In the first letter, written 20 December, Jackson relates that he and Colonel [Benjamin] Hichborn will meet Knox in Portland, Maine on 1 January 1800. In the second letter, written 22 December, Jackson reports that he forwarded a letter from Knox to Henry Jackson Knox. Discusses financial matters related to Knox, Mr. A. Smith, and Mr. Gorham.

Informs Knox he received Knox's letter of the 20th but has not received the two letters under cover from Mr. Swan that Knox said were coming. Insists that Knox has very wrong Ideas respecting Mr. J.J.'s situation his Children are all well provided for, & he a large property in the [illegible]. - but I don't believe he will accept to be 2d. to Mr. S.

Jackson tells Knox that Knox's statement and the hundred dollar bill enclosed came safe to hand. Jackson will be at Portland with Col. Hichborn January 1, 1800. Jackson demands that Knox be punctual in meeting them and says that nothing but death could prevent them from going to Portland. In a post script Jackson notes that he has just received a letter from Knox's son, Henry Jackson Knox. Jackson tells Knox, The Secretary of Navy order'd him onboard the Constitution.

Colonel Jackson discusses military details, noting that the Court, (referring to the Court of Massachusetts) has ordered the draft of every seventh man from towns that have not met enlistment quotas. He has persuaded the court to allow drafted men to choose which regiment they will join. Notes that General George Washington has ordered him to send weekly reports of his (Jackson's) proceedings. Wants Knox to apply to George Washington to give an order on his behalf for arms and accoutrements. Asks Knox other military advice, noting, as I have never been in the Service I wish to be as regular as possible, in all my proceedings, & Shall be ambitious to enter the field with as much reputation as possible for your sake, as well as my own. GLC02437.00591 and GLC02437.09451 were originally one document.

Also includes copies of letters Jackson wrote to Captain Vose on 14 and 15 September. Contains 3 Jackson signatures. References Knox's letters of 5 and 7 September. Is happy Knox has given up the idea of building the large house this fall. Says Vose cannot determine the spot to build upon yet. Wants Knox to make a visit to help determine the house's placement. Sent Vose [Dollar sign]200 and various supplies yesterday. The copies of the letters to Vose state that Jackson will get supplies and carpenters ready for the spring. Also says I conclude you [Vose] will consent to make an addition to the Old house to accomodate General Knox's family this spring. Goes into further details about the house and claims to be in negotiations with a good man to build the house this spring. Reports that Mr. Bridge advertised Knox's land for sale to pay for taxes because Jackson's letter took 20 days to be delivered by the post office. Hopes to see Knox in Boston by 25 September.

Discusses his visits to friends and the most violent snow storm we have had since the year 1780 ... Expresses his concern on not hearing from Knox, as never since our acquaintance first took place, do I remember such an instance as the present - it is now more than a month since you wrote me ... I am my dear Harry really at a loss, indeed I cannot conjecture the reason why I am forgotten - and I assure you I shall continue very unhappy and distress'd until this matter is explained - I have writen [sic] you every Sunday since you left Boston and shall continue so to do and I pray you to do the same, and in the case we shall hear from each other by every Wednesdays mail, and altho we are one hundred miles farther distant from each other we shall receive Letters once a week as usual - Mentions information regarding interaction between Spain and England.

General Jackson is happy to have received Secretary of War Knox's letter of 28 December 1790. Mentions a card party he is attending with a small circle of female friends. Free stamped on address leaf with no signature.