Assuming the position of Lieutenant Governor after service as a brigade major in the French and Indian War, Hamilton took command of Fort Detroit along with other British claims in the Northwest American frontier. For such a large amount of land, Hamilton was only given approximately 300 soldiers to police the frontier. To keep American settlers out of this British-claimed territory Hamilton looked beyond his meager number of British soldiers. He looked to the local Native American tribes north of the Ohio River. Arming them, Hamilton sent them on raids into Kentucky and other coveted land. Many Kentucky settlers were so distraught because of these attacks that they regarded 1777 as the “year of the bloody sevens.”
These Kentucky raids were not uncharacteristic of the frontier. Raids were a familiar sight on the frontier during the Revolution while the large decisive battles were fought in the east. To fight back against British-allied Native Americans, Lieutenant Colonel George Rogers Clark of the Virginia militia ordered attacks on British outposts including Vincennes, Kaskaskia, and Canokia. Successful, Rogers captured the outposts. Hamilton, however, did not accept defeat and launched a counterattack victoriously retaking Vincennes and the nearby Fort Sackville in December of 1778. This British victory was short-lived as George Rogers Clark struck back in February of 1779. Rogers’ American forces were too much for Hamilton. Succumbing to defeat, on February 25th Hamilton did not raise the British flag over Fort Sackville.
After the American capture of Vincennes and Fort Sacville, Hamilton was sent as a prisoner to Williamsburg, Virginia. After his exchange, he became Lieutenant Governor and eventual Deputy Governor of Quebec. Exchanging the cold of Canada for sunshine, Hamilton later served as Governor of Bermuda and Antigua.