Littlepage had an acrimonious parting from Jay in 1781, and after living as soldier of fortune for several years, he was eventually able to secure a position at the court of Stanisław II August of Poland. He sought an official letter of recommendation from the Congress for this situation, and Jay, by then the Secretary of State for Foreign Affairs, approved such a letter (although it was evidently never issued). Littlepage may have agreed to repay Jay’s numerous loans at this time, but in any case, Jay realized that he was in a position to do so. When Littlepage failed to reimburse him, Jay brought suit against him through Hamilton and Robert Morris. Littlepage was arrested in December 1785, but was released when Brockholst Livingston paid his bail.
Once freed, Littlepage issued a challenge to a duel, which Jay brushed aside, and then attacked his former benefactor in a series of letters in the New York Daily Advertiser. He then sailed for Europe, leaving Livingston liable for his debt. Whether the suit was settled by legal judgment or familial or other extralegal intervention is not clear. For his part, Jay feared that Littlepage’s actions could have been in service of a foreign power, and he wrote a pamphlet about the situation, Letters, Being the Whole of the Correspondence between the Hon. John Jay, Esquire, and Mr. Lewis Littlepage (New York, 1786), copies of which he sent to John Adams, Thomas Jefferson, and George Washington.
In the present draft, Hamilton avoided even mentioning Littlepage’s name, something he was unable to do in the version sent to Jay.
“I this morning received your letter of yesterday.
“I have seen with [word scored through] pain the progress of the transactions which have excited irritations between Mr. Livingston and yourself, and as my dispositions to both, in whatever I have had to do with the matter, have been friendly, I should with reluctance do any thing, that might affect either, further than a regard to truth and propriety should make it a duty.
“I can however have no scruple about stating what passed between Mr. Livingston and myself, shortly previous to your issuing the execution against him, which indeed was the principal thing, in which I had an agency relating to the subject of your Inquiry.
“In consequence of conversations with you and Mr. [Robert] Morris—meeting Mr. Livingston near the exchange, I introduced to him the Subject of your suit on the recognizance of bail; observing to him, that it was a pity the affair could not be concluded in a manner that would satisfy both parties. To this he replied that he had offered certain notes of persons of undoubted sufficiency, with his own indorsement, in satisfaction of the demand which had been refused by you—that he was now ready to assign or deposit a bond for a greater sum from General Schuyler to Mr. [Samuel] Loudon [publisher of the New-York Packet]. I answered in substance that I had heared of his offer and your refusal—that I did not think he could complain, because you were not willing either to transfer the debt or to take the trouble of collecting it from others, that as to General Schuyler’s bond, the same objection would occur, and indeed I could not with delicacy undertake to propose any thing about it—that I was however authorised to say, on your part, that there was no desire of precipitating him in the payment of the money—that what was chiefly wished was to obviate the necessity of any further proceedings on the judgment and to ascertain a period, at which it would be convenient to him to pay—that for this he might name his own time and his note, or even his assurance, would be taken—that in saying this I took it for granted he would not be unreasonable. Mr. Livingston utterly declined putting the matter upon this footing; saying that if you would not accept the offers he had made, you might do as you thought proper upon the judgment.
“This is the substance of what passed between us. I shortly after communicated to you my proposal and his refusal, and I understood, in a few days after, that an execution was issued.”
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