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Jesup's constrained anguish at making a battlefield recommendation of policy was evident in the tone of his first letter, sent to Secretary of War Poinsett on February 11, 1838:

"As a soldier it is my duty, I am aware, not to comment upon the policy of the government, but to carry it out in accordance with my instructions. I have endeavored faithfully to do so; but the prospect of terminating the war, in any reasonable time is anything but flattering. My decided opinion is, that unless immediate emigration be abandoned, the war will continue for years to come, and at constantly accumulating expense. Is it not well worthy the serious consideration of an enlightened government, whether, even if the wilderness we are traversing could be inhabited by the white man (which is not the fact,) the object we are contending for would be worth the cost? I certainly do not think it would; indeed, I do not consider the country south of the Chickasa-Hatchee worth the medicines we shall expend in driving the Indians from it.

"If I were permitted -- and it is with great diffidence that I venture to make the suggestion -- I would allow them to remain, and would assign them the country west of the Kissimmee, Okee-Chobee, and Panai-Okee, and east of Pease Creek, south, to the extreme of Florida. That would satisfy them....

".... I respectfully commend the measure to your consideration, and that of the President, as the only means of terminating, immediately, a most disastrous war."