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Basking Ridge, Lord Stirling’s country house near Elizabeth, New Jersey, offered a gathering place where his aides mingled with fellow officers and polite society. Stirling’s wife, Sarah, was a Livingston and her brother William was the governor of New Jersey. The Stirlings and the Livingstons, and their friends and guests, added social distinction to the wartime experiences that widened Monroe’s vision of the new nation while shaping his impressions of other American states and their rising leaders. Major Monroe was close at hand when Major James Wilkinson brought news of the victory at Saratoga and then schemed with the Conway Cabal to supplant Washington as commander in chief. Monroe enjoyed the counsel of Mrs. Theodosia Prevost, the future wife of Aaron Burr, as he extricated himself from a sentimental
affaire de coeur
with a young lady he met at the Hermitage, the Prevost mansion in Paramus, New Jersey. As one of the few American staff officers who spoke a little French, Major Monroe became well acquainted with the marquis de Lafayette, who spoke a little English.

When the war moved into the Carolinas, Monroe followed eagerly, bearing a letter of recommendation from Washington “as a brave, active, and sensible officer.” Washington’s aide Alexander Hamilton offered more exuberant praise: “Monroe is just setting out from Head Quarters,” Hamilton advised Henry Laurens, of South Carolina,

and proposes to go in quest of adventures to the Southward. He seems to be as much of a knight errant as your worship, but as he is an honest fellow, I shall be glad he may find some employment, that will enable him to be knocked in the head in an honorable way…. You know him to be a man of honor a sensible man and a soldier. This makes it unnecessary [for] me to say anything to interest your friendship for him. You love your country too and he has the zeal and capacity to serve it.

Appointed minister to France in 1794 by President George Washington, James Monroe (opposite page) purchased an elegant house on the rue de Clichy, near Montmartre. There in 1796 he and Elizabeth Kortright Monroe (above) sat for watercolor-on-ivory portraits by the Swiss-born miniaturist Louis Sené. Devotees of French fashion, as were many American republicans, the Monroes resided twice in Europe

in Paris from 1794 to 1797 and in Paris and London from 1803 to 1807—and they brought their taste for elegant French furniture, fashion, and cuisine to the decor of the White House in 1817.
(James Monroe courtesy James Monroe Museum and Memorial Library, Fredericksburg, Virginia. Elizabeth Kortright Monroe courtesy Ash Lawn-Highland, Charlottesville, Virginia.)

Sarah Vaughan, Kitty Livingston, and their circle sensed that Monroe was well-read. Perhaps they knew that he had read law with Thomas Jefferson after the war and opened a law office in Fredericksburg, at the falls of the Rappahannock River, before entering politics. Miss Vaughan had doubts about Monroe’s “gaiety and liveliness” and was undecided about whether he was handsome. Her friend Kitty Livingston could decide whether the tall young Virginians deeply dimpled chin “constitutes beauty.” Clearly, whatever his other merits, James Monroe was sensible. Sarah Vaughan and Alexander Hamilton were in agreement on that—as was George Washington, the American paragon of good sense.
3

Sensible and serious, James Monroe rose quickly in Virginia politics. He started in 1782 with a seat in the state legislature vacated when his uncle
and patron, Joseph Jones, went to Congress. He was soon appointed to the executive council along with the future chief justice John Marshall and Jefferson’s diplomatic protégé William Short. In an age skeptical of executive power, this council advised the governor and served the commonwealth as a political training ground where promising young men on the way up rubbed elbows with seasoned politicians on their way to retirement. The next summer, Monroe’s diligence gained him election to Congress.

As a congressman during the 1780s, Monroe and his colleagues were as much diplomats as legislators, for the Confederation Congress resembled the General Assembly of the United Nations more than its modern congressional namesake. A prominent Massachusetts congressman called his delegation “our Embassy” and hoped its conduct would “merit the Approbation of our Country”—by which he meant his state. Another “mere freshman” from Connecticut described Congress as “a maze, a
labyrinth of which I have not yet got hold of the clue. Some business is done in Congress, some in committee and boards. I am labouring to explore these different powers and provinces, but make very slow progress.”
4

Constitutional restrictions, chronic poverty, and habitual absenteeism put the national government in a tight harness. The state legislatures generally chose the members of Congress, and kept them reined in with detailed instructions—all to ensure that political power stayed in the states and localities. Not surprisingly, after independence had been won, many states sent the second string to Congress while their best men stayed at home. “The members of Congress are no longer, generally speaking, men of worth or of distinction,” one congressman told a Dutch visitor, “for Congress is not, as formerly, held in respect… [and] the governments] of the States and the foreign missions absorb the men of first rank in the Union.” As the largest and most populous state in the Confederation, Virginia generally sent a delegation to Congress that was a cut above the others. Like the state’s executive council, the Virginia congressional delegation always included a few seasoned leaders, a couple of promising youngsters sent to test their wings, and some second-stringers to hold down the bench while the others were on the floor or in committee. The fact that Virginia paid its delegates on a per diem basis probably helped, too. Congressmen from some states had fewer incentives for diligence, and they often had difficulty getting paid at all.
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Unlike John Francis Mercer, whose outrageous opinions and “great swelling words” prompted a wintry puritan from New Hampshire to give thanks when the “Prince of the South” retired from Congress, Monroe stood out among Virginia’s young men (as would James Madison when his turn came).
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The leaders of his delegation included Monroe’s wise old cousin William Grayson, whose intellect and wit enlivened many a debate, the proud aristocratic Richard Henry Lee, and, before Jefferson left for his diplomatic mission to France, the author of the Declaration of Independence. Among the middling talents were Edward Carrington from Cumberland, Samuel Hardy from Isle of Wight, and Richard Henry Lee’s irascible younger brother Arthur. The Lee brothers sometimes stood aloof from the rest, but on the whole the Virginians acted together and exercised influence well beyond their numbers.

Fashionable Sarah Vaughan may have doubted the dimpled young bachelor’s “gaiety and liveliness,” but Congressman Monroe was sensible, attentive, and hardworking. Aboard a sloop in the Hudson River, these character traits may not have swept stylish young ladies off their feet, but when the question of the future of the Mississippi River threw the Confederation
Congress into turmoil, Monroe’s steady intelligence, keen ear, and diligent attendance proved their worth.

Monroe’s second year in Congress ended calmly enough. “There seems in Congress an earnest disposition to wind up our aff[ai]rs as they respect foreign nations,” Monroe assured Thomas Jefferson in June 1785. “I have never seen a body of men collected in which there was less party, for there is not the shadow of it here”—a situation that soon changed drastically.
7
That spring Congress had witnessed some disagreements about how to sell land in the Ohio Country. Acting on advice from Massachusetts politician Timothy Pickering, Congressman Rufus King had introduced legislation requiring the sale of western lands in tracts no smaller than thirty thousand acres (a policy that favored land companies and wealthy speculators), while Monroe, Grayson, and others sought to allow the sale of the land in more affordable squares of six hundred forty acres. In the end, “all parties who have advocated particular modes of disposing of this western territory have relinquished some things they wished,” said Rufus King, “and the ordinance is a compromise of opinions.” The result of that compromise was the Land Ordinance of 1785. “It is not the best in the world,” William Grayson declared as he sent a copy to James Madison, but “it is I am confident the best that could be procured for the present.”
8

The Land Ordinance of 1785 gave birth to the straight country roads, right-angle intersections, and rectangular fields that modern travelers take for granted as they fly across the tamed and cultivated expanse of Ohio, Indiana, Illinois, Michigan, and Wisconsin. Upon the ancient forests of the Old Northwest, it branded a grid announcing the arrival of civilization and the Age of Reason. In time these straight lines and right angles, which Thomas Jefferson had first introduced in earlier legislation about western lands, projected American notions of order across the vast unruly landscape of the Louisiana Purchase, too, from the Ohio River to the Rocky Mountains.

While Congress found its way to an amicable compromise over western land policy, Monroe and his colleagues awaited with some trepidation the arrival from Madrid of Carlos Ill’s newly appointed negotiator, forty-nine-year-old Don Diego de Gardoqui. Days after learning that Gardoqui was en route to the new republic, Richard Henry Lee alerted George Washington that he “apprehend[ed] a very firm ostensible demand from him, of the exclusive navigation of the Mississippi.” Lee speculated hopefully that Gardoqui’s “secret orders touching an ulterior agreement may be another thing,” and he concluded that

Time and wise negotiation will unfold this very important matter, and I hope secure to the U.S. and those Individual states concerned, the great advantages that will be derived from a free navigation of that river.
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Officially, Congress assured the Spanish court that it would welcome Gardoqui to New York City with “all the Distinction and Respect which the Dignity of his Sovereign and the Nature of his Commission may demand.” As to “the great Business he is sent to negocíate with the United States,” Congress promised that the negotiations “shall be conducted on their part with the greatest Candor and Frankness.”
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Fair words—but these congressmen knew that the art of diplomacy is not always candid or frank. Ambassadors, in the famous remark of an English diplomat who witnessed his countrymen settling at Jamestown and Plymouth, are honest men sent abroad to lie for their country.

Diego de Gardoqui y Arriquivar was an experienced diplomat. He left a position as head of Spain’s consular service in London to accept the assignment in New York City, where Congress regularly met at the time. Born in Bilbao, on the Bay of Biscay in the Basque country north of Madrid, Gardoqui had studied in London for several years. He spoke impeccable English and had grown up around British and American merchants doing business with his father, José Gardoqui. The son had demonstrated his talents in a series of local appointments when Carlos III summoned the thirty-one-year-old businessman to court on the eve of the American Revolution. Within weeks he found himself in the middle of Spain’s effort to help the American colonies without openly offending Great Britain—a task made more difficult by the appointment of the contentious Arthur Lee as one of America’s agents on the Continent. A bull in the china shop of European diplomacy, Lee was based in Paris and the Spanish wanted him to stay there. When Lee set out for Madrid, Gardoqui deftly intercepted him—at Pamplona no less—and soon emerged as Carlos Ill’s expert on all things American. Through his father’s firm, Gardoqui and Sons, Spain covertly shipped thousands of dollars’ worth of Spanish goods and materiel to the American army, and the port of Bilbao became a haven for American privateers.
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When Congress sent John Jay to Madrid seeking official Spanish recognition and a treaty of alliance, Gardoqui was the intermediary between Jay and José Moñino y Redondo, count of Floridablanca, chief minister to the king from 1780 to 1792. After the war, Gardoqui was the
natural choice when Carlos decided to send a negotiator to the new American republic. He knew the strengths and situation of the American people. He knew the importance of the Mississippi River, the details of Spanish-American trade, and the predilections of many American leaders—and some of their wives.

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