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In November 1775, a lowly veteran of frontier warfare against the Shawnee was drinking in a tavern outside Hagerstown, Maryland, when he looked up and recognized someone: His former commanding officer.
He did what he thought duty and respect commanded: He saluted.
With that simple act, a Tory plot to raise a Native American uprising and seize modern-day Pittsburgh came unraveled.
The salute drew attention and before long, local authorities realized that the man being saluted was the subject of a Colonial version of a modern-day BOL or BOLO warning — “be on the lookout.” He soon found himself under arrest.
The tale of John Connolly, the Tory plotter, is one that came to an end in Maryland but was very much a Virginia story. He was operating under the authority of Virginia’s royal governor, Lord Dunmore, who has been chased out of the Colonial capital of Williamsburg but was still actively plotting to restore royal power. Connolly’s activities were also well-known to another Virginian — General George Washington, who from his winter camp near Boston had already heard about the plan, a sign of how thoroughly Washington kept tabs on military matters throughout the Colonies.
Connolly’s story also sheds light on another little-known aspect of Virginia history: Its attempt to claim part of western Pennsylvania for its own.
That’s where we’ll begin, because all these story lines are tangled together.
Virginia claimed the future Pittsburgh and used it as a base to pursue settlement along the Ohio River
Virginia’s initial claim of territory went all the way to the Pacific Ocean, although those were later revised to just go to the Mississippi River. Either way, Virginia’s concept of itself in those days included what today is southwestern Pennsylvania. However, the French got there first. The British settlers on the coast were mostly interested in farming. The French were more focused on fur-trapping and ranged further inland. Pushing down from modern-day Canada, they established multiple outposts through modern-day western Pennsylvania in the 1750s. This alarmed Virginians; Governor Robert Dinwiddie sent a prominent militia leader to tell the French to butt out. His name was George Washington. The French shared wine and hospitality with Washington but did not butt out. Dinwiddie sent another mission, under William Trent, to build a fort near the confluence of the Alleghany and Monongahela rivers — Fort Prince George. It was half-built when the French showed up in April 1754, evicted the 40 Virginians working on it, then tore it down. In its place, they built Fort Duquesne. With that, the French and Indian War was on, the North American part of a wider conflict known as the Seven Years’ War.
The outcome was a British victory and the belief among Virginians that since they had bled for this territory, it belonged to them. Their claim, though, ran counter to those of Pennsylvanians who were also pushing west over the mountains and felt the region — now centered by what was named Fort Pitt — was rightly theirs. For a while, those conflicting claims didn’t matter much — anything west of the mountains was a long way away.
Lord Dunmore changed that. Before he became a pariah who was chased out of Virginia, he was a popular governor because he championed Virginia’s western claims. One of those claims was the land around Fort Pitt. This is where John Connolly enters the story. He was a doctor from Fort Pitt, but also a land speculator with a flair for political intrigue. At some point he showed up in Williamsburg, wheedled an audience with the governor and told him of “the extreme richness of the lands which lay on both sides of the Ohio.” This might well have been true, but it was also exactly what Virginia’s leaders wanted to hear; they specialized in tobacco but tobacco wore out the soil, so their own economy forced them to seek out more land. In any case, Connolly made a good impression. Patrick Henry remembered him as a “chatty, sensible” man.
In 1772, Governor Dunmore awarded Connolly a grant of 4,000 acres along the “falls of the Ohio” — modern-day Louisville, Kentucky — in what was then Fincastle County, Virginia. The following year, in 1773, Lord Dunmore visited the future Pittsburgh as part of his western inspection tour and made Connolly a captain of the Virginia militia. Since Fort Pitt was considered (by Virginia anyway) to be part of Augusta County, Connolly was part of a very far-flung Augusta militia.
Connolly’s plans, though, faced pressure from two sides. To the west, Native Americans took umbrage at the arrival of new settlers who were floating down the Ohio River. To the east, Pennsylvania wanted to exert control over Fort Pitt. Tensions started to rise with both groups.
When Connolly learned that Pennsylvania authorities intended to convene a court in Fort Pitt in what they intended to call Westmoreland County, Connolly flew into a rage and declared: “Damn me, if I will not oppose it!” He proceeded to take Virginia’s claims to the region to new level. On January 1, 1774, Captain Connolly called out the Augusta County militia with orders to meet at Fort Pitt on Jan. 25 for the purpose of organizing a new Virginia county to be called Pittsburgh County.
That was too much for Pennsylvania authorities. On Jan. 24, a day before Connolly intended to convene a Pittsburgh County court, they arrested him. Connolly promised the sheriff that if he were released, he would return. The sheriff unwisely let him go. Connolly kept his word, just not in a way the Pennsylvania sheriff expected. Connolly gathered up 20 armed men and rode off to the county seat of Staunton. In Staunton, Connolly talked himself into being named a Justice of the Peace for Fort Pitt and secured blank commissions to hand out to whomever he chose. Armed with these, as well as apparently an approving letter from Governor Dunmore, Connolly returned to Fort Pitt with 180 men and promptly arrested the Pennsylvania sheriff who had arrested him. When the Pennsylvania court attempted to meet, as scheduled, Connolly’s militia shut it down. Over the next few days, Connolly and his men proceeded to arrest other Pennsylvania officials.
That led to a confrontation between the Virginia and Pennsylvania governors. Dunmore conceded that Pennsylvania may have once held claim to the region, but had forfeited that claim when it “allowed” the French to occupy the area. The Pennsylvania governor, seeking peace, said he could give up part of the territory but not all. That wasn’t good enough for Dunmore, who wanted everything. “Your proposals, amounting in reality to nothing, could not possibly be complied with,” he wrote. The Pennsylvania governor, John Penn, pleaded with Dunmore to restrain his militia captain: “I would fain hope that you would not encourage Mr. Connolly in such exorbitances and outrages as are laid to his charge.”
Dunmore did not restrain Connolly. Connolly renamed Fort Pitt as Fort Dunmore and, from his base there, started sending military expeditions down the Ohio River, some of which shot at the indigenous people they came across. The natives responded in kind. Or maybe it was the other way around. In any case, there were shots fired up and down the Ohio.
Governor Penn was alarmed. He called the Pennsylvania Assembly into session and wrote to a British official: “I have also written to Lord Dunmore complaining of Connolly’s outrageous and tyrannical behavior at Pittsburgh, and representing the dangerous tendency his military operations may have to involve the colonies in a general Indian War.” Some residents of the Fort Pitt area didn’t like Connolly’s government. They petitioned the Pennsylvania governor to send militia to help liberate them from Connolly’s tyranny. “He was pulling down the houses, imprisoning and generally maltreating all those who would not acquiesce in his method of government,” according to an account by the American Antiquarian Society. The article says Connolly’s rule was notable for its “mob violence” and “too free distribution of whiskey.” Fueled by violence and alcohol, Virginia’s claim to Fort Pitt was prevailing.
Meanwhile, the violence between settlers and the Native Americans along the Ohio escalated further. The Quaker-influenced Pennsylvanians and the land-hungry Virginians had two very different ideas about how to deal with the native tribes. The Pennsylvanians wanted peace. The Virginians wanted land and, if that meant war, so be it. Lord Dunmore called out the Virginia militia and went to war. His base for that conflict: Fort Dunmore.
What quickly became known was Lord Dunmore’s War was a success — from the Virginians’ point of view. The brief war in 1774 — which made Andrew Lewis of Roanoke County famous for his victory at Point Pleasant — pushed the Shawnee and other tribes west of the Ohio. All that is prelude to what followed.
When revolution came, Connelly sided with his benefactor, Dunmore, and the crown
After the war, Dunmore ordered the county court of Augusta to convene at Fort Dunmore, not its county seat of Staunton — another sign of his interest in cementing Virginia’s hold on the area. When that court convened in February 1775, one of its first acts was the order the arrest of rival officials in the region who considered themselves Pennsylvanians.
This was all a minor backcountry drama compared to what was playing out elsewhere. The simmering conflict between the Colonists and the British over taxes and a long list of other complaints crossed a new line. The spring of 1775 saw battles in Massachusetts at Lexington and Concord. When that news reached the frontier, the people of Pittsburgh were outraged. They held two separate assemblies — one by those who considered themselves Virginians, another by those considered themselves Pennsylvanians. The latter were no longer quite so peace-loving. Their resolution declared it was “the indispensable duty of every American” to oppose British tyranny “with our lives and fortunes.” The Virginians passed a similar resolution.
Connolly, alarmed, wrote to Lord Dunmore for instructions — and eventually learned that Dunmore had been forced to flee Williamsburg for the safety of a British ship.
It was time for Connolly to choose sides. He sided with his benefactor Dunmore and the British. Connolly made plans to flee Fort Dunmore (which some by now were also calling Pittsburgh). Two nights before he was scheduled to depart, Pennsylvania authorities arrested him and sent him on his way to Philadelphia. Some of Connolly’s supporters seized the three Pennsylvania authorities who had ordered Connolly arrested and sent them to Fort Fincastle (Wheeling), where they were essentially held as hostages until Connolly was released, which he soon was. Connolly returned to Pittsburgh where “a great number of his sympathizers who were armed and impatiently awaiting his coming.” Connolly decided he’d better get some in-person advice from the royal governor, so he made his way to Winchester and then on the Virginia coast, where Dunmore was holed up in modern-day Portsmouth with the British fleet. For 14 days, Connolly conferred with Dunmore.
They apparently hatched a plan that went against much of what Connolly had stood for. Where once he fought the Native Americans, Connolly now proposed to win them over to the British side — and help the British regain the Pittsburgh area. The royal governor and Connolly devised a plan that called for the British garrison in Detroit to give Connolly some troops. With those, he would march on Fort Dunmore and nearby Fort Fincastle (modern-day Wheeling) to either seize them or destroy them if they resisted. Along the way he would distribute gifts to the Native Americans and “urge them to act with vigor in the execution of his order.” If successful, what had once been the French and Indian War against Americans would become the British and Indian War.
Their plan perfected, Dunmore dispatched Connolly on a British ship to Boston to confer with General Thomas Gage, who was busy staring down George Washington. Gage’s approval would be needed to get those British troops from Detroit. Gage liked the plan and gave orders for it to proceed. He arranged from a captain at a British garrison further west to meet Connolly in Detroit. Connolly would the lead the expedition to Pittsburgh. Once that had been secured, they would march on Cumberland, Maryland, then follow the Potomac to Alexandria, Virginia — a move that would split the American Colonies in two. It was a grand plan. There was just one problem: Connolly had been betrayed. He was accompanied by his longtime servant William Cowley. Cowley’s loyalties were different, though. Cowley also had some prior connection to George Washington.
A day after leaving Boston in mid-September, Connolly confided his plan to Cowley and asked his servant to join him on the military adventure. Connolly planned to sail back to Portsmouth to brief Lord Dunmore, then intended to go onto St. Augustine, then the capital of the British Colony of East Florida, which they had won as part of the settlement of the Seven Years’ War in 1763. From there, he intended to line up some Cherokee guides to escort him up through the Ohio country and onto Detroit. Along the way he planned to hand out royal commissions to friendly Native American tribes. Cowley took all this in and recorded the details in a letter he planned to send to Washington. When the ship stopped at Newport, Rhode Island, Cowley snuck off the ship and posted the letter.
“I hope you will please to pardon my taking the Liberty of laying these few Lines before your Excellency, but if I had not I should have thought it would have been doing a great Injustice to my Conscience, & I think every well meaning Man who is a real Friend to Liberty would join in my Sentiments to stop such outrageous Actions & Rebellious Works which are going to be put into Execution,” Cowley wrote.
Washington promptly alerted the Continental Congress. He alerted Maryland officials. He also alerted his cousin, Lund Washington, who was tending Mount Vernon in his absence. Lund Washington passed word onto George Mason, who informed the Virginia Committee of Safety, the Patriot group that was more or less in charge in Dunmore’s absence. Both Maryland and Virginia were now on the lookout.
That’s when Connolly made another mistake. He didn’t go on to St. Augustine as planned. He had begun to worry that would take too long. By now, it was already November. He decided he would sail up the Potomac as far as he could go and then go back to Pittsburgh by land. Dunmore also made two mistakes. First, he directed that Connolly send a letter to certain John Gibson in Maryland to be on the ready; it didn’t spell out plans but assured Gibson that Dunmore was in communication with Native Americans in Ohio to help Loyalists such as himself. Second, Dunmore persuaded John Smyth to go with Connolly. Smyth was a Maryland doctor who was “already well known there as a committed, and obnoxious Loyalist.” The pair were traveling through Frederick, Maryland, at the same time the local Patriot militia was mustering. Connolly — and maybe Smyth — were recognized but no one seemed to suspect anything. Connolly’s party continued on through Hagerstown. They stopped at a tavern for a while, then kept moving. Somewhere west of Hagerstown, they stopped at another tavern. That’s where one of Connolly’s former soldiers recognized him and saluted.
Smyth was worried now and suggested he and Connolly split up. Connolly wasn’t concerned. That private who saluted didn’t think anything was unusual, either. However, he went on to Hagerstown, where he stopped at the same place Connolly had earlier. The private mentioned he’d seen his old commander, and that word eventually made its way to the local militia colonel, whose ears perked up. That letter Dunmore had directed Connolly write to Gibson? It turns out Gibson wasn’t a Loyalist at all, as the royal governor had thought. He was a Patriot, and he’d turned over Connolly’s letter to the local militia. That militia now set out to find Connolly.
That night Connolly and Smyth were sleeping in a room at the tavern west of Hagerstown when the militia burst in. Smyth later wrote that he woke up to find about 35 men, mostly German immigrants, were “rushing suddenly into our room, with their rifles cocked and presented close to our heads while in bed, obliged us to surrender.”
Connolly and Smyth were taken before a local committee of safety. Smyth found the men “ignorant, rude, abusive, and illiberal.” They also decided this was a matter for someone higher and ordered the two prisoners taken to Frederick. It was not a pleasant journey for Connolly and Smyth, who wrote of his captors: “This party consisting solely of rude unfeeling German ruffians, fit for assassinations, murders, and death, treated us with great ignominy and insult; and without the least provocation abused us perpetually and with every opprobrious epithet language can afford.”
In Frederick, there was a lieutenant colonel of the Continental Army, freshly arrived from Boston. He could scarcely believe his good fortune. He knew all about Cowley’s letter to Washington, so this was a bigger catch than the locals knew. The local newspapers trumpeted Connolly’s arrest. He was eventually sent to Philadelphia and spent most of the war imprisoned. His idea of the British allying themselves with Native Americans and attacking from Detroit down to Pittsburgh survived; the British officer Henry Hamilton and Colonial administrator had the same idea — and he wound up getting captured, too. He’ll be the subject of a future story in our Cardinal 250 series; Hamilton was captured by Virginia forces and sent to Williamsburg, where Gov. Thomas Jefferson had some strong views about what should happen to Hamilton. Connolly might have been fortunate that he’d been sent to Philadelphia instead.
Five years later, in 1780, Connolly was released as part of a prisoner change — and went right back to plotting. He enlisted in the British Army and Lord Cornwallis put him in charge of Virginia and North Carolina Loyalists. He was with Cornwallis at Yorktown but fell ill and was granted leave. He apparently wandered into American lines and found himself in custody yet again. In all, he spent about seven years in confinement, unable to change the course of the war despite all of his ideas about how to do so.
The Virginia General Assembly pursued its claims to Pittsburgh and created a short-lived county there, Yohogania County
Even after Dunmore had been evicted, Patriot authorities in Virginia took up his claims to Pittsburgh. In 1776, the General Assembly created three new counties out of Augusta County — Monongalia, Ohio and Yohogania County. All three extended into modern-day Pennsylvania with Yohogania encompassing Pittsburgh. The Continental Congress didn’t think much of Virginia and Pennsylvania squabbling over this territory; that was considered a distraction from the main business of defeating the British. In 1779, the Continental Congress passed a resolution urging the two states to reach a settlement. In the end, Virginia gave up its claim to Pittsburgh and Yohogania County came to an end, although Virginia got to keep the Wheeling area (at least until West Virginia cleaved off during the Civil War).
When Connolly was finally released in 1782, the world had changed. Pittsburgh belonged to Pennsylvania and his lands at the Falls of the Ohio had been seized by Virginia. Connolly, unhappy about both outcomes, sailed to London to ask for compensation for his losses. It’s unclear whether he received any, but he returned to North America. Operating out of Detroit, he traveled through the future Ohio and Kentucky, trying to foment rebellion. Has convinced that the people of Kentucky, in particular, were ready to secede from the United States and form their own country. They were not. He angled for a position with the British government in Canada, but the British seemed tired of him. A British official there reviewed Connolly’s application and sent word to others that “for the good of the King’s service” it was important that the position in question “should at least possess those essential requisites which it cannot be presumed Lieutenant-Colonel Connolly does, and I am sorry to say as I think it my duty to be under the necessity of declaiming he does not.” In plainer language, he was passed over by the British he so desperately wanted to serve. Connolly never got any office but was given a small pension. He settled in Montreal and died there in 1813, where it was said that “the distress of his illness was considerably augmented by the effects of his disappointments that had long preyed upon his mind.”
Connolly’s role in history is that of a colorful footnote, but he had hoped it would be so much more. He considered himself a Virginian and a Loyalist to the crown. In the end, his home wound up in Pennsylvania and he wound up in exile.
Sources consulted: The American Antiquarian Society, the Annals of Augusta County, The Journal of the American Revolution, the National Archives, “The Life Adventures of Lt. Col. John Connelly, a The Story of a Tory” by Percy B. Caley, West Virginia Encyclopedia.