1. David Holmes’s 20 June 1810 letter to Robert Smith (DNA: RG 59, TP, Mississippi) discussed the political situation in West Florida. Holmes reported that Spanish authority in the province had virtually collapsed, to the point that the resulting “sense of common danger [had] induced some of the inhabitants to establish a kind of neighbourhood police” whose operations were both “inefficient” and “unjust.” The “mixed nature” of the population had, moreover, led to the development of parties favoring American, British, and Spanish interests, and, until recently, there had also been a French party. The “American party” wished to see the province become part of the U.S., but Holmes believed its members hesitated to act from fear of the consequences of failure. He also stated, though, that they would rather take the risk than be subjected to any other power or the “perils of anarchy.” The British party wished for the protection of Great Britain, while many of the French party had recently removed to Orleans Territory after having been ordered to leave the country. Holmes further noted that “a great portion of the population of West Florida consist[ed] of slaves, and persons without character, or the means of procuring a comfortable living.” These facts led him to ask what would be the effect of a “state of Anarchy and confusion” upon the adjacent territories of the U.S., and he predicted that should the “respectable” and “well disposed” portions of the community be overcome in any struggle, “we shall be placed in a very unpleasant if not in a precarious situation as respects our slaves.” Holmes concluded by observing that Great Britain was the only foreign power likely to interfere in West Florida, and he assumed that the U.S. must be “considered in some degree interested” in the outcome.

2. In his 10 July 1810 letter to Robert Smith, Robert Lowry, agent-designate to the revolutionary junta at Caracas, reported that he would be ready to leave by the end of the month (DNA: RG 59, CD, La Guaira; printed in William R. Manning, ed., Diplomatic Correspondence of the United States concerning the Independence of the Latin-American Nations [3 vols.; New York, 1925], 2:1144). Lowry also related conversations he had in Baltimore with two agents from Caracas, Juan Vicente Bolívar and Telésforo d’Orea. The former told Lowry that he had placed orders for muskets to be sent to Caracas, while the latter mentioned a meeting he had attended the previous week in Philadelphia with Francis James Jackson, Luis de Onís, Juan Bautisa Bernabeu, and the recently displaced Spanish governor from Caracas. The Spanish officials believed that Great Britain would probably not favor their cause to the extent that they had hoped, especially if the revolutionaries in Caracas should repudiate totally the authority of Ferdinand VII.

3. Robert Smith to Robert Lowry, 12 July 1810, acknowledged receipt of Lowry’s letter of 10 July and informed him that papers for his mission would be ready by 20 July (copy, DLC) (1 p.; in John Graham’s hand; docketed by JM).

4. See Robert Smith to David Holmes, 21 July 1810 (letterbook copy, DNA: RG 59, DL), where Smith instructed Holmes to have the territorial militia of Mississippi ready for service in the event of “foreign interference” or “internal convulsions” in West Florida. Smith also sent to Holmes a copy of portions of William C. C. Claiborne’s 14 June letter to William Wykoff, Jr., authorizing Wykoff to go to Baton Rouge to assure the West Florida settlers of “the friendly disposition of the American Government” and to encourage them to form a convention to determine the future of the region. Claiborne’s letter, Smith declared, had been “written under a sanction from the president.” Smith further enclosed “some instructions issued from this department, marked A,” which were subsequently identified by Clarence E. Carter as a letter written to Wykoff by the secretary of state on 20 June. These informed Holmes of the selection of an agent for the “confidential purpose of proceeding without delay into East Florida, and also into West Florida, as far as pensacola for the purpose of diffusing the inpression that the United States cherish the sincerest good will towards the people of the Floridas as neighbours … and that in the event of a political separation from the parent Country, their incorporation into our Union would coincide with the sentiments and the policy of the United States” (see copy of Smith to Holmes, 21 July 1810, and enclosures [DNA: RG 59, TP, Orleans]; enclosure “A” reprinted as Smith to Wykoff, 20 June 1810, in Carter, Territorial Papers, Orleans, 9:883–84).

The obvious differences, if not total incompatibility, between these two sets of instructions, supposedly written to Wykoff within the space of one week, require some explanation. Assuming that Smith was not trying to confuse Holmes about the nature of Wykoff’s mission, it is plausible to suggest that his 20 June letter was not, as Carter claimed, to Wykoff but was, instead, the enclosure in his letter of the same day to William Harris Crawford requesting the senator to select “a gentleman of honor & discretion qualified to execute a trust of … interest & delicacy” (ibid., 9:885). Neither the RC of Smith’s letter to Crawford nor its enclosed “letter of instruction” has been located, but it would seem that State Department clerks, in fulfilling JM’s request to inform Holmes of the administration’s policy toward West Florida, sent the Mississippi governor a copy of the latter along with the extracts from Claiborne’s 14 June letter to Wykoff.