The rapidly declining health of that excellent man Elias B. Caldwell rendering it almost certain that he cannot survive many weeks—and thereby render vacant the office of Clerk to the Supreme Court of the United States. In my old age and present poverty brought on me by my responsibilities for two imprudent and unfortunate Brothers for whom I have had to pay fifty thousand dollars my appointment to such vacancy is important to the comfort of myself and wife during the few remaining years of our Lives. From the knowledge which the Chief Justice & Judge Washington have [of] my character & sufferings—I have reason to hope a favorable decision from them. If therefore thro’ your and Mrs. Madison’s recommendation Judges Todd & Du Val1 could be induced to lend their support—I presume I might be chosen. I cannot permit myself to doubt that Mrs. Madison would be very happy to contribute every thing in her power, to render the evening of the days of her youthful friend now sinking in the vale of years comfortable.

Whatever measures which you may deem it proper to take to accomplish this object will be gratefully acknowledged by both of us.

I am sensible of the great delicacy in applying for an Office yet full. But it has become so universal a practice in our own & perhaps every other Country—that I trust you will excuse me—more especially as the event alluded to is as certain as what has not already happened can be.

Permit me to add that I shall if appointed cheerfully & liberally share the emoluments with the amiable & deserving son of Mr. Caldwell who has not yet arrived at age. With sentiments of unabated esteem, and constant prayers for the long continued happiness of Mrs. Madison & yourself—I remain your sincere friend & devoted Servant