With the Non-Importation Act as a weapon, the President was confident that Monroe, who had once more returned to his post in London, could force a settlement of all outstanding differences with Great Britain. To his annoyance, and to Monroe's chagrin, however, he was obliged to send a special envoy to act with Monroe. Factious opposition in the Senate forced the President to placate the Federalists by appointing William Pinkney of Maryland. The American commissioners were instructed to insist upon three concessions in the treaty which they were to negotiate: restoration of trade with enemies' colonies, indemnity for captures made since the Essex decision, and express repudiation of the right of impressment. In return for these concessions, they might hold out the possible repeal of the Non-Importation Act! Only confirmed optimists could believe that the mistress of the seas, flushed with the victory of Trafalgar, would consent to yield these points for so slight a compensation. The mission was, indeed, doomed from the outset, and nothing more need be said of it than that in the end, to secure any treaty at all, Monroe and Pinkney broke their instructions and set aside the three ultimata. What they obtained in return seemed so insignificant and doubtful, and what they paid for even these slender compensations seemed so exorbitant, that the President would not even submit the treaty to the Senate. The first application of the theory of peaceable coercion thus ended in humiliating failure. Jefferson thought it best "to let the negotiation take a friendly nap"; but Madison, who felt that his political future depended on a diplomatic triumph over England, drafted new instructions for the two commissioners, hoping that the treaty might yet be put into acceptable form. It was while these new instructions were crossing the ocean that the Chesapeake struck her colors.
James Monroe is one of the most unlucky diplomats in American history. From those early days when he had received the fraternal embraces of the Jacobins in Paris and had been recalled by President Washington, to the ill-fated Spanish mission, circumstances seem to have conspired against him. The honor of negotiating the purchase of Louisiana should have been his alone, but he arrived just a day too late and was obliged to divide the glory with Livingston. On this mission to England he was not permitted to conduct negotiations alone but was associated with William Pinkney, a Federalist. No wonder he suspected Madison, or at least Madison's friends, of wishing to discredit him. And now another impossible task was laid upon him. He was instructed to demand not only disavowal and reparation for the attack on the Chesapeake and the restoration of the American seamen, but also as "an indispensable part of the satisfaction" "an entire abolition of impressments." If the Secretary of State had deliberately contrived to deliver Monroe into the hands of George Canning, he could not have been more successful, for Monroe had already protested against the Chesapeake outrage as an act of aggression which should be promptly disavowed without reference to the larger question of impressment. He was now obliged to eat his own words and inject into the discussion, as Canning put it, the irrelevant matters which they had agreed to separate from the present controversy. Canning was quick to see his opportunity. Mr. Monroe must be aware, said he, that on several recent occasions His Majesty had firmly declined to waive "the ancient and prescriptive usages of Great Britain, founded on the soundest principles of natural law," simply because they might come in contact with the interests or the feelings of the American people. If Mr. Monroe's instructions left him powerless to adjust this regrettable incident of the Leopard and the Chesapeake, without raising the other question of the right of search and impressment, then His Majesty could only send a special envoy to the United States to terminate the controversy in a manner satisfactory to both countries. "But," added Canning with sarcasm which was not lost on Monroe, "in order to avoid the inconvenience which has arisen from the mixed nature of your instructions, that minister will not be empowered to entertain... any proposition respecting the search of merchant vessels."