Front Page Titles (by Subject) TO JAMES MONROE. 1 - The Writings, vol. 2 (1783-1787)
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TO JAMES MONROE. 1 - James Madison, The Writings, vol. 2 (1783-1787) 
The Writings of James Madison, comprising his Public Papers and his Private Correspondence, including his numerous letters and documents now for the first time printed, ed. Gaillard Hunt (New York: G.P. Putnam’s Sons, 1900). Vol. 2.
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TO JAMES MONROE.1
Philadelphia, August 17th, 1786.
I have your favor of the 14th inst. The expedient of which you ask my opinion has received, as it deserved, all the consideration which the time and other circumstances would allow me to give. I think that, in the present state of things, such an arrangement would be beneficial, and even pleasing to those most concerned in it; and yet I doubt extremely the policy of your proposing it to Congress.2 The objections which occur to me are: 1. That if the temper and views of Congress be such as you apprehend, it is morally certain they would not enter into the accommodation. Nothing, therefore, would be gained, and you would have to combat under the disadvantage of having forsaken your first ground. 2. If Congress should adopt your expedient as a ground of negociation with Guardoqui, and the views of Spain be such as they must be apprehended to be, it is still more certain that it would be rejected on that side, especially under the flattering hopes which the spirit of concession in Congress must have raised. In this event, the patrons of the measure now before Congress would return to it with a greater eagerness and with fresh arguments, drawn from the impossibility of making better terms, and from the relaxation into which their opponents will have been betrayed. It is even possible that a foresight of this event might induce a politic concurrence in the experiment.
Your knowledge of all circumstances will make you a better judge of the solidity or fallacy of these reflections than I can be. I do not extend them because it would be superfluous, as well as because it might lead to details which could not prudently be committed to the mail without the guard of a cypher. Not foreseeing that any confidential communication on paper would happen between us during my absence from Virginia, I did not bring mine with me.
[1 ]From the Works of Madison.
[2 ]“It has occurr’d to G[rayson] & myself to propose to Congress that negotiations be carried on with Spn. upon the following principles: 1. That exports be admitted thro’ the Mississippi to some free port—perhaps N. Orleans, to pay there a toll to Spn. of abt 3 pr. centm. ad valorem & to be carried thence under the regulations of Congress. 2. That imports shall pass into the Western country thro’ the ports of the U. S. only. 3. That this sacrifice be given up to obtain in other respects a beneficial treaty. I beg of you to give me yr. opinion on it.”—Monroe to Madison, August 14, 1786, Writings of Monroe, i., 151, 152.