Hedging His Bets: Ethan Allen, the Haldimand Negotiations, and Allegiance in the American Revolution

Benjamin Anderson

It was the summer of 1780 when Ethan Allen, Vermont’s self-proclaimed leader, was approached by a man on a dusty road to Arlington. Beverly Robinson, a Virginian Loyalist and friend of British Commander-in-Chief Henry Clinton, looked down at Allen from atop his horse and handed him a piece of paper. It was a proposal to Allen and Vermont: renounce their commitment to the Union, return to the British Empire, and they could potentially be rewarded with a “separate government under the king and constitution of England” with their lands validated.[1] Allen promised to consider the proposal and Robinson rode into the distance.

This episode and what was to follow demonstrated Allen was not unlike the average American during the American Revolutionary War. By promising to consider Robinson’s proposal, he was hedging his bets, looking to side with whoever he thought was likely to win the war. In recent decades, historians, especially of the southern theater of war and New York, have discovered that this action was not unusual during the Revolutionary War. Survival trumped patriotism.[2] In Vermont, as Allen exemplifies, land validation transcended nations and ideals.

The struggle for land validation was the overwhelming issue in Vermont (called the New Hampshire Grants prior to its declaration of independence in 1777) stemming from the confusion and uncertainty that characterized the eighteenth-century colonial borders. From the 1740s to the start of the Revolutionary War, both New Hampshire and New York staked claims to it and issued land grants that amounted to millions of acres. To facilitate a personal profit, the avaricious and opportunistic New Hampshire Royal Governor Benning Wentworth sold land grants at incredibly cheap rates, thus attracting many New Englanders to the region. On multiple occasions, they clashed with the New York authorities, who demanded they pay quitrents to validate their lands.

Statue of Ethan Allen by Larkin Goldsmith Mead, via Wikimedia Commons. No contemporary image of Allen is known to be extant.

Allen arrived in the Grants after a decade of misery and personal failure. Ever the opportunist, he declared himself the settlers’ new leader and immediately set about uniting the population around a collective identity and against New York. He coordinated the resistance to New York with the Green Mountain Boys and terrorized the Yorker authorities and settlers. Informed by the same Lockean arguments of liberty and property as the colonists that protested Britain’s enforcement of various taxation measures, Allen’s leadership was just as much influenced by his commitment to securing his family’s future through land speculation. In 1773 he created the Onion River Land Company with his brother and cousin. By the start of the Revolutionary War, they had accumulated a land empire, namely in the western Grants, that amounted to some 70,000 acres worth more than $100,000. Such figures would ensure Allen’s immediate and wider family would be sustained for many generations to come.

Initially, Allen hoped King George III would validate these lands and, therefore, protect the New Hampshire Grants settlers from New York, but when the Revolutionary War erupted, he perceived Britain to be just as tyrannical as New York, and, subsequently, a threat to his land empire and the New Hampshire Grants settlers’ liberties and land. He saw the United States of America as best placed to protect his interests because it also fought for his beliefs in liberty and property. “I read with a sort of philosophical horror,” he wrote, “the first systematical and bloody attempt at Lexington, to enslave America, [which] thoroughly electrified my mind, and fully determined me to take part with my country.”[3] He pushed hard for the Grant’s entry to the Union when he returned to the newly independent Republic of Vermont from British captivity in 1778, but the Continental Congress’s approval was not forthcoming.

Far from accepting the new state, it appeared to be just as much a threat to Allen’s land empire as the tyrannical New York or British by encouraging Massachusetts and New Hampshire to stake their claims to the land, thus preparing for its decimation. Further, it appeared willing to sacrifice the region to the British Army. It was “torn by intrigues of the enemies of Congress,” his youngest sibling recalled. Already impatient with Congress’s intransigence, its delegates then humiliated him when they refused him entry in 1778 because it did not “recognise [him] as [a] representative of an independent state.”[4] With Britain looming menacingly in the north and Congress planning to decimate Vermont from the south, it seemed the state was surrounded by enemies on all sides. Once more Allen’s allegiance slowly shifted: this time to the Republic of Vermont and its inhabitants. Nevertheless, his allegiance to himself and his family’s survival transcended this loyalty to the Vermonters.

With interest, Britain watched Vermont’s relationship with Congress decline. After General John Burgoyne’s defeat in 1777 and then France’s entry into the war in 1778, George III and the British government decided to bribe the enemy, leading to that fateful meeting between Allen and Robinson in 1780. After receiving Robinson’s letter, he and his associates agreed not to pursue the matter any further, but on 29 October 1780 Allen met with Justus Sherwood, a former Green Mountain Boy turned Loyalist spy, at Castleton, where a truce and a prisoner exchange was agreed. Yet, they also entered a private conference for several hours because Sherwood had another offer for Allen: Vermont could claim “those privileges they have so long contested for with New York” if they returned to the Empire.[5]

Hoping against hope, Allen insisted he wanted no involvement in any “damned Arnold plan to sell his country” because he was “sincerely attached to the liberties of America.”[6] Nevertheless, he would not reject the offer because he recognised Congress’s intransigence over Vermont’s entry into the Union and “it seemed materially to concern the whole people of Vermont whose liberties and properties for a number of years past were much dearer to him than his own life.”[7] He would not accept the offer unless Congress acted in the same tyrannical manner as Britain, and further, he could not commit to it because he feared a backlash from Vermonters. His solution was to use propaganda to inform them about Congress’s tyrannical ways whilst maintaining Vermont’s status as “a neutral power free and independent of any other power on earth.”[8] He hoped Congress would eventually accept Vermont, but if the United States decided to attack it, he would seek Britain’s assistance.

Eventually, Allen’s brother Ira Allen and his friend Joseph Fay replaced him in the negotiations. He retreated into the background to take up a new role in the negotiations that was designed to protect Vermont from the dangers presented by Britain and the Continental Congress. Using a negotiating tactic that he learned from Native Americans, he created confusion between the U. S., Vermont, and Britain. He handed Robinson’s letter over to Congress, promising nothing would come of it and secured a truce on the New York frontier; yet he also created Greater Vermont by annexing land in New Hampshire and New York, turning the small republic into a miniature empire, thus making itself more attractive to Britain.

Frederick Haldimand, circa 1778, by Joshua Reynolds. National Portrait Gallery, via Wikimedia Commons

Truces between Vermont and Britain were continually extended throughout 1780 and 1781, but Sherwood’s and Haldimand’s patience was reaching its limits. “To us,” Sherwood observed, “it appears they wish to have two strings in their bows, that they may choose the strongest.”[9] They were not totally wrong. The leading figures in Vermont’s government, who were either friends or related to Ethan, signed two letters that demonstrated they were hedging their bets on the Revolutionary War’s outcome: one, addressed to Congress, insisted the negotiations were not genuine and another, addressed to Britain, insisted Vermont was serious about returning to the Empire. Despite the reservations, Haldimand remained committed to welcoming Vermont back into the British Empire.

In October 1781, he proposed a plan to Ira Allen. British troops would move along Lake Champlain and offer Vermont a proclamation that would seal their return to the British Empire as an independent colony. With 200 men, Lieutenant Colonel Barry St. Leger and Sherwood sailed up Lake Champlain to Ticonderoga, but then the plan went to pot. After looking for a Vermonter to deliver Haldimand’s proclamation, Sherwood accidentally killed a Sergeant Tupper and took six Vermonters prison. The British fed them and then released them with a letter of apology from St. Leger to Vermont’s Governor Thomas Chittenden. This letter fell into the hands of Ethan’s domestic opponents, who took it to the Assembly and demanded answers from Ira Allen and Chittenden. They suspected treachery afoot but could find no compelling evidence. Days later, the British were defeated at Yorktown and the curtain started to fall on the Revolutionary War, and as the curtain fell so did any chance of Vermont returning to the British Empire.

Yet that was not the end of the matter for Ethan Allen. Throughout the 1780s, he maintained contact with the British and continued to push for Vermont rejoining the British Empire. He was “as rapacious as a wolf,” according to Haldimand.[10] As late as 1788, he made overtures about a potential alliance or Vermont rejoining the empire as a means of protecting Vermont from a threatening United States, as well as its invaluable trade that was dependent on Quebec and the St. Lawrence River.[11] Nothing, however, came of it, and less than a year later he died on his way home from South Hero Island.

Benjamin Anderson is a PhD student at the University of Edinburgh, where he is studying the Loyalists of Vermont during the American Revolution. You can find him on Twitter at @Ben_Anderson44 and on LinkedIn.


[1] Vermont Historical Society [Henceforth VHS], Collections of the Vermont Historical Society, 2 vols. (Montpelier: VHS, 1870-1871), II, 60.

[2] Christopher F. Minty, “ ‘Of One Hart and One Mind’: Local Institutions and Allegiance During the American Revolution,” Early American Studies: An Interdisciplinary Journal, 15 (2017), 99-132; Sung Bok Kim, “The Limits of Politicization in the American Revolution: The Experience of Westchester County, New York,” Journal of American History, 80 (1993), 868-889; Albert H. Tillson Jr., “The Localist Roots of Backcountry Loyalism: An Examination of Popular Political Culture in Virginia’s New River Valley,” Journal of Southern History, 54 (1988), 387-404; Joseph S. Tiedemann and Eugene R. Fingerhut, “Introduction” in The Other Loyalists: Ordinary People, Royalism, and the Revolution in the Middle Colonies, 1763-1787 (Albany: State University of New York Press, 2009), 1-18.

[3] Ethan Allen, A Narrative of Col. Ethan Allen’s Captivity (Burlington: Chauncey Goodrich, 1846 edition), 11.

[4] Nathaniel Peabody to Josiah Bartlett, 13 July 1779 quoted in Paul Hubert Smith (ed.), Letters of Delegates to Congress, 1774-1789, 26 vols. (Washington: Library of Congress, 1976-2000), XIII, 213

[5] Justus Sherwood cited in John Pell, Ethan Allen (Boston: Houghton Mifflin, 1929), 200-203.

[6] Ibid.

[7] Ibid.

[8] Ibid.

[9] VHS, Collections, II, 149.

[10] Frederick Haldimand quoted in Charles Jellison, Ethan Allen: Frontier Rebel (Syracuse: Syracuse University Press, 1969), 295.

[11] Ethan Allen to Guy Carleton, 16 July 1788 in John J. Duffy et al (eds.), Ethan Allen and His Kin Correspondence, 1772-1819, 2 vols. (Hanover: University Press of New England, 1998), I, 273-275


Featured image: Capture of Fort Ticonderoga, Henry Bryan Hall and James Smillie, New York Public Library, via Wikimedia Commons.

Latest Comments

  1. Tamara Langford says:

    To Borealia and Benjamin Anderson. Enjoyed your article and it added to my own research regarding a Loyalist ancestor.

  2. nalmat59 says:

    To Borealia and Benjamin Anderson … Thank you for this article. I enjoyed it as it did tie in with my own reading and research of a Loyalist ancestor.

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