From Isaac Winston
Auburn Decr 26th 1805
At no time since I have had the Happiness of being acquainted with you,1 have you had it in your power to render me so essential, and important a service, as at the present moment. For some Time past, I have been Writing to Colo. John Nicholas about a Tract of Land he offers for sale near F.burg,2 but have recd. no Answer. I have thought it best therefore, that Walter should in person negotiate the Business, and make the purchase—but both himself, and me, being Strangers to Colo Nicholas, I would take it extremely kind of you, to write to him, both of Walter, and myself.
Under existing Circumstances, I can only offer Walter as my Security in case of Purchase. As he possesses an Estate in Land, and Negroes, in his own Right, he could only by a Stranger be tho’t objectionable, but possibly, Colo. Nicholas might think otherwise. Should this be the Case, a delay must unavoidably ensue, and there being several Gentlemen, who talk of purchasing the Land, I might, from this Circumstance be disappointed I anticipate a difficulty too, which may arise from another Source—Ample as my Funds are, Colo. nicholas, from the View I have given of them, may in some respects think them Objectionable—now my Dear Sir, as I wish to be guarded at all points, I will ask the Favor of you to say to Walter, whether you would have any Objection to joining us in Bonds given to Colo Nicholas, and afford me pecuniary aid, if in your power, in the Course of the next Year—these Favors, I ask in Confidence of your Friendship, and would avail myself of, in Case of absolute Necessity only. To me, they might be great, as your Name alone, thus mentioned, would have more weight, than every thing I could possibly Write on the Subject to Colo Nicholas.
You will observe in my Instructions to Walter, the mention of Chewing Tobo. This is an article above all others, I wish Colo. N. to receive in paymt. as I have had some dealings with you in this way, I would be much obliged to you to, give Walter a Memo. of the 4 Barrels, and three Boxes, which you obtained of me, Stating the Cost of it, which was 2/ pound, and the Price it brought you, which I have been informed, for the first 2 Bls. delivered, was 3/ M.Currency.
I had for a great length of Time, been under great uneasiness, and suffered the most painful anxiety on account of your precious, And my ever beloved Dolley, but rejoice now, in having the power of congratulaling [sic] you on her Recovery—an Afft Remembrance to her, and all Frends, if you please, and be assured of my Sincere, and unalterable Affection
RC (offered for sale by Historical Collectible Auctions, Burlington, N.C., 24 June 2004, item 436). RC cover marked “W Winston”; docketed by JM.
1. Isaac Winston was married to Dolley Madison’s maternal aunt, Lucy Coles Winston. Walter Winston was one of their sons (Glossary, DMDE).
2. Winston probably referred to John Nicholas of Geneva, New York, who had advertised for sale his property in Stafford, Virginia, before he moved out of the state in 1803 (Fredericksburg Virginia Herald, 18 June 1802; PJM-SS, 6:271 n. 2).