandestine change in the peace requirements. Also unfriendly to America was France’s agreement to let Spain share the Grand Banks fishery, long an American fishing ground, if France could win it. And there was one more thing Jay didn’t know: though Spain had helped America with money and supplies early in the Revolution, now that she was herself at war, she had no money to spare, despite the legends about her wealth.

Jay might have figured out the economic truth beneath the facade early on. The first leg of his trip from Cádiz, where he landed in January 1780, to Madrid, was pure pomp, with 16 or 20 oarsmen rowing “a very handsome Barge . . . ornamented by a crimson damask canopy handsomly fringed,” Sally wrote in one of her letters, which provide the best account of the Jays’ day-to-day life in Europe. But soon the travelers transferred to something “they’ve the impudence to call . . . Coaches, it’s true they are made of wood and have four wheels, but there the resemblance ceases.” As for the inns, “the awkwardness and filth of every thing exceed description. . . . The very first evening we found that a broom was absolutely essential,” for sweeping out “several loads of dirt in which were contain’d not [less] than two or 3000 fleas, lice, buggs, &c. if we may form any Judgment by what still remained.” To add insult to injury, her husband wrote, the landlord charged their party of eight for the 14 beds in their rooms, observing “that we might have used them all if we pleased.” Hardly signs of a rich country.

For the two and a half years of “this honorable Exile,” as he called it, Jay fruitlessly trailed after the Spanish court as it accompanied the king from palace to palace. Given his paltry salary, Jay wrote, “To keep a House at each place is not within the Limits of my Finances.” Even hiring mules and a chaise to follow the court strained his budget. “So circumstanced I cannot employ Couriers to carry my Dispatches to the Sea Side or to France. My Letters by the Post are all opened”—and indeed the Spanish secretary of state once handed over a top-secret letter that Congress had sent Jay, without bothering to conceal that he’d intercepted and read it. Living in furnished single rooms with one servant, Jay had to leave Sally, his invaluable source of moral support, in Madrid, where, as the court had never recognized him as an ambassador, she knew almost no one. When a daughter was born in July 1780, Sally’s “whole heart overflowed with Joy & gratitude.” But the baby died three weeks later. “Excuse my tears,” Sally wrote—“you too mamma have wept on similar occasions, maternal tenderness causes them to flow & reason, tho’ it moderates distress, cannot intirely restrain our grief, nor do I think it should be wish’d.”

Jay’s financial problems weren’t just domestic. In its desperation for funds, Congress began spending the money it hoped he could raise from Spain, drawing bills of exchange on him for £200,000 (these typical financial instruments of the time order a second person—Jay—to pay a supplier or lender a specified amount by a given date). Though at first, Spain’s minister of state, the count of Floridablanca, came up with funds when pressing bills came due, and hinted further help, the flow trickled off, the count temporized, and Benjamin Franklin, America’s ambassador to France, had to raise money there to pay the bills as well as Jay’s salary. continue….