Early in 1776, while in the midst of overseeing his army's siege of British-held Boston, General George Washington received at his headquarters in Cambridge, Massachusetts, an anonymous letter from a citizen on the fringes of the British colonial empire.

“Sir,” the letter began. “You may reasonably imagine that it is presumptuous in me to take such liberty in writing to your Excellency; still, its going from one whose principles are actuated from the genuine feelings of liberty, and an indelible anxiety for the happiness of his country.”

The writer went on to express solidarity with America’s “great struggle” against the crown; and strongly hinted that rebellion could be fomented in his neck of the woods—with support from the general. “We would greatly rejoice could we be able to join with the other Colonies, but we must have other assistance before we can act publicly.”

Scholars today believe that the unsigned letter was likely written by John Allan, an influential merchant and politician in Nova Scotia—today, one of Canada’s Maritime Provinces, but then a crown colony.

For 200 years, historians have been debating the question of why Nova Scotia never became the 14th colony to join the American Revolution. It had close ties with the rebellious colonies, after all: An estimated three-quarters of Nova Scotia’s population of 20,000 at the time of the Revolution were New Englanders.

To Americans today, the idea that there were 13 colonies—and 13 only—seems sacrosanct. It certainly didn’t look that way in 1776. Nobody then saw the northern territories as something separate; certainly not a separate entity called Canada.

“There is no Canada at this point,” explains historian Margaret Conrad, professor emeritus at the University of New Brunswick. “There is British North America.”

Actually, there once was a part of France’s North American colonies called Canada. But when the British took the land as part of the spoils of the French and Indian War of the 1750s and 60s, they renamed it Quebec. That, too, was a colony at the start of the American Revolution—as were far-off Newfoundland and tiny Saint John’s Island (today known as Prince Edward’s Island). But of the crown’s four northern colonies, none had such close ties to those in rebellion as Nova Scotia.

In the years after the war, the British government expelled French Acadian inhabitants and, eager to re-populate the land with English-speaking colonists, offered their land for cheap to nearby New Englanders. The colonial capital of Halifax was a military garrison town founded in 1749 as a counterweight to the then-French fortress of Louisbourg a few hundred miles up the coast.

The city and the province attracted the interest and presence of some now-familiar names on both sides of the impending Revolution. Benjamin Franklin owned land in Nova Scotia. General Charles Cornwallis, who would later surrender to Washington at Yorktown, was the nephew of Nova Scotia’s Royal Governor. Horatio Gates, the American hero of Saratoga (and nemesis of Washington) was stationed there as a young British officer.

As things heated up in Massachusetts in the early 1770s, Nova Scotians responded in kind. Echoing their independence-minded cousins to the south, the same Committees of Correspondence and Safety that united the 13 colonies began popping up in Nova Scotia. There were also acts of civil insurrection: A large consignment of hay, bound for Boston where it would be used as forage for the British army occupying the city, was burned in Halifax before it could be loaded onto transport ships. A Canadian Hay Party, if you will.

In 1775, Washington sent two spies to Nova Scotia to assess whether the colony was indeed ripe for rebellion. The agents proved remarkably inept, claiming that they weren’t even able to find a ship to get them across the Bay of Fundy into the colony. More encouraging was a meeting in February 1776 with representatives of the native peoples of Nova Scotia, who expressed solidarity with the American cause.

And yet the revolutionary spirit in Nova Scotia was stamped out early. One reason? Simple bad luck.

In March 1776, a delegation of Nova Scotians eager to lead a rebellion in their colony arrived at Washington’s headquarters in Cambridge just as the British were evacuating Boston. As recounted by historian Ernest Clarke in his book The Siege of Fort Cumberland 1776, the delegation—Jonathan Eddy, Isaiah Boudreau and Samuel Rogers—met several times with the general in a building at Harvard College. But Washington was pre-occupied with where the British fleet, still anchored in Boston Harbor, would head next.

“Timing is everything, and this was bad timing on part of the Nova Scotian emissaries,” says historian Barnet Schecter, author of George Washington's America: A Biography Through His Maps.

Although he dutifully passed the emissaries along to Congress, Washington declined to aid his visitors’ cause. While applauding what he called the “spirit and zeal” of the liberty-loving people of Nova Scotia, he expressed concern that the invasion of a colony not already in rebellion would make Americans the aggressors. “I apprehend such an enterprise to be inconsistent with the principles on which the Colonies have proceeded,” he wrote.

It was a specious argument. The Americans had already invaded a colony that was not in rebellion—Quebec. And it hadn’t gone well. Indeed at the very moment of the Nova Scotian delegation's arrival in Cambridge, Benedict Arnold's starving and smallpox-ridden army was languishing just outside Quebec City, having been defeated in their attempt to take it the previous December.

Arnold was Washington's best general and despite his valiant efforts, the attempted invasion of Canada had been a disaster. "Washington was probably thinking 'If Arnold and his army couldn't do it, what chance do these guys have?'" Schecter says.

“Maybe Washington thought they didn’t have much chance of success,” Schecter says.

If so, he was right. The bad timing continued for the Nova Scotians when they arrived in Philadelphia—just as Congress was busy debating the Declaration of Independence. Rebuffed again, the rebels did go on to launch a series of small and largely unsuccessful military actions back home; a campaign still known in Canada as “Eddy’s Rebellion.”

Allan, the man who is believed to have written the anonymous letter to Washington, made a little more progress. He too traveled to Philadelphia and, perhaps arriving at a more opportune time than his colleagues, met with Congress in early 1777. According to Clarke, he convinced the representives to back an expedition into Nova Scotia, the first step of which would involve Allan returning home to organize the native tribes against the British. Allan, now a colonel in the Massachusetts militia, did broker friendly relations with the Indians, and some historians credit his efforts for protecting otherwise defenseless American settlements in what is now eastern Maine from attack. But the invasion of his home colony that he had dreamed of never materialized.

Recent scholarship suggests colonists hesitated to rise up for several reasons: influential clergymen who opposed the rebellion; long distances between settlements that stymied efforts by rebels to act in concert; the intimidating presence of the large British military base in Halifax.

Still, perhaps the biggest reason that Nova Scotians didn’t join the Americans may have been the Americans themselves. At the time, American privateers operating out of New England ports were ravaging Nova Scotia’s coast. “The privateers come early on in the conflict,” says Conrad. While they couldn’t stand up to the British fleet, “they could do a lot of damage in hit-and-run raids.”

They didn’t discriminate against loyalists, neutrals or those inclined to support the patriot cause, either. Nor did Congress, Washington or anyone else seem able to control them. “Numerous settlements received nocturnal visits from the heartless New Englanders,” wrote historian John Dewar Faibisy. “They entered harbors, rivers and coves, committing various depredations on land, burning vessels in port and at sea seizing valuable prizes.”

The behavior of these raiders, Conrad says, “took away a lot of the sympathy for the rebellion.” As one Nova Scotian wrote at the time: “Robbing poor innocent ones has bin a grate means to Coule [cool] the Affection of many well wishers to the Just proceedings of America.”

When the main theater of war moved to the middle and southern colonies, Nova Scotia braced itself for a new American invasion. This time, it was loyalists fleeing the United States, a country where they could no longer live in safety. After the war, in 1784, the mainland of Nova Scotia was carved into a new entity, New Brunswick, for these American refugees.

When Canada became a nation in 1867, both Nova Scotia and New Brunswick were among the original four provinces. But as the country expanded west in the 20th century, the importance of Atlantic Canada diminished and its economy deteriorated—leaving behind an intriguing series of “What if?” questions. What if people like Eddy or Allan had succeeded in their missions? What if Congress had been able to restrain the overzealous privateers? Could Nova Scotia have become the 14th colony to join what would become the United States?

“I doubt the British would have let Nova Scotia go easily,” says historian Jeffers Lennox of Wesleyan University in Connecticut.

Hopes of a 14th colony may have been misplaced, but commercial and social intercourse between Nova Scotia and New England endured. “There’s a long history of migration back and forth that continues after the war,” says Lennox. “And there remains a real facility and familiarity between these two regions.”

Indeed, the bonds that even the American Revolution couldn’t completely sever are still evident today. Just ask a Halifax football fan what his or her favorite team is. The inevitable answer?

The New England Patriots.