Jackson acknowledges that he received a letter from Knox on 22 August 1790. Laments that it was not within his power to take care of a debt that Knox asked him to settle in Worcester. Says he heard from a vessel from the West Indies that on 15 July war had been declared on England, but Jackson does not believe it, though he wishes in god it may be true. Reports that Benjamin Austin, Jr. and Thomas Dawes, Jr. are candidates for Federal Representatives for this district in the Room of Mr. Ames. Expects opposition, but believes we shall be able to counteract them. Says that John Gardner writes under the name of Yankee criticizing the Society of Cincinnati. Free stamped on address leaf with no signature.

General Jackson did not receive Knox's letter of 30 August 1790 because he had been out of town. Jackson had met with two men named Jonathan Dow and Ebenezer Eastman interested in purchasing a Township from Knox. The land is between Northern Stream and Lower debscot. These men assure Jackson they can bring in forty families to settle it immediately. Jackson needs to know what Knox wants to do about the situation. Jackson calls Knox's attention to an extract of a letter (in the newspaper) by Spanish Ambassador Don Diego de Gardoqui which points an end to the prospects of War. Jackson also informs Knox that John Gardner's attack on the Cincin [Society of Cincinnati] is in the Chronicle, adding to the twenty items attacking the Society he has already written. Jackson thinks that the number of Candidates for Federal Representatives in the several districts might have a positive impact but that is yet to be determined. Fisher Ames has Jackson and Knox's support, and Benjamin Austin, Jr. and Thomas Dawes, Jr. are also running.

Discusses an upcoming meeting with the Society of the Cincinnati. Says the standing Committee would like to know if the Constitution of the Society will be voted on during the next meeting. Asks the number of delegates Knox believes will be necessary to handle the business at the meeting. Believes it more convenient if Knox were to handle the whole business himself. Mentions it has been reported that Gov. [Arthur] St. Clair and Major [Winthrop] Sargent have been taken by Indians.

Writes that it gives everyone pleasure to hear Mrs. Knox is well a Bed - I please myself the Child will do well altho appearances may at present be against it. Discusses the brief arrival in town of a Major [possibly Richard] Platt and mentions his financial problems. Will visit Isaac Winslow to consult him on the business Knox mentions. Discusses local business and political issues, such as the opening of the General Court and the speech by the Governor to both houses. Heard reports that 7,00 men were armed in Springfield to oppose sitting of the Supreme Court and that even more men are in arms to support the government. (Refers to Shays' Rebellion) Does not know how this will end but hopes something important will come of it. Refers to an upcoming meeting of the Society of the Cincinnati, and a great honor earned by General [John] Sullivan. Also refers to meeting the Minister of the Netherlands, who is in town. Sends his love to Lucy Knox and the children.

Thanks Knox for his letter of condolence on account of his father's death. Discusses Secretary of State Alexander Hamilton's plan for the federal government to assume state debts. Writes, [t]he nonassumption of the State Debt has thrown the people into the greatest confusion, and will be the means of weakening the Federal government more than any other measure they could have persued... Believes that unless this measure is obtained in the present session of Congress, very serious consequences will take place... Mentions a number of public creditors had a meeting on Thursday, and will meet again on Tuesday, to hear a report from the Committee. Also mentions the theft of goods from the customs house. Says the goods were found in a barn on the north side of the town and that evidence was found on a ship in harbor and linked to the captain's son; says both Ship & Goods are believed to be condemned.

Writes, The time taken up by Congress in fixing the permanent seat of Government, and the situation of the Funding business has caused a great uneasiness & clamour amongst the people, and of that Class that have been the firmest supporters of the government ... every mechanick & Tradesman conceives that their being out of employ is wholly owing to that circumstance - and the distress of that class of people in the several seaports in this State is very alarming - in this town it is melancholy to see the poverty and wretchedness of the inhabitants... Reports that Captain Vose, managing affairs on Knox's lands in present-day Maine, informed him that the people who live there are behind in their payments. They will not make any payments until the Massachusetts General Court decides on a petition related to the land. Relates, a Spanish War remains as it did...

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.