This paper examines the strategic leadership competencies of British General William Howe during the American Revolution (1775-1778). During the American War of Independence, General Howe displayed periodic tactical brilliance and operational competence but consistent strategic ineptitude. After arriving in America, Howe was quickly thrust into the position of Commander-in-Chief of British Forces and General of North America. Howe's lack of self-awareness, ineptness in managing the personalities of his subordinate commanders, personal biases, and lack of political savvy resulted in the strategic failure of the British war effort. Howe's difficulty in transitioning from tactical, through operational to the strategic level provides a useful example as to the dramatically different challenges faced by current leaders as they prepare for and address similar challenges in our contemporary operational and strategic environment.