Charles Winstone’s letter book offers a rich first-hand account of Caribbean history during the American Revolution, the French invasion, and the occupation of Dominica.The American Revolution and French presence disrupted the island's economic life. As Dominica's former solicitor and attorney general, Winstone became a central figure to absentee planters and British firms protecting estates and investments. His letters reveal efforts to forge new trading networks through the Dutch West Indies as he worked for British absentees based elsewhere in the Caribbean and Europe. The correspondence also reflects his struggle to establish a West Indian fortune on the backs of enslaved people cultivating coffee and sugar. His letters provide a rare look at the world of a plantation attorney and manager as he oversaw several estates near the colonial capital of Roseau during the most tumultuous years in Dominica’s history and reflects on the ineffective and unprepared British response upon the outbreak of the American conflict, particularly noting French military preparations on the nearby islands of Martinique and Guadeloupe.