President Washington had announced his retirement from public life in an "Address of General Washington To The People of The United States on His Declining of the Presidency of the United States," first published in the Philadelphia American Daily Advertiser on 19 September 1796. Washington had originally written this farewell to be effected after his first term in office, but the rancor between Treasury Secretary Alexander Hamilton and Secretary of State Thomas Jefferson, as well as the growing rivalry of the political parties each represented—Federalists and Democratic-Republicans, respectively—induced him to serve a second term. No suasion, however, could keep Washington in office longer than that, and his farewell address, which was partially revised by Hamilton, led directly to the first contested presidential election in American history.
The Federalists, who counted Alexander Hamilton among their ranks, supported a strong central government and chose a ticket of John Adams of Massachusetts for president and Thomas Pinckney of South Carolina for vice president. The Democratic-Republicans favored individual state sovereignty rather than a powerful centralized government and chose Thomas Jefferson of Virginia and Aaron Burr of New York for the same offices. At the time, presidential electors each cast two votes, one for president and one for vice president, but the votes were not differentiated and the candidate with the most votes became president, while the runner-up became vice president.
Hamilton sensed in this flawed system an opportunity to deny the presidency not only to his bitter political enemy Thomas Jefferson, but also to John Adams, an acrimonious rival from the Washington administration. Hamilton schemed to have southern electors vote for Pinckney but to drop Adams in favor of another Federalist like Oliver Ellsworth, John Jay, Samuel Johnston, or James Iredell. When Hamilton's ploy was exposed, New England electors retaliated by not voting for Pinckney. The result of this internecine feuding was that John Adams was elected president, but the second highest number of votes—and the vice presidency—went to a candidate from the other party: Thomas Jefferson.
In the present letter, Hamilton surveys the state of play for the presidency, cynically deprecating Adams while repeatedly returning to the theme that "All personal and partial considerations must be discarded, and every thing must give way to the great object of excluding Jefferson."
“Our excellent President as you have seen has declined a reelection. Tis all important to our Country that his successor shall be a safe man. But it is far less important, who of many men that may be named shall be the person, than that it shall not be Jefferson. We have every thing to fear if this man comes in; and from what I believe to be an accurate view of our political map I conclude that he has too good a chance of success, and that good calculation prudence and exertion were never more necessary to the foederal cause than at this very critical juncture. All personal and partial considerations must be discarded, and every thing must give way to the great object of excluding Jefferson.
“It appears to be a common opinion (& I think it a judicious one), that Mr. Adams & Mr. Pinckney (late Minister in England) are to be supported on our side for President and Vice President. New York will be unanimous for both. I hope New England will be so too. Yet I have some apprehensions on this point, lest the fear that he may outrun Mr. Adams should withhold votes from him.
“Should this happen, it will be in my opinion, a most unfortunate policy. It will be to take one only instead of two chances against Mr. Jefferson & well weighed, there can be no doubt that the exclusion of Mr. Jefferson is far more important than any difference between Mr. Adams & Mr. Pinckney."
At this point in the letter, seven lines of text have been obliterated, likely by Hamilton himself, but possibly by his son, biographer, and editor John Church Hamilton. Taken in context with the next two paragraphs, which were supressed in John C. Hamilton's edition of his father's papers, the deleted passage must have been a severe attack on Adams, since the censored paragraphs offer a glowing endorsement of Thomas Pinckney:
“But on the other hand Mr. Pinckney is a tried Patriot, a man of irreproachable private character—a man of real good sense, not deficient in information, of consummate discretion, of conciliatory manners & temper, less en[?] but than any other man that can be brought forward to the violence of party passions—a firm friend to the Government, correct to our foreign relations, and of distinguished firmness of character.
“However we may wish Mr. Adam’s success, can we extremely regret if the choice should be happen to fall on Mr. Pinckney? Can it be a doubt than even at this risk it will be wise to take a double chance against Jefferson?”
“At foot is my calculation of chances as between Mr. Adams & Mr. Jefferson [this calculation is not in fact present]. Tis too precarious. Pinckney has the chance of some votes Southward and Westward which Mr. Adams has not. This will render our prospect in the main point, the exclusion of Jefferson, far better." Far from excluding Jefferson, Hamilton's "double chance" misfired, making him vice president and positioning him to capture the White House in 1800.
Hamilton concludes on a confidential note: “Relying on the strength of your mind I have not scrupled to let you see the state of mine. I never was more firm in an opinion than in the one I now express, yet in acting upon it there must be much caution and reserve.”
On 8 November 1796, Hamilton sent a brief letter to Jeremiah Wadsworth stating "A few days since I wrote you my opinion concerning the good policy of supporting faithfully Pinckney as well as Adams" (Papers, ed. Syrett, 20:377–378), so it seems likely that the present draft was for a letter sent to Wadsworth, a Hartford, Connecticut, merchant and politician who represented his state in both the Continental Congress and the United States House of Representatives.