Writes to inform Jackson that his father, Henry Knox, has died. Relates that Knox swallowed a chicken bone and could not recover. Stresses how miserable his family is because of the death.

Writes that his father passed away the day before, stating that he was calm & resigned, and died in full faith of perfect happiness in the world of spirits - this was a great consolation to my honored mother & to his Children & friends around him - my aged mother is very much afflicted, and cannot reconcile the separation they having live'd together fifty eight years last month, and but very little apart during that period - Goes on to discuss matters regarding the raising of troops and a possible appointment in the military, though he states but why do I mention QMG [Quarter Master General] - I am not anxious to be a soldier at my time of life... Also discusses the will of his late father and how the estate is to be divided.

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.

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.

Informs Knox that he has picked up a visitor, (Mr. William Bingham), and discusses the events of the day. Notes he will provide Bingham with the information he has per Knox's instructions. Free stamped on address leaf with no signature.

Writes that he is very upset at the sudden death of his brother, Joseph, which happened the previous Friday. Is traveling to Brookline to see his brother's widow and daughter. Touches on financial arrangements with Knox and with Mr. [James] Swan.