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“I really feel I do not know what’s going on in the world now,” Chuck Klosterman confessed a few days after the 2024 presidential election on the popular Bill Simmons Podcast. Klosterman, a writer and cultural critic, explained after the presidential election that it seemed to him the more information anyone has about anything, the less they are able to understand what is happening in the world. He related that he had recently conducted an informal poll among his friends about their political knowledge. “On a scale of one to ten,” he said, “how surprised were you about this election?” Among his circle, those who voraciously engaged with news media were far more caught off guard than those who casually paid attention. Klosterman was exasperated, not just by the outcome of the election, but by how he didn’t understand the world anymore. “I don’t know what to do about it,” he concluded.

There is a word for what Klosterman and millions of people in the US and throughout the world are going through: bewilderment.

Bewilderment is a feeling of inextricable confusion and a distrust of what can be grasped. It happens when the guides and signposts, the anchors that people rely on to orient themselves in the world, are suddenly pulled up and discarded. Chaos agents thrive in such an atmosphere. Klosterman has been only one of many commentators who intimated that this is an utterly new feeling; that we are entering uncharted territory, that we’ve never felt this unmoored before in the United States.

We have.

It is important that we recognize the role—and the power—that this feeling has had in American history. Bewilderment as a state of mind has occurred many times before in US history, most often when the nation was on the cusp of sudden change. The crisis of the union at the end of the 1850s immediately spring to mind, as do the crises of the Great Depression and Second World War.

Bewilderment can also be a strategy; as much as it is a state of mind, it is also a state of play. Circumstances in which people are feeling extreme disorientation are potent breeding grounds for people who are willing to exploit it to take advantage in moments of crisis. They are chaos agents who, by design, seek to use the confusion to advance their agendas, especially in the political arena where privileges and rewards can be controlled, focused, and distributed unevenly. The past teaches us that we should be on the lookout for people who greet moments of extreme disorientation with sparkling eyes, for such moments can provide certain people with extraordinary power.

Perhaps the most pertinent example happened exactly 250 years ago.

As we approach a major anniversary of American independence, we should strive to remember just how bewildering a moment that actually was for millions of people in North America. Most certainly, the confession “I have no idea what’s going on” was exclaimed, in just the same exasperated tone as Klosterman, all over the American colonies on the eve of the American Revolution.

Two hundred and fifty years ago, the wide-ranging boycott of all British goods known as the Continental Association went into effect. Passed by the First Continental Congress, this stinging measure was a significant escalation of the crisis within the British Empire. It shook people throughout North America, especially those who were skeptical of the patriot movement. Those people would soon be called loyalists, and they were completely bewildered about how the world that they thought they understood was changing right in front of their eyes. They were caught completely off guard by a political movement they wrongly thought was much smaller, less organized, and, while dangerous in its language, posed little actual threat to law and order in the British Empire.

Three hundred miles to the west of Philadelphia, in what is today Pittsburgh, feeling bewildered was almost a universal and everyday emotion on the early American frontier. If you lived anywhere near the Ohio River in the middle decades of the eighteenth century, you had watched as empires, trading schemes, and colonies came and went. The French had tried to control the region in the 1750s, then the British came and built an impressive fortress, Fort Pitt, at the source of the Ohio River. Impressive but expensive. In 1773, the cash-strapped British government decided to abandon it and let the colonists fight amongst themselves over who would control Pittsburgh.

And so they did. Virginia and Pennsylvania both claimed the region was theirs. In 1771, Pennsylvania made it part of Westmoreland County. Two years later, Virginia said, no, that same ground was West Augusta County. By the spring of 1774, there were two rival governments in Pittsburgh, each with their own leaders duking it out for control. Rivals from each colony tried to have their opponents arrested. Gangs marauded through the village looking for—and attacking—their enemies. Shots were fired. A Virginia partisan named George Aston stabbed the wife of Aeneas MacKay, a Pennsylvania official, and then two months later came back and swung a rifle butt at her head.

The man who ordered the assaults on MacKay and his wife was Dr. John Connolly. A man with a suspicious past—he claimed to be a physician but had very little medical training and he fabricated prestigious family relations—Connolly nevertheless impressed important people in Virginia society, especially George Washington and the royal governor, Lord Dunmore. Both of those men were proficient at trying to make the most out of confusion and they saw in Connolly a kindred spirit.

Connolly had recently moved to Pittsburgh, after his sister married the best tavernkeeper in town, and he used that connection to invite himself to dinner whenever anyone important appeared, George Washington among them. By the early 1770s, Connolly was becoming a big man in a very small village; the controversy that swirled about who would have sovereignty over Pittsburgh afforded him a host of new opportunities to raise his political profile and line his pockets. Dunmore met the wily doctor when he went west to visit the Pittsburgh region in 1772, and he quickly realized this was a perfect agent to advance Virginia’s agenda. When he finished his western tour and arrived back in the Virginia capital of Williamsburg, Dunmore set about pressing Virginia’s claims, first to Pittsburgh and then to points further west. The dramatic expansion of Virginia, he thought, would raise his political profile—and line his pockets, too. Dunmore appointed Connolly “captain-commandant” of Pittsburgh. Connolly was so excited, he wrote Washington to apologize that he couldn’t stop to visit Mount Vernon, because he had to go west to make war on Pennsylvania.

The civil unrest that Connolly prosecuted in the spring of 1774 was loud and attracted attention. Native peoples in the Ohio region watched in alarm as Pittsburgh collapsed into chaos. They knew that all this bewilderment would soon involve them, which it did. A vicious massacre of eight Native peoples a few weeks into the Virginia-Pennsylvania conflict turned everyone’s attention away from Connolly’s machinations in Pittsburgh. Everyone braced themselves for a war with the Shawnee, Delaware, and Mingo peoples along the Ohio River. Dunmore decided to go on the offensive and not wait for a Native strike and ordered militias to get ready to march west. The climactic battle of what would be called Dunmore’s War happened along the Ohio River at what is today Point Pleasant, West Virginia, on October 10, 1774, just as the First Continental Congress finished up the details of their boycott in Philadelphia. That battle was a big one—1,100 Virginians faced nearly 800 Natives—and it was long and nasty. When it was over, seventy-five Virginians were dead and one officer had a lung protruding from a hideous hole in his chest. “We had a very hard day,” said another Virginia officer.

The battle at Point Pleasant, 250 years ago, shows how it is essential that we recognize how bewilderment can shape history. The confusion at Pittsburgh transformed into something else, something much more recognizable and familiar to colonists who were having a difficult time understanding what was going on.

They were encouraged to do so because Governor Dunmore and his man John Connolly grasped the power of bewilderment as a state of play. They understood how confusion as a constant state of mind can offer political opportunities. Chaos agents (like Dr. John Connolly) thrive in a climate of bewilderment. To gain advantage, they sow misinformation, cast aspersions on their opponents, and rile people up even to violence. They act decisively when knowledge about something—a boundary, a dispute—is imperfect. Or they take steps to turn something that is settled, like an election, and purposely bewilder it.

Donald Trump and his political chaos agents are not the first ones to sow bewilderment and then exploit it to their advantage. There were several of them at work in Pittsburgh in the 1770s, men who were supposed to be working for governments or kings but who were really only out for themselves. They were all trying to use confusion to improve their futures and fortunes and conquer the Ohio country. We barely remember their names, but what they did there would have consequences for a quarter millennium of American history.

The American Revolution offers a lavish buffet of examples of bewilderment, both as a state of mind and a state of play. A year after the battle at Point Pleasant, George Washington had taken command of a “Continental Army” outside Boston. Colonists all over North America marched and shouldered arms to fight against King George, its own baffling experience. Governor Dunmore was drawing up plans to cut the rebellion in two, and he enlisted his man John Connolly to pull his scheme off. The two plotted for Connolly to ride again to Pittsburgh and encourage the Native peoples he had recently fought to seek revenge on the Virginians. Connolly was to lead a Native invasion of northern Virginia while Dunmore would emancipate the enslaved people in Virginia and lead them on a military campaign against the rebellious colonies. Where should these two fearsome forces link up? Mount Vernon, they decided.

When John Connolly’s servant ran away to find Washington and inform him about this devious plan (his former friends?! At his house!?!) the General and Congress issued notices all over North America authorizing the arrest of Dr. Connolly. When Patriots did find him sleeping in a tavern near Hagerstown, Maryland, he would spend the next six years locked up in a Philadelphia jail, the longest held prisoner of the Revolution. Connolly was too effective a chaos agent to be allowed his freedom. Bewilderment as a state of mind and state of play created—and then destroyed—John Connolly.

Perhaps it is a comfort that even George Washington had to have been utterly and completely bewildered about the confusing events that swirled around him in 1774 and 1775. Washington has mostly come down through posterity as a man always in complete control: the confident man on horseback, the assured President, the plantation slaveowner. But at several points in his life, he was bewildered. From his very first brushes with fame in his early twenties, Washington continually found himself swept up in events he could not control or barely even understood. In 1775, however, he was in good company. For millions of people on all sides of the Revolution—loyalists, patriots, Virginians, Pennsylvanians, Native Americans, and British officials—the sentence “I have no idea what is going on” was thought almost constantly during those years.

History is supposed to be a tonic, an antidote against feelings of confusion and helplessness in the present. When we search the past, we do so to find answers, for surety. It is the job of the historian to sort out the confusion and offer explanations. But there is something valuable in recognizing the prevalence and power of bewilderment in the past. It was as much a part of eighteenth-century lives as it has become for ours. Understanding the choices people made because they had imperfect knowledge, because they felt lost, or were just reacting to impulses can help us sympathize with them. It even helps us understand our own modern predicament, as we fumble about to make sense of new political, media, and information landscapes. Maybe it can help us figure out what to do about resolving the bewilderment that was so clearly in so many of our minds over the past days, weeks, and years, Chuck Klosterman’s included.

More importantly, however, this emphasis on “seeing” how often bewilderment occurred in American history suggests an instructive and important warning. Taking a cue from them, we need to be on our guard against those who would seek to keep us in a perpetual state of heightened anxiety and confusion. Like Dr. John Connolly, they usually have ulterior motives. But perhaps, also like Connolly, we can hope that chaos agents will be exposed and destroyed by their own machinations.

Further reading:

My inspiration for interpreting encounter on the frontier as a bewildering experience is mostly influenced by James H. Merrell’s work, especially Into the American Woods: Negotiators on the Pennsylvania Frontier (Norton, 1999) and his essay “Shamokin, ‘the very seat of the Prince of darkness’: Unsettling the Early American Frontier,” in Contact Points: American Frontiers from the Mohawk Valley to the Mississippi, 1750-1830, Andrew R.L. Cayton and Fredrika J. Teute, eds. (UNC Press, 1998). For more on the descent into violence in the Ohio Valley on the eve of the American Revolution, see Patrick Griffin, American Leviathan: Empire, Nation, and Revolutionary Frontier (Hill & Wang, 2007), and Rob Harper, Unsettling the West: Violence and State Building in the Ohio Valley (UPenn Press, 2018). For more on Dunmore, Connolly, and Virginia’s crisis in 1774-75, see the forthcoming book by Andrew Lawler, A Perfect Frenzy: A Royal Governor, His Black Allies, and the Crisis that Spurred the American Revolution (Atlantic Monthly Press, 2025).

This article originally appeared in February 2025. 

Robert Parkinson is professor of history at Binghamton University and most recently the author of Heart of American Darkness: Bewilderment and Horror on the Early Frontier (Norton, 2024). He is currently the Kundrun Fellow at the International Center for Jefferson Studies at Monticello, writing a book on the grievances of the Declaration of Independence

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