Received Knox's letter of 2 May 1791. Thanks Knox for his promise respecting the appointment of Marshall. Jackson believes that another, unrelated Mr. Jackson will try to hold on to that appointment along with the other appointment he holds. Says, I have no fears in this head as the President will not approbate so great an impropriety as one man holding two Offices under the government. Goes on to discuss the issue of government appointments and the problem with choosing some men and leaving others out. Explains that were the Deputies appointed by the President, they would have some claim upon his patronage, but in the present case they have none. Knox is the only person that Jackson trusts with his request. Jackson would like to visit Knox but his mother would be greatly distressed.

Reports that Cousin Isaac (likely Isaac Winslow) has departed for Georges River (possibly St. George River in Maine, near the Waldo patent lands). Writes, General [Benjamin] Lincoln appointment as one of the Commissioners to Treat with the Southern Indians has given great Satisfaction to the people in this quarter, particularly to his friends who are exceedingly gratified in the confidence placed in him by the President. Continues to emphasize his interest in the position of Collector of the Port of Boston, but also discusses the position of Marshall and the duties and salary associated with it. Discusses the recent anonymous publication of a poem which is universally despised by all parties & descriptions of men, and provides his suspicions on who the author may be. Mentions his positive response to the bill for the War Department.

Discusses his disappointment with apparently not receiving a government position, but knows that Knox did everything in his power to help. Would prefer, if possible, to be appointed in the Revenue department. Comments on the appointment of General [Benjamin] Lincoln and of Mr. Lovell. Mentions the severely hot weather they have recently experienced in Boston, and sends his love to Mrs. Knox and the rest of the family.

Discusses recent correspondence between himself and Knox, recently appointed Secretary at War. Discusses business and financial matters pertaining to Knox (apparently, Jackson was managing Knox's affairs while Knox was in New York).

Mentions the illness of Lucy Knox, related to the recent passing of one of the Knox children. Discusses the recent bill describing the salaries of the various executive departments. Mentions General [Benjamin] Lincoln's recent appointment and his leading troops to negotiate with the Creek Indians in Georgia. Comments on his own prospects for receiving an appointment in the Revenue office or as Marshall. Also mentions the arrival of a French ship in the Boston area, as well as a bill from Captain [Thomas] Vose, Knox's agent in the Waldo patent.

Jackson received Secretary of War Knox's letter of 10 April 1791. Comments on various military appointments and the recruits from Massachusetts. He says, the Officers in this Town have inlisted five or six but they are not such men as you want for the service. Mentions that gentlemen in the area are pleased that Knox has sent people to survey the area for the canal. Writes that Mr. Jonathan Jackson will try to hold both his appointments, that of Marshal, and in the Excise. Jackson does not approve. Gives his opinion to Knox about other candidates.

Has received the news that Knox's son has died. Sends his condolences to Knox and his wife and discusses the difficulty of losing a child. Has enclosed a letter for the President from Mr. Thomas Edwards, the former Judge Advocate, who is very poor at present and would like an appointment in the judicial branch as a clerk. Would like to pursue for himself the office of Marshal, and explains why he is well-suited for its duties. Also discusses his suitability for several other positions, but leaves it to Knox, who is in the seat of government, to represent his interests there.