Knox explains to Williams the situation surround Henry Jackson Knox and his refusal to accept midshipman status after being refused promotion to lieutenant. Knox's son appears to have no proper value for money, and is therefore very extravagant. Knox thought the Navy would help straighten his son out, but now Knox fears his son will be involved in a course of errors and vices which may overwhelm him. Knox asks Williams to take him on and help Henry Jackson Knox overcome his weaknesses. Knox is afraid his son's love of gambling has left a considerable debt that Knox cannot pay. Knox prefers that his son rejoin the Navy, but if that is not possible, Knox thinks it would be best if son travel to Maine to be with his parents. Henry Jackson Knox should travel by water and not land because land travel would be more expensive and he would be too distracted by bad company and tempted to stray if went by land. If President Adams is still in Philadelphia and Williams thinks it is appropriate to consult him on this matter, Knox consents to allow Williams to do so.

Williams writes Knox about his son Henry Jackson Knox and hopes that his son intends to return to his ship. Williams comments on the changes in the administration which I think forebodes a settlement of some sort or other with France. Williams says it is assumed that Adams will lose the next election. Talks about a meeting of Federalists who want to run Pinckney and Adams equally, which Adams will see as abandonment. He wishes rather to take the chance of being second to Jeff than to P. Relates a letter James McHenry sent to him saying that he wished Williams to have a post in the Secretary of State's department. Williams accepted and began the work, only to be told by President [John] Adams that he was appointing someone else.

Encloses a letter from his brother Bradford, who is much alarmed at the appearance of a rival candidate in the person of [a] mutual friend Harry Jackson. Expresses no wish to sway Knox's opinion, but does ask for his Opinion of the requisite Qualities of the two Candidates ... conclude that [he] will ... Support the pretensions of the man [he has]... esteemed. Goes on to discuss Patrick Henry and his resignation from the Virginia government since there is every reason to believe this State will no longer oppose the assumption of their debt, but quietly acquiesce in the funding system. The great popular Leader Henry wished to raise a clamour against the Federal Government and he struck at the assumption but Seeing that he would involve himself in absurdity to continue this opposition, without providing funds to pay the Interest of the State Debt & Seeing that this would strike at the root of his popularity he has wisely retired ... Stain on the address leaf where the letter was sealed and stamped R H ION May 10. Watermarked C Taylor and with a hunting horn inside a crest with G R underneath. Free stamped on address leaf with no signature.

Offer his congratulations on an appointment to the army and discusses other business. Noted as written at Mount Pleasant, state unknown.

Williams discusses Knox's business affairs and debts. Williams explains to Knox that he would decline a military commission from President Adams, meaning no disrespect. Williams says, In serious truth I had rather have a civil than a military station, tho' were I 15 years younger and a war impending I would prefer it to all this.

Williams tells Knox that many people are disappointed that Knox has chosen not to join the army. Williams worries that Knox's absence will hurt his own career: As it is I fear my military career will be bounded by a Lieutenacy in a volunteer Corps of Cavalry. He regrets not remaining a private and says since therefore I am destined for the field in case of war I may as well enter fully into the service (if I can) immediately; I wrote for this purpose a note to Genl Hamilton. Williams goes on to talk about his prowess as an artillerist and that some say he should be considered for promotion to major. Williams says he has not asked Knox to talk to Hamilton because of the perception of impropriety. He believes Knox would do it anyway if he sees that fit. However, the truth is that without asking nothing seems likely to be obtained. In a postscript, Williams notes that Lt. Col. Edward Carrington was selected as Quarter Master General of the U.S. Army.