When the British lost their American colonial territories in 1781 at the end of the American Revolutionary War, it was the culmination of events that began as far back as the conclusion of the American Theatre of the Seven Years’ War (the French and Indian War, 1763). Examples include changing dynamics in British Parliamentary charters, the involvement of American international allies (primarily France, Spain, and the Dutch Republic) seeking retribution for the French and Indian War, shortages of supplies and munitions, misjudgements regarding Loyalist support, and independent British generals failing to coordinate their military offensives. However, one less-discussed example is the disconnect in leadership styles among the three British Commanders-in-Chief of the American Colonies from 1775 to 1783: Thomas Gage, William Howe, and Henry Clinton. This paper will assess their leadership failures as they navigated their varying styles during the American Revolutionary War (1775-1783).