Born about 1750 in Fermanagh County, Ireland, Caldwell emigrated to Pennsylvania in 1773. During the American Revolution he served with the British forces as a captain in Butler's Rangers at Niagara and Detroit. In 1784 he obtained land near the mouth of the Detroit River and became one of this area's earliest settlers. Caldwell's exceptional influence with the local Indians enabled him to obtain control of some 4450 additional hectares on the north shore of Lake Erie where he encouraged former Loyalist soldiers to settle. In 1812 he commanded the Western Rangers in actions at Miami (Ohio) and the Longwoods and, after his appointment as a Deputy-Superintendent of Indian Affairs in 1814, he led Indian forces at the battles of Chippawa, Lundy's Lane and Fort Erie.