The time had, however, come at last when Clinton's right to continue as governor was to be contested. Hamilton's encounter with the New York opponents of the Federal Constitution had been vigorous and acrimonious. It was easy to stand with one's State in opposing the Constitution when opposition had behind it the powerful Clinton interest and the persuasive Clinton argument that federal union meant the substitution of experiment for experience, and the exchange of a superior for an inferior position; but it required a splendid stubbornness to face, daringly and aggressively, the desperate odds arrayed against the Constitution. Every man who wanted to curry favour with Clinton was ready to strike at Hamilton, and they covered him with obloquy. Very likely his attitude was not one to tempt the forbearance of angry opponents. He did not fight with gloves. Nevertheless, his success added one more to his list of splendid victories. He had beaten Clinton in his intolerant treatment of loyalists; he had beaten him in obtaining for Congress the sole power of regulating commerce; he had beaten him in the Philadelphia convention called to frame a federal constitution; he had beaten him in a state convention called to ratify that constitution; and now he proposed to beat him for governor in a State which would have great influence in smoothing the way for the new federal government.

After the close of the Revolution, there had been local parties in the various Stales, divided on issues of hard and soft money, on imposts, on treatment of Tories, and on state rights, and these issues had coincided in many of the States. During the contest growing out of the adoption of the Federal Constitution, all these elements became segregated into two great political parties, those who supported the Constitution being known as Federalists—those who were opposed to strengthening the bond between the States being called anti-Federalists. The latter were clearly in the majority in New York, and Hamilton rightly inferred that, notwithstanding the people, since the adoption of the Constitution, manifested a disposition to sustain the general government, a large majority of freeholders, having heretofore supported Clinton as a wise, patriotic governor, would not now desert him for an out-and-out Federalist. To meet this emergency, several Federalists, at a meeting held February 11, 1789, nominated Robert Yates, an anti-Federalist judge of the Supreme Court, hoping thus to form a coalition with the more moderate men of his party.

In support of such politics, of the doubtful wisdom of which there was abundant illustration in the recent unnatural coalition between Lord North and the brilliant Charles James Fox, Hamilton wrote to his friends in Albany that in settling upon a candidate, some difficulties occurred. "Our fellow citizens in some parts of the State," he said, "had proposed Judge Yates, others had been advocates of Lieutenant-Governor Van Cortlandt, and others for Chief Justice Morris. It is well known that the inhabitants of this city are, with few exceptions, strongly attached to the new Constitution. It is also well known that the Lieutenant-Governor and Chief Justice, whom we respect and esteem, were zealous advocates for the same cause. Had it been agreed to support either of them for governor, there would have been reason to fear that the measure would have been imputed to party, and not to a desire of relieving our country from the evils they experience from the heats of party. It appeared, therefore, most advisable to elect some man of the opposite party, in whose integrity, patriotism, and temper, confidence might be placed, however little his political opinions on the question lately agitated might be approved by those who were assembled upon that occasion.

"Among the persons of this description, there were circumstances which led to a decision in favour of Judge Yates. It is certain that as a man and a judge he is generally esteemed. And, though his opposition to the new Constitution was such as his friends cannot but disapprove, yet, since the period of its adoption, his conduct has been tempered with a degree of moderation, and seems to point him out as a man likely to compose the differences of the State. Of this at least we feel confident, that he has no personal revenge to gratify, no opponents to oppress, no partisans to provide for, nor any promises for personal purposes to be performed at the public expense."[50]

To many the selection of Robert Yates seemed almost ungracious. The Federalists wanted Richard Morris, chief justice of the Supreme Court, who had encouraged the establishment of a strong government, and, as a member of the Poughkeepsie convention, had voted to ratify the Federal Constitution. Besides, he was a gentleman of the old school, of inflexible integrity, firm and decided in character, whose full, rounded face and commanding presence appeared to advantage among the stately and dignified personages who supported knee breeches and silk stockings, and displayed the delicate ruffles of a shirt under the folds of a rich velvet coat. Hamilton was fond of Morris, and recognised the justice of his claims. Their views in no wise differed, their families were intimate, and at the Poughkeepsie convention, after listening for three hours to Hamilton's speech, Morris had pronounced it the ablest argument and most patriotic address ever heard in the State of New York. But the great Federalist, determined to destroy Clinton, wanted availability, not fidelity, and so Morris declined in favour of Yates.

In everything Robert Yates was an anti-Federalist. He dressed like one and he talked like one. He had been an opponent of the Federal Constitution, an advocate of the doctrine of state supremacy, and an ardent supporter of the Governor. With Clinton's approval he had withdrawn from the Philadelphia convention when the majority favoured a strong government wielding supreme authority; with Clinton's approval, he had opposed the ratification of the Federal Constitution in the state convention at Poughkeepsie, and with Clinton's approval he declined to change his vote, although New Hampshire's action and Hamilton's speech had already settled the question of ratification. What Hamilton proposed, Yates opposed; what Clinton advocated, Yates approved. After the ratification of the Constitution, however, Robert Yates charged the grand jury that it would be little short of treason against the Republic to disobey it. "Let me exhort you, gentlemen," he said, "not only in your capacity as grand jurors, but in your more durable and equally respectable character as citizens, to preserve inviolate this charter of our national rights and safety, a charter second only in dignity and importance to the Declaration of our Independence."

Upon the bench Yates distinguished himself for impartiality and independence, if not for learning. He abated the intemperate zeal of patriotic juries, and he refused to convict men suspected of disloyalty, without proof. On one occasion he sent a jury back four times to reconsider a verdict of guilty unauthorised by the evidence, and subsequently treated with indifference a legislative threat of impeachment, based upon a fearless discharge of duty. He could afford to be just, for, like George Clinton, he had early embraced the cause of the Colony against the Crown. From an Albany alderman he became a maker of the State Constitution, and from a writer of patriotic essays, he shone as an active member of the Committee of Safety. Together with John Jay and Robert R. Livingston, he had obstructed the passage of Lord Howe's ships up the Hudson, and with General Schuyler he devised measures to repel the British from the northern and western frontier. He had helped to fix the dividing line between Massachusetts and New York, and, as one of the Council of Administration, he governed southern New York from the withdrawal of the British until the assembling of the Legislature.

Having decided to go outside his own party, Hamilton made no mistake in picking his man. If Clinton was the Hampden of the colonial period, Robert Yates could well be called its Pym. He had toleration as well as patriotism. But he also had an itching desire for office. Some one has said that the close connection between man and a child is never more clearly illustrated than in the joy and pride which the wisest statesman feels in the wearing of a ribbon or a star. It could not be said of Robert Yates then, as it was said, with good reason, six years later, that his desire for office extinguished his devotion to party and his character for political consistency, but it was openly charged that, upon the suggestion of Hamilton, he urged the grand jury to support the Federal Constitution in order to strengthen himself with the Federalists. Whether this be true or not, Yates' previous devotion to the anti-Federalist party set his present conduct in sharp contrast to that of other distinguished anti-Federalist statesmen of the time—to men like Samuel Jones and Melancthon Smith, who accepted the action of the Poughkeepsie convention, but supported George Clinton. "Men, not principles, are involved," they declared.

All that we know of Yates would seem to deny his surrender of principle, or his condescension to any act of baseness, to obtain office. It was indeed a question whether Clinton, or Hamilton through Yates, should control the state government; but the gubernatorial contest involved more than that. The new government, soon to be placed on trial, needed the help of sympathetic governors and legislatures, and Clinton and his supporters, forced to accept the Constitution, could hardly be regarded as its wisest and safest guardians. From Hamilton's standpoint, therefore, it was more principle than men. However agreeable to him it might be to defeat and humiliate Clinton, greater satisfaction must spring from the consciousness that while in its leading-strings, at least, the general government would have the hearty support of New York.

Hamilton's great coalition, intended to work such wonders, boasted many brilliant names. Of the younger men Robert Troup, of Hamilton's age, an early friend of Burr, took a most conspicuous part, while among the older members of this galaxy was James Duane, a lawyer of rare ability, the first mayor of New York, for ten years continuously in the Continental Congress, a man of great force, of large wealth, and superb character. He was in his forties when Hamilton, a boy of seventeen, won his heart by a single speech, denouncing the act of Parliament which closed the port of Boston. The most notable man in the coalition, next to Hamilton and Jay, was Robert R. Livingston, now Hamilton's devoted friend, before long to be his bitter enemy. He was still young, little more than forty, but in everything he was bold and skilful, vigorous as a writer, eloquent as a speaker, deeply learned as a jurist, and rich in scholarship. Of the same age as Livingston was William Duer,[51] who started at eighteen as an aide to Lord Clive in India. Duer was at one time the most useful man in America. Nobody could cheat him. As soon as Hamilton became secretary of the treasury, he made Duer assistant secretary, an office which he held with credit until 1790, when he resigned to become the chief of a ring of speculators, who, two years later, left him insolvent and in jail. Hamilton's coalition also furnished the only instance of the political association of himself and Burr, although Burr's support of Yates is said to have been personal rather than political. The story is that Burr, seeking admission to the bar after reading law less than a year, induced Judge Yates to suspend the rule requiring three years of study, because of the applicant's term as a soldier, a service that laid the foundation of a lasting friendship.