Three months after the first shots of the American Revolutionary War were fired at Lexington on 19 April 1775, Christopher Vail left his home on Long Island to join the Continental Army. Aged 17, he spent the next three years in almost continual military service with a range of continental, state, and militia units. Vail served in regiments raised in both New York and Connecticut, and never left those states. However, in the summer of 1778, he chose to enlist on a thirty-gun privateer. While Vail did not share the reasoning behind this decision, he was probably enticed by the pecuniary reward. Nor was service at sea likely to be an unknown quantity, since before the war Vail's father had operated a merchant vessel. Six months into the voyage the privateer was intercepted by a British schooner in the Caribbean, and Vail found himself imprisoned in Antigua. After a period of confinement, he resolved to cut short his stay by enlisting on a merchantman sailing for Britain. Over the next three years Vail served across the Atlantic with a variety of British and American privateering vessels. Vail was routinely ‘examined’ by his new employers, and questioned on his regional and political background. Upon joining a British privateer, one of Vail's comrades explained that he was not a rebel because he was not only ‘willing to fight the French and Spaniards’ but also ‘willing to fight the Americans’. Throughout his narrative, Vail identified himself variously as an American, a Yankee, and a New Yorker as his service took him to Lisbon, Cadiz, Bordeaux, Salem, and New York. Like many British Americans, Vail was unable to separate the war from the question of his identity.

The American Revolutionary War divided friends, families, and communities, and ultimately tore apart the British Empire. The imperial crisis had weakened political loyalties, but most British Americans still considered themselves to be proud Britons and faithful subjects of the king. When the political dispute became violent, it was not clear how British Americans would respond, or whether a majority would even support the conflict.