In the summer of 1787, as the Constitutional Convention took place in Philadelphia, General James Wilkinson journeyed to New Orleans to visit Spanish Governor Esteban Miró, ostensibly about obtaining a monopoly on trade down the Mississippi River from Kentucky. Wilkinson brought with him flour, butter, bacon, and tobacco—examples of the goods he said he hoped to trade—but it was all just a cover for what he really wanted to discuss: removing the region of Kentucky from the United States to join the Spanish Empire as a new colony. During that trip, Wilkinson enlisted in the Spanish cause and agreed to be a spy for them while serving in the United States Army. On August 21, 1787, Wilkinson presented his plan to Governor Miró.

The general was confident of success. He believed free access to the Mississippi would persuade many in Kentucky to pledge allegiance to a new flag. Their loyalty would follow their crops to Spanish New Orleans. Still, Wilkinson explained, it would help to pay off several notable men of Kentucky. If “Spain can attach to her, the influential Characters among the Western Americans,” Wilkinson argued, “then they [will be] able to accomplish their separation from the United States.” Wilkinson had in mind men such as Virginia Attorney General Harry Innes, Congressman John Brown, Judge Caleb Wallace, Revolutionary War veteran Isaac Shelby, Commodore Richard Taylor, and Colonel Henry Lee.

Wilkinson’s plot never came to fruition. Some of the leaders he targeted, such as Taylor and Lee, only wanted to break Kentucky away from Virginia, of which it is was still a part, not join a new country, while others thought the new Constitution should be given a chance before making a permanent separation. Wilkinson found his dealings with the Spanish scrutinized. One official reported to President George Washington that “a violent separation from the United States seems to be laid down as the groundwork which ever other consequence depends.” And yet Wilkinson’s so-called Spanish Conspiracy did not ruin his reputation. Rumors circulated, but Wilkinson was careful to conceal his true intentions and went on to enjoy a long career in the U.S. Army, maintaining the trust of multiple presidents.

What does the existence of a man like Wilkinson say about the new American nation? How could he have worked against US interests while so brazenly advancing his own—and gotten away with it? Certainly, Wilkinson was skilled in the arts of deception, but he was hardly unique in the early United States. Untold numbers of men saw opportunity in the new nation—opportunity to serve themselves regardless of what the official culture said about public virtue and self sacrifice as the lifeblood of a republic.

After all, the country was unstable at best under the Articles of Confederation, and even after it went into effect, little was known about the untested Federal Constitution. Many people doubted its strength and longevity, including the Spanish and British who believed that with correct nudging they could induce the young nation into chaos. Revolutionary America (1776–1815) was a time of fluid national identity, when attachments to the nation competed with local, regional, and state affiliations. Into the uncertain political and commercial environment stepped self-interested men who saw their chance to improve their social status, fatten their pocketbooks, and burnish their legacies. Although, like Wilkinson, their plans often failed, their actions ultimately determined how the young United States of America matured.

Today, the term “scoundrel” seems either archaic—the kind of thing wig-wearing gentlemen called each other before taking up dueling pistols—or something from the realm of fantasy, a way to describe Han Solo from the Star Wars universe. (A scoundrel definitely shoots first.) In reality, “scoundrel” was a meaningful term in the Revolutionary era. Samuel Johnson’s 1755 dictionary, for example, defined scoundrel as “a mean rascal; a low petty villain.” That definition implies a lot of potential meanings, and in common usage the term was certainly flexible. Some men were considered scoundrels because of their unethical commercial activities. Others because of their political schemes. Still others were labeled “scoundrels” because of the way they violated international boundaries. Some were simply criminals.

The present work reveals the many ways to be a scoundrel in the Revolutionary period. Perhaps the most extreme way to earn the name was to do something which might be considered treason. To many Americans, there was no man more treasonous than Benedict Arnold. With his defection to the British Army in 1780, Arnold immediately became one of the most hated men for American patriots, erased all the heroic deeds he had previously performed on the battlefield, and forever tarnished his legacy. Aaron Burr, too, has a scandalous reputation. Though his legacy in popular culture is mostly tied to killing Alexander Hamilton, Burr was also accused of treason, standing trial for his escapades in the West which involved plans for filibustering in Mexico, waging a war against Spain, creating an independent government, launching a coup, or starting a civil war. Burr was a former vice president and popular among his followers. His scheming rocked the young republic. Other men’s involvement with foreign powers was more hidden but still raised suspicions. James Wilkinson’s treachery was not known until after his death in 1825, but throughout his life his rivals always suspected his treason. Yet he rose to be the highest ranking general in the army. One of Wilkinson’s protégés, Philip Nolan, was also suspected of being in league with the Spanish. Over time, Nolan went from being a horse trader in Central Texas to Spanish informant to an untrustworthy American, which led to his murder in 1801.

Another extreme way to be remembered as a scoundrel was to commit murder. That’s how Jason Fairbanks of Dedham, Massachusetts, gained infamy in 1801: as the killer of his would-be love, Elizabeth Fales. Early nineteenth-century America was a violent place, but the murder and Fairbanks’s trial were the talk of New England because the story was about more than love gone wrong. Fairbanks’s obsession with virtue and reputation drove him, paradoxically, to become a scoundrel and damage his family’s legacy, a warning for a nation with a public culture similarly obsessed with virtue and reputation.

Other figures profiled in the pages that follow looked west and south and found ample opportunities for taking advantage of others. Located on the border with Spanish territory and far from the seat of the US government, the American West and the Gulf South were often an international playground for schemers who sought to make a fortune or even to carve out their own empire. William Blount, Thomas Green, and the Kemper brothers—Reuben, Nathan, and Samuel—sought ways to line their own pockets by taking advantage of their situations and positions in society. The moral flexibility of these men leaned toward their economic favor regardless of the ethics or legality of the activity. William Blount of Tennessee, for example, was a crooked senator and land speculator. He became the first person impeached in the newly formed federal government because he openly used his position to increase the value of his real estate. He was also crucial to the development of early Tennessee. Thomas Green attempted to launch an unauthorized private military attack, called a filibuster, against Spanish Natchez on behalf of the state of Georgia. Green’s actions forced the national governments of the United States and Spain to take notice of the backcountry region of Natchez and the lower Mississippi River. He showed that self-serving men could dictate the policies of the nation because there really was not anything stopping them, as the Articles of Confederation were weak and ineffective. The Kemper brothers turned a personal vendetta against Spanish officials in West Florida into a bid for the region’s independence. Unlike the Kempers, however, many Americans living in Spanish West Florida were happy under a foreign government. It worked for them. But the Kempers wouldn’t listen and violence followed.

Americans weren’t the only ones to intrigue in the borderlands. International agents worked to destabilize the region and the United States. Don Diego de Gardoqui was a Spanish agent who created disorder along the American border. Although he began his career in the United States far differently—as the Spanish minister to the United States during the American Revolution he was a diplomatic hero—he became an international scoundrel after the war. His plan: to subvert the young American Republic by persuading Americans to join the Spanish cause. Also operating in the borderlands, William Augustus Bowles, a loyalist during the Revolution, sought to create a Muskogee state in northern Florida. It would be a protectorate of Great Britain where Natives and Europeans could live together. Bowles’s actions caught the attention of both the Spanish and American governments, who did not want to see a semi-independent Native state that allowed the British back into Florida after they were expelled during the American Revolutionary War.

Treachery, speculation, malfeasance, self-dealing, foreign intrigue—all these actions attracted the label of scoundrel. At the same time, the epithet was also applied by enemies for simply having the wrong background, representing the wrong people, or challenging a revered figure. Charles Lee and Matthew Lyon were deemed scoundrels by opponents, in no small part because they had the audacity to disagree. Lyon arrived in the United States as an indentured servant and became a Republican Congressman representing Vermont. Boisterous and annoying, he attracted the ire of Federalists, who saw him as an unruly immigrant scoundrel and complained he spoke too freely and too often out of turn. To Republicans, Lyon was a working-class hero and a faithful representative of his people. Although Lyon was arrested for sedition in 1798, he still won his re-election bid from a jail cell.

General Charles Lee had the misfortune to think he was just as good a general as the hallowed George Washington. And for good reason—he had been a commissioned officer in the British Army, trained in Europe, and was experienced in warfare. Yet whatever professional expertise lay behind Lee’s opinion of Washington, he had the terrible judgment to make it public to the Continental Congress, a lapse of the political skills needed to preserve a reputation in the crucible of army command.

Much like today, scoundrels in the late eighteenth and early nineteenth centuries came in a variety of shapes and sizes, from traitors and corrupt politicians to spies, speculators, and outright criminals. However, during the Revolutionary era, opportunities for both happiness and mischief abounded as the young nation was in flux in its government, laws, and business ethics. Each chapter in this book highlights a self-interested and opportunistic man or group of men who helped shape the United States of America. Many of these men have been left out of the larger historical narrative because they have been overshadowed by other, more revered figures. Even more well-known men such as Benedict Arnold, Aaron Burr, and James Wilkinson have become secondary characters in the national story. A Republic of Scoundrels reconsiders the Founding generation and shows that they were not the monolithic group that many people revere today, but a diverse collection of self-interested and sometimes unscrupulous individuals.

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Excerpted from A Republic of Scoundrels: The Schemers, Intriguers, and Adventurers Who Created a New American Nation, edited by David Head and Timothy Hemmis. Published by Pegasus Books, December 2023.

Featured image: “The Surrender of General Burgoyne,” John Trumball