You will not be surprised when you see your name at the head of a letter. The situation in which you have placed your self as the expectant of executive honors, renders your character, a proper subject of scrutiny, and you must have calculated, on receiving applause or condemnation, according to the light in which your conduct was viewed. The former has been lavishly bestowed; the latter, I feel most unwilling to express. But, sir, I am one of the millions interested in your prospects, and I have doubts respecting you, which mar my pleasure in contemplating you as the future chief of our nation. I will not apply to either Marcus or Tullius--their laboured sophistry and verbose zeal are illy calculated to satisfy my anxiety. Do not think, however, that I have any peculiar interests or selfish views before me. I am not loaded with present honors--a greedy expectant of patronage--nor a laborer for literary fame. My age and my situation, alike unfit me for either.

A President of the United States should be a person of eminent talents, of great political sagacity. He should be capable, not only of theoretical but of practical excellence in the science of politics--capable of developing the effects of principles, adapting them to the state of society, pursuing and supporting them with the perseverance of integrity and conviction. I do not believe you such a man. The history of your life does not justify the belief. That you possess much virtue, must be evident--but perhaps we may discover that it is of that unsuspecting, pliant kind, which is better fitted for the farm and the fire side than for the scenes of public life.

You have made frequent displays of genius and proved yourself to be capable of supporting an opinion, with energy and elegance. After discovering the truth, or being directed to it by experience, you are one of its ablest defenders. But unfortunately you have too often discovered it, when for ought you could do, it was for ever too late. Do you suppose the principles you advocated at the formation of the constitution of the United States calculated at this moment to secure the confidence of the people? Were you then the adherent of principles you now profess? The memories of the people are not treacherous, nor their confidence in political conversions, hasty or unlimited. Your efforts on that occasion were great, but were they great in support of those sentiments, which republicans love? You shine with considerable brilliancy in the Virginia convention--you perhaps merit much of the applause arising from the formation of many parts of the constitution, but were they its republican features for which you stood sponsor? One would imagine not, from your public speeches and your essays in the Federalist. With all the alterations and amendments to which that instrument has been subjected and which you opposed, we have seen, that in too many instances it may be readily converted in practice; to something widely different from a republican constitution. Should you not, if your discernment be not too highly applauded, have foreseen these effects, & instead of opposing, have exerted your self to add new guards against abuse? Or does your merit lie, in forming theoretic beauties and practical incongruities? Are you certain that as President you will not find cases where something more than theory will be required? You will not shelter yourself behind the excuse, which Marcus has erected to save you. You will not tell me that we have only seen what may be made of the constitution in the hands of a skilful artist. For your discernment, and skill in political science, have been praised. Besides, you were told with the energy of inspiration, what a "skilful artist" might do with it. The ease, with which it might be perverted, gained Hamilton’s support and was one of the strongest objections to its ratification. Yet you braved the danger, you thought it perfect without amendments. And I am at a loss to discover how he can be proved to be the very best person to manage it, who saw no necessity for many of its parts. The mariner who heedlessly or ignorantly runs into danger will scarcely be trusted, when a more provident pilot can be procured. Ask your memory if your opponent be not such an one.

This is not the first time that you have had the honor of a contest with James Monroe. Your popularity and talents have before been tried against him--and you may possibly see the very same result. Does the recollection of the principles on which you contended, afford any gratification to your republican feelings? Do you feel the glow of conscious satisfaction, at the superior accuracy of your judgment? At the time to which I refer, you had no longer the plea of disunion as the consequence of the measure, your opponent advocated. The horrors of anarchy no longer haunted your imagination--your talents had fair scope for operation. And whose principles have since been declared to be correct? The decision of the nation has been audibly pronounced. Why then do you claim so decided a superiority of talents? It is not for the sake of contrast alone, that I remind you of these times and these matters. They prove, either that your penetration does not merit the eulogies it receives, or that you were not at all times such a republican as merits trust. You have, ’tis said, the honor of speedily changing your course. Desertion of error is ever meritorious. But why did you change? Did you see the correctness of your former opponents? Did you begin to discover the true objects of your fellow laborers, Hamilton &c. Or did you see no prospect of climbing that ladder to whose top you are now so hastily mounting? We would be apt to conclude that it was the latter, since those mens’ principles had been well known, from the time that Hamilton offered his monarchical project in the convention. And yet you condescend to become the political associate, the fraternal partner of those men in the propagation of a creed! Your services in Congress were commendable--but why did you retire in despair? You certainly saw some danger in the course then pursued, or you would not have opposed it. Your character forbids us to harbor the idea that you would not swim with the tide, as long as your conscience would permit you. Was it becoming in you to shrink from the danger which you perceived before you? Is it the part of the patriot to see his country laboring and to cease to afford aid while a glimmering of hope remains! Or will you rely on Marcus to make your excuse? Marcus is singularly unfortunate. He would put such reliance on the progress of opinion, as to render useless any accelerating efforts. His plea accuses the laborers in the republican cause with a stupid and unnecessary perseverance. Their work would have been performed by the "progress of opinion" without their aid. What short-sighted men they must be, not to have discovered this truth and to have spared themselves the labors they underwent. Does your champion rely on your own example, to prove that a change of principle must inevitably follow from the state of the nation at that time? Did the conviction, that your exertions were not needed, arise from this example and experience? The calculation terminated well, but does little credit either to your wisdom, your patriotism, or your perseverance. It is better fitted to form a cover to disgust, irresolution and despair. Or do you prefer the other excuse of private and professional interests? Are they to be preferred to the public good? If so, why then do we so soon see you at the Federal City? Was your professional character so soon established, your fortune so soon mended? You have a competitor whose professional reputation has been neglected, whose fortune has been destroyed, sacrificed in the public service. Why is the Secretary-ship so long borne, when the responsibility of a representative was a little time ago, too heavy a burden? Marcus should not have forgotten, that the Presidency was in view.

There is another part of your conduct that I cannot recollect with any considerable degree of satisfaction. Wny is your house the peculiar and favored resort of federal worthies, and your office filled with federal men? Does it arise from partiality to them? From a disposition which can readily associate with the most obnoxious materials, party can afford. From a culpable irresolution which fears the performance of an invidious duty--a distinction between parties--a preference of the friends of the administration? I can conceive no other motive. I leave you to your choice. Either of them should be equally injurious to your pretensions. Mr. Brent will excuse me for naming him. It cannot be from disrespect to him as a man. His fame except as a federalist has not been loud enough to reach me. Why was he selected as the object of patronage? Were his talents so admirable? Was there not one of your own party, in whom you could confide? Or are there, less manifest, but more operative reasons behind the curtain? Did you seek the popularity of his country, his friends and his party? Or was it because he was the distinguished pupil of Alexander Hamilton? Had I remembered that you were that gentleman’s associate in the labors of the Federalist, I might have spared you these questions.

You have often been charged with partiality to Yazooism. Your report certainly looks something like it. But I believe you too honest, far too honest, to be interested in that hideous speculation. Your advice on the subject I take to be the dictates of your judgment--But it evidently is a judgment warped by feeling, fearful of dangers, and timidly shrinking from right lest it should encounter difficulties. You see corruption stalking before you--you detest the object, but you would buy its peace rather than oppose & subdue it. You would give a premium to infamy, to ensure present quiet, rather than affix the proper mark upon it, lest it murmur. The motives of your conduct cannot meet my approbation--yet, are they motives and feelings which seem to have operated through your whole life. And do you believe that a temporising policy is the best policy? Do you esteem it correct to pardon and conciliate corruption when it is noisy? I shudder at the prospect of an executive, constituted as ours is, who professes such a belief. Republican principles and the good of our country know not how to temporize. They know no affinity to corruption. They cannot exist one moment in the air which it pollutes.

It is painful, but it is necessary to remind you of a fact which does little credit to your heart or your understanding. It was not very long since that we had an ambassador in Europe who was odiously criminal. This ambassador had something to do in the purchase of Louisiana, that is, he received the credit of assisting in the negociation, because he had not ability to frustrate it. When his associate, one of the first ornaments of our country communicated to you at considerable length, the multiform criminality of this man, you replied to this effect--"Your communications have been received--you may rest satisfied that you will receive your full share of credit for the Louisiana purchase." Does such a reply need a single comment? If you are not far more depraved than I suspect you to be, at least a momentary blush will color your cheeks when you think your fellow-citizens are reading this answer to a lengthy, a disinterested, an important communication. Was it envy, was it malice, that dictated these words? Was it such a communication as the interests of your country demanded? Was it paying to the man, to whom it was addressed, the respect due to the station which he held? In what feature of his life did you see a foundation for so damning an insinuation as your note conveys? Or did you see in him the future rival, the dangerous competitor for future honors? Are we to read in it the movements of your mind? Can it be the expression of your feelings? Short as it is, your friends may read in it a volume of testimony. I look with anxiety to the time when the writer of such a note is to guide the destinies of my country.

When sometime after this event, a gentleman offered to substantiate this minister’s baseness, you replied as if ex officio, that the executive would have nothing to do with the matter. Why was this? I am perplexed and confounded in the attempt to trace this reply also to its cause. Was the matter of so little consequence to the government, the honor, and interests of the country? Are we to trace this again to your want of decision and courage? Or is corruption so dangerous to you that you fear to have it started? Pardon the question. Your conduct is so inexplicable, that it is not surprising the idea should be suggested. But we will repress it. Your motives were probably less opposed to an honest, more consonant to an ambitious mind, looking forward to a Presidential election.

Will you also explain, why our commissioners under the Louisiana Convention, were embarrassed for support? I should be fearful to trust the memory which could, for such a length of time, leave such characters destitute of the funds voted by their country and drawn from its treasury. Are you not suspicious that your country will attach something more than forgetfulness to this circumstance, until it is explained?

The administration to which you belong has met with some opponents, where, perhaps, they were least to be expected. It is true, they have received the disapprobation of a majority of the republicans. I do not rank in the list of their warmest friends. And yet perhaps they have better causes of dissatisfaction than their country is aware of. If I do not err in my calculation, James Madison has been in no small degree influential in converting his own enemies into opponents to the administration. As I have observed the occasional agitations which have been felt in public matters, the cloud has seemed to rise from you and to burst about you. At some other time the reason may be probed. Marcus indeed tells us, that you never made an enemy⟨,⟩ that only those of the administration have been marshalled against you as one of its members. But Marcus is to be excused; he feels a sympathy for you. The force of this feeling is great in the human breast; and there is too striking a similarity in the conduct, character and habits of yourself and Marcus, for him not to experience toward you, the most powerful emotions. Memory seems to add peculiar energy to his zeal. His portrait often obliges the enquiry whether J. Madison was the only object before him at all times not because he has pourtrayed himself, but because he has so labored to conceal certain facts and certain traits of character.

My letter is finished. I do not promise myself much success from my attempt--My abilities do not warrant the expectation. But I love republicanism too well not to speak, when I believe, that if you are elected, your administration will be a palsying blow to it. You will not charge me, as your friends have before charged your opponents, with unfairness, and an attempt to spargere voces in vulgum ambiguas]. The doubts expressed are by no means equivocal. If they can be removed, I shall rejoice. If not, I like others, will prepare myself for that contest of opinion which must result from your election.