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Two weekends ago, I enjoyed an afternoon at Toronto's Art Gallery of Ontario. One of the first works I saw on this visit were these two terracotta busts by one Hamilton Plantagenet MacCarthy. The one in the back is of Sir Isaac Brock, an acting Lieutenant Governor of Upper Canada who died in an early battle of the War of 1812. The one in the front is of Tecumseh, the Shawnee leader who tried to create an Indian confederacy to Upper Canada's west and fell in battle a year after Brock.

The project to which Brock devoted his life, that of an Upper Canada that was part of the British Empire, succeeded. Barring sustained British defeats on the front lines, I would argue that was a more likely outcome than not. Tecumseh's confederacy, in contrast, did not survive his death, and would arguably have been hard-pressed to survive, not least because of American pressure on territories that had been ceded to the US back in 1783.
A commenter on Facebook linked to his analysis of a scenario where the Confederacy survived. The description of British demands, found here, describes terms that would be difficult for the Americans to accept.
The Treaty of Greenville, originally signed in 1795, set generous boundaries for the confederacy.

I have serious doubts as to whether this would be viable. The weakness of the First Nations alone, particularly demographically, would be a problem. The situation of the American citizens already resident in this autonomous zone--a territory that, I believe, would still be part of the United States--would seem certain to keep everyone entangled most uncomfortably. The result could easily be a second war on the Great Lakes at some point. Tecumseh's confederacy, even if successful, might only postpone the marginalization of indigenous peoples in central North America for another generation. His initiative came too late.
Was there any way that Tecumseh's project could have survived? Perhaps we could have had Michigan become a Native American polity under Britain? Tecumseh could plausibly have survived; Britain could plausibly have done better? Or were the odds too great for any long-duration survival?

The project to which Brock devoted his life, that of an Upper Canada that was part of the British Empire, succeeded. Barring sustained British defeats on the front lines, I would argue that was a more likely outcome than not. Tecumseh's confederacy, in contrast, did not survive his death, and would arguably have been hard-pressed to survive, not least because of American pressure on territories that had been ceded to the US back in 1783.
A commenter on Facebook linked to his analysis of a scenario where the Confederacy survived. The description of British demands, found here, describes terms that would be difficult for the Americans to accept.
Within a week, Lord Castlereagh sent precise instructions which confirmed the worst fears of the Americans. The Indian boundary line was to follow the line of the Treaty of Greenville and beyond it neither nation was to acquire land. The United States was asked, in short, to set apart for the Indians in perpetuity an area which comprised the present States of Michigan, Wisconsin, and Illinois, four-fifths of Indiana, and a third of Ohio. But, remonstrated Gallatin, this area included States and Territories settled by more than a hundred thousand American citizens. What was to be done with them? 'They must look after themselves,' was the blunt answer.
In comparison with this astounding proposal, Lord Castlereagh's further suggestion of a 'rectification' of the frontier by the cession of Fort Niagara and Sackett's Harbor and by the exclusion of the Americans from the Lakes, seemed of little importance. The purpose of His Majesty's Government, the commissioners hastened to add, was not aggrandizement but the protection of the North American provinces. In view of the avowed aim of the United States to conquer Canada, the control of the Lakes must rest with Great Britain. Indeed, taking the weakness of Canada into account, His Majesty's Government might have reasonably demanded the cession of the lands adjacent to the Lakes; and should these moderate terms not be accepted, His Majesty's Government would feel itself at liberty to enlarge its demands, if the war continued to favor British arms. The American commissioners asked if these proposals relating to the control of the Lakes were also a sine qua non. 'We have given you one sine qua non already,' was the reply, 'and we should suppose one sine qua non at a time was enough.'
The Treaty of Greenville, originally signed in 1795, set generous boundaries for the confederacy.

I have serious doubts as to whether this would be viable. The weakness of the First Nations alone, particularly demographically, would be a problem. The situation of the American citizens already resident in this autonomous zone--a territory that, I believe, would still be part of the United States--would seem certain to keep everyone entangled most uncomfortably. The result could easily be a second war on the Great Lakes at some point. Tecumseh's confederacy, even if successful, might only postpone the marginalization of indigenous peoples in central North America for another generation. His initiative came too late.
Was there any way that Tecumseh's project could have survived? Perhaps we could have had Michigan become a Native American polity under Britain? Tecumseh could plausibly have survived; Britain could plausibly have done better? Or were the odds too great for any long-duration survival?