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Within two weeks of the Tampa Bay exodus, Jesup's thinking was moving even further away from stated U.S. policy. In this fascinating letter to Secretary of War Poinsett, which invokes the Jamaican maroon wars of the nineteenth century, Jesup comes close to an open challenge of the country's two main goals in the war: removing the Indians and "returning" the Seminole Negroes to slavery. The general is careful not to challenge the policies too directly, merely throwing hints, in his words, "for the consideration of my official superiors":

"We may harass them, and ultimately destroy them, but it will cost as much time and treasure as the war carried on by the British government against the Maroons. I have no books to refer to, but that war, if I remember right, was terminated by the bloodhounds; and resulted not in unconditional submission but in a treaty which secured both liberty and property to the conquered. How far such a policy would be proper in the present case I am hardly prepared to give an opinion. The question is surrounded by difficulties, view it as you will. The two races, the negro and the Indian, are rapidly approximating; they are identified in interests and feelings; and I have ascertained that, at the battle of Wahoo, a negro, the property of a Florida planter, was one of the most distinguished of the leaders; and I have learned that the depredations committed on the plantations east of the St. Johns were perpetrated by the plantation Negroes, headed by an Indian negro, John Caesar, since killed, and aided by some six or seven vagabond Indians, who had no character among their people as warriors.
   Should the Indians remain in this Territory, the negroes among them will form a rallying point for runaway negroes from the adjacent states; and should they remove, the fastnesses of the country would be immediately occupied by negroes. I am very sure they could be confined to a small district near Florida Point, and would accept peace and the small district referred to as the condition for the surrender of all runaway negroes. I throw out these hints for the consideration of my official superiors, without pretending to offer an opinion as to the propriety of adopting them; and

      I am, sir, most respectfully, your obedient servant,
            THOMAS S. JESUP