The first Quere your Excellency has been pleas’d to submit to the consideration of your Generals is, that admitting the Enemy to aggregate their Force at New York and to retain a naval superiority both in Harbour and at Sea, their number then ammounting to 16090 Men, whether it is probable we shall obtain men and means sufficient to undertake the siege of New York, what force will be necessary for this purpose, & what number of Militia should be demanded of the States. Tho’ the Subduction of New York under this description would be difficult, it is in my opinion far from being impossible if Men and Stores can be had. the former I should hope might upon this occasion (the object being a favorite one) be obtain’d from the States, who would I should conceive Exert themselves both to embody & support the Men demanded of them, and which in the present state of our Finances is I fear unfortunately but too requisite—To be able to furnish Convoys, to preserve our communications & to prevent our being Beaten in Detail, I conceive that nearly if not quite Triple the number of the Enemy would be necessary as many therefore as when added to our Regulars of Every Description, would make up this number should be requir’d of the States.

Not knowing the present State of our Magazines I am not competent to judge Whether the Military Stores we have are adequate to our purposes, but those we have, and what I presume we might obtain from the States and from our Allies, would probably be sufficient—I have formerly strove, and have of late particularly Exerted my self to gain information of the situation of the Enemies Works at all points, & in Which I persuade my self I have not been wholly unsuccessful; they are now so strong upon York Island, and are Every moment becoming so much more so, that I deem an approach that way too Hazzardous if not intirely impracticable, nor is this all, should we succeed by that passage New York would not be an Easy Situation (if at all tenible) While Brooklyn heights are possessed by the Enemy; That then if we attempt a Siege should in my opinion be our first object. In that case a body of Troops sufficient not only to hold the Enemy in check but to fight them should they attempt to double us by Water, or otherwise come out, should be Posted in the Vicinity of Kings Bridge, and to be still more Secure should be assisted by strong Works. I take it for granted that works upon the Banks of the North River at proper places would preserve our Water Communication from the operation of a Fleet, & should single vessels slip by to prevent our intercourse, they might be so perplex’d by cannon that they would not long continue the interruption. The Communication with long Island may I think with moral certainty be preserved by proper Fortifications at Morisinia Point, Montresors Island, and an Island next to it. Variously designated by being call’d [Buchanchan’s], Great Barn, or Eldridges Island, Your Excellency knows the Island I mean: The Communication at this place it is true may not be practicable upon a larger Scale at particular times of tide, but it is always so I am informed for small well man’d good, Rowing Boats, & is practicable in a Military sense at least four times in twenty four hours, and as we ought not (if unaided by Ships) to throw ourselves upon Long Island but in such force as to set the Attacks of the Enemy at Defiance that, I should conceive would be sufficient Communication. The Watermen Employ’d should by no means be taken by Accidental Drafts from the line, but should be a settled stationary Active Band of men, Well vers’d in the principles of the occupation they are to follow, and if possible intimately Acquainted with the navigation where they are to Operate. I am aware that the Enemy may annoy us by Batteries at some places from Harlem, but this is an inconvenience which from the nature of things Lines of Communication & of Approach are generally if not always Liable to, and as from a pretty Accurate observation of Montrezanes Island it appears to be many feet higher than Harlem, and as [Buckanchans] Island tho’ not so high as Montresors is also higher than Harlem, our works with this advantage would I should think secure the Communication—Another Communication might I believe be Establish’d with Long Island from Frogs Neck, but as it may be interrupted by Vessels (Which from want of Anchorage Can not happen at Montrezanes) & is more Remote from Brooklyn it ought only to be held in secondary Consideration: The Distance from that part Long Island opposite Montrezanes & Buckenens is I believe about fourteen miles, it is rendered thus long by the intervention of Newton & Buchwiths Inlets. I am not well enough acquainted with Long Island to know Whether the Distance may be Shortened By Bridges. If (as in the 2d Quere is suppos’d) the Enemy should lose their superiority by Sea yet keep possession of the Harbour I should not be for any great diminution of the number of Men mentiond above, for tho’ in that Case their Attention and perhaps in some measure their Force might be more Divided yet as our communications Would be as various & must still be preserved by our selves very nearly the same number of men in my opinion would be requisite.

If the Enemy as the third proposition sets up should lose the superiority by Sea & also the possession of the Harbour, so many of our Communications would be secur’d by Ships and the Enemy would be assailable at such a variety of points, that I think a fourth of the men mention’d might be spared.

As our Mode of Attack and our lines of Communication would be the same tho’ the Enemy should not be Reinforced Either from the southward or from Europe, the Answers to the former Queries apply to the last, with only this Difference, that as the Force to oppose, will not be so great, that to assail may be proportionably lesson’d. The Militia Demanded of the states should be as Stationary with us as possible as they indubitably grow better by service, and as states I believe seldom come up to, and never Exceed the requisitions made of them, perhaps it might be expedient to request more than we really want. Upon the wholeSir I think that with proper military Endowments & with the number of men I have mention’d, New York, however Difficult, is attainable in Either of the Situations set fourth in the Queries. At the same time, the Reasons so judiciously given by your Excellency induce me to concur with you in opinion that desirable as the object truly is, it ought not to be Attempted but with great caution & probability of succeeding. I have the honor to be with the greatest Respect Sir your Excellency’s most obt hum. servt