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Allen recognized a major opportunity here, but it required a critical choice. His writings attacking the tyranny of New York’s royal governor had always made a point of expressing nothing but devotion to the king. Moreover, Vermont, positioned like a dagger from Canada wedging through New England before piercing the upper reaches of the Hudson River, could be of inestimable value to the Crown. Should Vermont make good on Allen’s professions of fealty, it would undoubtedly gain control over the conflicting deeds to its land—if the British won the war. On the other hand, by denying the British this weapon and instead joining forces with the colonists, Vermont stood to gain independence as a state in an independent nation—provided the colonists won.

Being, if nothing else, an independent man—tumultuous, riotous, licentious, in the words of New York’s legislature6—Allen opted for the colonists. At first the Continental Army wasn’t sure what to do with this audacious man and his Green Mountain Boys when they ran into each other, both heading for the stronghold guarding the main highway to Canada: Fort Ticonderoga. Confusion over protocol, however, was quickly resolved, and their combined forces ousted the British on May 10, 1775—less than a month after the battle at Lexington and Concord. By surprising the British through such quick action, the Americans gained control of a vital artery.

Allen quickly seized the political opportunity afforded by this victory. He wrote to the Continental Congress, asking that the Green Mountain Boys be incorporated as a regiment in the Continental Army. The members of the Continental Congress were well aware of the group’s vigilante reputation, but under the circumstances, how could they say no? In June they passed a resolution stating “that it be recommended to the Convention of New York, that they, consulting with General Schuyler, employ in the army to be raised for the defense of America, those called Green Mountain Boys, under such officers as the said Green Mountains Boys shall choose.” Representatives from Vermont’s towns soon met to elect the commander of their now respectable and official regiment. The choice of either Allen or Seth Warren was a foregone conclusion. By a vote of 41–5 they elected Warner. Evidently, Allen’s independent nature, while ideal for rebellion, was not ideal for friendship.

To his credit, Allen continued to serve, accepting an offer from General Schuyler to perform assignments as needed. Schuyler availed himself of Allen’s persuasive skills by sending him to seek support from the French Canadians of Quebec. Allen wrote to Schuyler that he was returning with both recruits and information he’d been given regarding local pathways and routes. While returning, however, Allen’s independent nature surfaced again. He and a fellow officer, Major John Brown, concluded that the British in nearby Montreal, being focused on Schuyler’s advance, could be ousted by a surprise attack in which Allen and Brown divided their small force and slipped into opposite ends of the city under cover of night. Not wanting to lose precious time by awaiting approval, they went ahead with their plan. Allen’s men made it across the St. Lawrence River; Brown’s did not. In short order, Allen and his men were surrounded.

Allen’s defeat was no small thing. The Continental Congress had been sending letters and emissaries to the French Canadians, hoping that the province of Quebec would become the fourteenth colony to join the rebellion. Allen’s debacle, Warner wrote, “put the French [Canadian] people into great consternation.… The Canadians were before nine-tenths for the Bostonians; they are now returned to their duty.”7

For Allen, the consequence was that he spent the bulk of the American Revolution as a prisoner of war. From a public relations point of view, it was the best thing that could have happened to him. After being released in a prisoner exchange in 1778, he was widely hailed—in no small part because