The collection mainly consists of letters from James Wilkinson to his friend Samuel H. Smith, a major general in the Maryland Militia during the War of 1812, and United States senator and representative from Maryland. It is in these letters that Wilkinson is the most open, with frank comments about his foes in the territorial government, as well as about Burr, his allies, and the conspiracy trial. An example of Wilkinson's candidness can be seen in a postscript in a letter dated December 10, 1806. In it he writes, "I shall live to laugh at my vile detractors as I have done all my life -- and after being crowned Emperor of Mexico, in place of Burr, I will return to spend the eve of my life in my native state and not far from Baltimore." In another letter dated June 20, 1807, he forthrightly states that he believes the conspiracy trial will not last more than four months, as Burr will attempt to flee justice. In the same letter, Wilkinson remarks that he believes an assassination attempt will be made on his own life.
Many of the letters reference Wilkinson's ongoing political conflicts with Return J. Meiggs, a politician from Ohio and judge in the Louisiana and Michigan territories; Judge John B. C. Lucas, chief justice of the Louisiana Territory; and Samuel Hammond, a member of the armed forces and Georgia state senator. Lucas served as a congressman from 1803 until he replaced Wilkinson as civil and military governor of the upper Louisiana Territory in 1805. Wilkinson often writes of his thoughts on political and military matters, discussing tensions with England and talk of an embargo against them, which would become the Embargo Act in December, 1807. The letters also frequently refer to Aaron Burr and detail Wilkinson's involvement in the ensuing conspiracy trial from his point of view.
The first letter in the collection introduces a friend, John Coburn, to the governor of the District of Natchez, Manuel Gayoso. Wilkinson's papers contain a copy of a letter from Andrew Jackson to Claiborne. In it, Jackson warns Claiborne to guard against internal and external enemies, which refers to Wilkinson as "the General." There is also a letter from Harman Blennerhassett, a wealthy Irish immigrant who was one of Burr's co-conspirators, to a Dr. Wallace. In this letter, Blennerhassett requests the retrieval and shipment of personal effects left behind after his attempted escape and capture for his involvement in the Burr conspiracy. James Brown, who was appointed attorney for the United States in New Orleans by Thomas Jefferson, writes personally to Wilkinson. Brown's letter covers political matters and Wilkinson's professional struggles.
Envelopes do not accompany the letters and in some cases the addressee is not known. In one instance, denoted by brackets around the name, it has been assumed that the recipient of the letter is Samuel H. Smith, as at that time, he was a confidant of Wilkinson and was in frequent correspondence with him.