Monroe's appointment as minister to France came at an opportune time. The dispatch of controversial Federalist John Jay on a mission to Britain had raised fears among the Anti-Federalists of alienating France–more or less America's only ally on the world stage. The appointment of Monroe, a solid friend of the French, was meant to appease critics of Washington's foreign policy. However, general incompetence on the part of Washington's secretary of state prevented Monroe from getting a clear picture of world affairs before leaving. He did not know that Jay had been given sweeping powers to discuss trade issues with the British and left assuming that Jay was limited to settling disputes as laid out in earlier treaties. Had Monroe been better equipped with knowledge of Jay's mission, his meetings with the French government would have been far more productive. As it was, Monroe's "misrepresentations" would hurt his reputation.

As he departed America, Monroe again faced money troubles. He had narrowly avoided bankruptcy earlier and sold off several slaves to help his brother avoid bankruptcy. Monroe had plenty of wealth, but much of it was tied up in land and so not readily available for cash. Throughout his life he suffered an almost chronic cash shortfall–a shortfall exacerbated by his seeming unwillingness to be reimbursed by the government for his expenses. As he left for France, Monroe paid off several previously unknown debts belonging to his brother, and so missed his chance to purchase five thousand acres in Loudon County.

Monroe and his family sailed for France on June 18, 1794, bringing with them two white servants to help the family. They arrived in France on July 31. He immediately discovered how the French felt towards Americans, whom they felt had betrayed their ally. Monroe's diplomatic bags were searched and the food he had brought with him was impounded. Luckily, it appeared that attitudes toward America might be changing. Robespierre and his anti-American administration had fallen days earlier; Monroe arrived only five days after Robespierre's execution. The Committee of Public Safety was busier with controlling mobs in Paris than foreign affairs, and so was ill-equipped to argue with ambassadors.

On August 13, Monroe requested a chance to address the government. He hastily wrote an address praising the French for their devotion to liberty and carefully avoided any reference to revolution. His address was met very warmly, and the French passed a resolution urging that an American flag be placed next to the French one in the assembly hall. Monroe, despite his money problems, purchased a silk flag with silver stars and gold fringe. At home, however, Monroe's speech was not as well received. Madison wrote to Monroe that the speech to the French government had angered the Federalists and been "very grating to the ears of many." This would be the biggest problem Monroe would face through the term in France: A general misunderstanding of his role as minister. He saw himself as meant to counter-balance Washington's pro-British foreign policy, and more often than not, Monroe sounded like a Anti-Federalist mouthpiece than a diplomatic minister. He constantly worked to tighten Franco-American alliances, even when that was not what he was supposed to be doing.

On September 3, Monroe presented the French government with a list of American grievances with France. Again, however, he overstepped his powers by heaping praise upon the government's trade policies. Over the next two years, almost every ship from Baltimore would carry a rebuke from Washington's secretary of state for one misstep or another. Monroe was not cut out to be a minister. One July 4th, for instance, at a dinner for Americans in Paris in honor of Independence Day, Monroe did not toast President George Washington, as was the custom. The oversight, whether intentional or not is up for debate, led to scuffles in the audience and when news trickled home of the incident, it only strengthened Monroe's detractors.

Then, in 1794, Monroe found himself battered by a treaty signed by Jay in England. When the French requested information about the treaty, Monroe assured them that it would not concern new trade obligations–again not knowing that Jay had been given power to negotiate commercial concerns. Thus, when the treaty finally was announced and it contained trade provisions, Monroe faced steep criticism from the government. The seeming thaw in Franco-American relations ended abruptly. Over the coming years, France rolled back many of the protections it had awarded U.S. merchants in retaliation for Jay's Treaty.

By 1796, enthusiasm for Monroe as the minister to France had cooled considerably. He faced growing criticism at home and in France. Secretary of State Timothy Pickering charged that Monroe ignored orders from the U.S. government. Charles Pinckney was sent to France to replace Monroe, but he found himself given the cold shoulder by the French government, who refused to seat him. Nevertheless, Monroe took leave of his post in December and in his final ceremony, he harshly criticized Washington's Farewell Address and his foreign policy. Pickering angrily commented that Monroe's address was "unpardonable." In the spring, Monroe returned home.

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