Levi Allen, younger brother of the more renowned Ethan Allen, was a complicated man when it came to his loyalties to the crown and the movement for independence. Ethan Allen, on the other hand, was a fiercely strong supporter of actions against the crown and an advocate of independence. Ethan and Levi were prominent land speculators in Connecticut, New Hampshire and Vermont and would have been outraged by the limits to westward expansion in the Proclamation of 1763 as well the same taxes that irked the upper class across New England. Ethan in particular had many quarrels with the colonial government of New York over land speculation, and would have benefited from being able to settle these disputes with a friendlier governor and court system.
Ethan Allen was also a prominent military commander and lead a group of volunteers known as the Green Mountain Boys, who assisted Ethan in defending his land from New York speculators and surveyors. While the Green Mountain Boys were less politically motivated than other New England groups such as the Sons of Liberty, they did fall on the side of independence once the Revolutionary War broke out. It was the Green Mountain Boys that Ethan Allen lead to capture Fort Ticonderoga after the battles of Lexington and Concord. Ethan’s brothers Levi, Heman and Ira fought alongside him in the battle of Fort Ticonderoga, showing a clear favoring of independence among the Allen family.
Levi Allen would not remain loyal throughout the remainder of the war. After the capture of Ethan Allen, Levi left Vermont for New York where he began trading with British businessmen. Levi would remain more loyal to his business interests than to politics throughout the rest of the war and afterwards. Levi eventually became an outspoken loyalist due to his ties to businesses in British Quebec.