[Free] Portland June 11. General Henry Knox New York [Administrative notations, lower right, written sideways: — No colter / answered No. 21 [undecipherable] / Rec'd [undecipherable] 1789] [mr Winslow] Portland June 10^th 1789 My Dear S^r I have been some time in a Dilemma about addressing You, upon a Subject which the real Desire to my Welfare have so heatedly suggested to me. Unaccustomed to soliciting favors, nought but my present precarious Establishment, and an ardent Desire to maintain Respectability in life — to bring forward my Boys with Reputation, and by a proper Education to fit them for [undecipherable] Society — could induce me to hazard the Reception You might give this application. My Situation in this Country, would make it convenient & peculiarly eligible, time, to act in some Department under the Federal Government, the necessary Appointments in the Revenue must be extensive. The several Counties of York, Cumberland & Lincoln will most probably fall under one District. The Collectorship & [undecipherable: Inspectorship?] by the Marsall Office are objects of Magnitude, and would with an approv'd Conduct, secure to the Possessor a permanent decent Living. I imagine some Friend of mine may have already address'd You, soliciting your kind Influence in my behalf; but my Apprehensions that You might think that such Business might interfere with my necessary Eastern Pursuits, led me to endeavor to obviate any objection [that] might arise upon that Consideration. I have no immediate Prospect of Advantage in the Country, and no Capital for Business, whatever is necessary to be done or attended to within the Patent, I may accommodate time to, without interfering with Official Engagements. The weighty Concerns of a numerous Family, require some more certain regular Support. From an unproductive Election Interest, I cannot at present obtain it. I look forward to the [undecipherable] who may make a happy Allotment there. The Attainment of my present Object would afford me a facility in the executing my Business, and a Spirit to [undecipherable], which I cannot exercise under the [undecipherable] of complicated Affliction. That I feel zealously interested in the Prosperity of the Federal Empire, You will not doubt. And I should with unremitting Industry & Energy execute the Duties of whatever Station, I may be appointed as to be placed in. You may be most perfectly assured, and that I should [undecipherable] observe that Strict Regularity & Punctuality indispensably necessary to the maintenance of Character. I must close by requesting the peculiar favor of You, if not inconsistent with any Prior Engagements, that You would use your Influence with your Friend in Congress, that I might have an Appointment in the Revenue Department, which would extremely oblige me. I pray You, my Dear Sir to make my most affectionate Regard acceptable to M^rs Knox, and believe me with profound Respect. Your Affectionate & ob^d humble Servant Sam^l Winslow