The Wolfs–friend, if not the head, one of the most considerable Chiefs of the Chickasaw Nation is now in the City, at the instance and request of Brigadier General Wilkinson, who has intimated to me the expediency of securing his future good will and friendship to the United States by promising him an annual stipend.

It may be proper to observe on this occasion: 1st That there are in the Chickasaw Nation two parties, one strongly attached to the United States, at the head of which are Opiomingo & George Colbert; that the Wolfs–friend has always been considered, as opposed to Opiomingo, and his party and even to be a stipendiary of Spain, from which Court he is said to receive six hundred dollars annually. 2d. That the Chickasaw party friendly to the United States have aided us against the enemy Indians in our latest hostile operations against them under General Wayne. 3. That the Nation is connected with the United States by treaty, conformably to which they are intitled to receive three thousand dollars annually. 4th That there has been no stipend paid to any Individual chief of the party, friendly to the United States, other than his share of the 3000 Dollars paid according to the treaty, and such occasional presents as have been made necessary by particular circumstances. 5th. That the United States and Spain being at peace and the United States not intending to do any thing, on their part, to produce a different state of things, there does not appear any reason sufficiently cogent, why the Wolfs–friend should be more distinguished, than the antient adherents to the United States, especially as the measure might be attended with disagreeable consequences, should it come to their knowledge.

It is submitted therefore, whether it would not be less exceptionable, calculated to lay him under obligations to the United States: to excite in his mind expectation<s> of <future> further favours; and upon the whole best, to make both him and Colbert, each a present of one hundred dollars, in addition to the presents in articles of dress, which it has been usual to give to Indian Visitors.

It appears by letters from Lt. Colonel Butler and Mr. Walton, late Commissioners for treating with the Cherokee Nation of Indians, which I had the honour to submit, that these Gentlemen engaged to pay the Bloody fellow (a principal Chief of the Cherokee Nation) six hundred dollars, for his services in promoting the conclusion of the treaty, and by a letter from Capt. Butler (annexed), that they did not draw this money from Colonel Henley, Agent of the War Department in Tenessee, as had been first intended; but refered the Bloody–fellow to the Secretary of War, to prevent any knowledge of the transaction transpiring where it might be likely to be interpreted to his disadvantage.

I think it will be proper the engagement of the Commissioners, should be punctually and faithfully complied with; and shall unless it is your pleasure to order otherwise, direct the payment to be made, under the appearance of compensating him for his trouble, as a Commissioner for running the line established by treaty

The Wolfs–frend expects, and solicits an audience of the President at such time as shall be most convenient.

Mr. Israel Chapin, from Canandaigua, is now waiting at the seat of Government to receive for and convey to the Seneka Nation of Indians the Dividends upon the Bank stock, held in the name of the President of the United States for their use agreeably to treaty.

Inclosed is a copy of a letter to Israel Chapin dated the 11th of Octbr. ulto. and another of the same date, to the Chiefs and Sachems of the said Indians, which will serve to shew, what they expected, and what has been promised them.

An authority is necessary from the President to enable some person to draw from the Bank of the United States, as well the dividends which have accrued upon the said Bank Stock, since invested as aforesaid, as the interest upon the original sum agreed by treaty to be so invested from its date to its investment, and a small sum of excess of capital, if shall be deemed expedient to transmit whatever monies are now in Bank belonging to the Seneka Nation, by the hands of Israel Chapin, to be paid by him to the Nation.

The money in Bank which may be sent forward is the Dividend of July 1798 and January 1799—on two hundred and five shares, amounting to 6560 Dollars &’; Cash amounting to 1876 94/100 Dollars.

It strikes me that the most eligible course to give to this business would be for the President to empower the Treasurer, in his character as Treasurer for the Department of War, to receive this money of the Bank, subject to the warrants of the Secretary of War. By this proceedure the warrants and entries in the books will substantiate the whole transaction.

I have the honour to be with the greatest respect Sir / Your most ob st