Expresses disappointment that Knox will not be in Boston but states that to clear the way for you I have settled with nearly all Mr. F.s creditors - most likely referring to some money owed. Discusses land business. Gives his love to David.

Informs Knox the legislature will rise before the 19th and Knox needs to come to Boston, Massachusetts immediately. Notes how important the situation is for Knox and his family.

Long narrative about how Knox's son, Henry Jackson Knox, has been misbehaving in Boston and spending money excessively, particularly on clothes. Reports during one Henry's weekends with him that Henry evaded and deceived me (Jackson) in every instance... his act and address, - the improper company he kept both male & female, seldom coming home until 11 or 12 O Clock - pockets full of money, and showing me in every instance, gave me great distress & uneasiness... Reports after this incident he had a very pointed conversation with Henry and told he needed to return to Hingham the next day. After procuring two horses and stableman to escort Henry, while busy in his room with business, Jackson was informed that Henry had sent the horses back but was planning on riding in a carriage back to Hingham. Jackson later saw Henry still in town in a sleigh with one of our Players. Upon seeing Jackson, Henry sent the player home but evaded Jackson. Says Henry hired a hack and took two common girls with him and went to a house out of town, where I have since learnt he frequently visited... Says the next day he procured a man and a sleigh and sent Henry back to Hingham. Has instructed the Preceptor not to allow Henry to visit Boston again during his next vacation nor does Jackson ever wish to see Henry in Boston again. Writes that since Henry's returned to Hingham Jackson has been informed of Henry's conduct more than I had an Idea of - Cards - Wine & Women were his continual pursuit, - at Taverns & bad houses were his constant places of resort - Mentions several gentlemen who Henry had tried borrowing money from but was refused.

Jackson acknowledges receipt of Knox's letter of 24 October 1790 and was pleased to learn that Knox had arrived safely in New York. Jackson and others in Boston had received word of a coach accident that severely injured Mrs. Knox and some of their children. To the astonishment of every body, Governor Bowdoin is yet living, Jackson reports, for a week past every moment was supposed to be his last. Bowdoin is a good and valuable man, and his death will be much lamented by his family and the public at large. Jackson comments on the performance of Knox's horse, Boston, saying that Knox will not regret buying the horse. Lists items he is sending to Knox with Captain Barnard including cranberries for Mrs. Knox. Jackson remarks that he has heard nothing further respecting the Fish, and I think it will not do for me to make the first advances on that head.

Expresses disappointment at not hearing from home for some time, even though he has sent several letters himself. Notes he would have written sooner but he has been expecting a visit from Knox any day. He has decided to go ahead and write since it looks like Knox will not be visiting until May. Discusses interactions with friends and sends his love to the rest of the family. Say the people of this town are in general, good federalists, for they celebrated the day appointed by the President for a public thanksgiving... Complains of his mother (Lucy Knox) forgetting his letters to her and wishes she would show a generous mind or a thankful heart.

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.

Advises Knox to prepare his plans for the barn and stables (Montpelier). Mentions Mr. [Ebenezer] Dunton will be on hand to prepare for the work and to secure the timber. Notes the left over timber from the house might be salvaged and used on the barn. States he does not believe Captain Seavor will accept a lieutenancy. Discusses various bonds he has drafted and the recent election held in Boston, Massachusetts. Mentions the people's agitation with the advancement of the British.