Matchekewis first appears in the historical record in 1763 in the windup to Pontiac's Rebellion, when he and other Native leaders besieged Fort Michilimackinac and took it from the British. This was a rare feat, happening only one other time during the Seven Years War, when Cherokee captured Fort Loudon in what is now Tennessee. After Pontiac's Rebellion, Matchekewis led his people to what is now Michigan, trying to keep away from Settlers, but to no avail. He later allied with the British during the American Revolution, and led a war party of over 750-1,000 warriors from combined tribes against the Spanish outpost at St. Louis, Missouri in 1780. Unfortunately, this time, faced with a tipped-off ragtag garrison of volunteers, he faced defeat.
Not to be outdone, Matchekewis was also active in the Northwest Indian War, 1785-1795, but like many other leaders, came to believe that resistance to the American would only prove futile and harmful to his people in the end. He was a signatory of the Treaty of Greenville in 1795, ceding Bois Blanc Island in Lake Huron. After the treaty parley, he disappeared from the historical record.
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