His great grandfather was Sir Frederick Hamilton, Baron Paisley and Governor of Ulster, a position which necessitated a change of residence from Scotland to Ireland for the family and resulted in Henry's birth a century later. He was commissioned into the 15th Regiment of Foot in the British Army.
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(It is not clear whether she had any children but the Colonial Society of Massachusetts newsletter number 336 of March 1902 says Governor and Mrs.
Hamilton had one child, Mary Anne Pierpoint, who died unmarried on December 12, 1871).
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His eventual parole, release to the British for a huge ransom, exchange in 1781 and repatriation to London were difficult and complex because of the American complaints.
From there, he was Lieutenant Governor of Quebec, then Governor, from 1782 to 1785.
He soon acquired a notorious reputation from American historians of the time as the "Hair Buyer of Detroit") for helping British financed Indians scalp rebel Americans on the frontiers.