Anti-Federalists, as a general rule, did not support the power of the proposed Central Government to tax individuals directly.
In his “Number One” of 18 October 1787, Brutus warned that the power to tax “connects with it almost all other powers, or at least will in the process of time draw all others after it.” And in his “Number Eleven” of 31 January 1788, he declared that… “the two most important powers committed to any government, those of raising money, and of raising and keeping-up troops.”
The Federalists, on the other hand, supported the power granted the Central Government in the proposed Constitution to directly tax State citizens.
Patrick Henry, to put it mildly, was against the granting of this new power… “I will never give up the power of direct taxation but for a scourge,” he proclaimed in his speech of 7 June 1788. Henry felt that each State should decide how to come up with its share of funding for the General Government “in the most easy manner for our People.” He begged his fellow statesmen, “I beseech Gentlemen, at all hazards, not to give up this unlimited power of taxation.”
The Massachusetts Convention of 7 February 1788 agreed with Henry, and declared its support for a Constitutional Amendment proclaiming that Congress will… “not lay direct Taxes but when the monies arising from the Impost and Excise are insufficient for the public exigencies nor then until Congress shall have first made a requisition upon the States to assess levy and pay their respective portions of such Requisition agreeably to the Census fixed in the said Constitution; in such way and manner as the Legislature of the States shall think best.”
Hamilton was one of the most realistic Founders when it came to matters economic and militaristic. Writing in Federalist #35, he informed his readers that, realistically speaking, the Central Government would not always be able to support itself merely by the imposition of Impost and Excise taxes. In cases of predicted shortfall, it “would frequently be tempted to extend these duties to an injurious excess.” But such “exorbitant duties on imported articles would beget a general spirit of smuggling” and prove counterproductive. “It might be demonstrated,” said the most financially savvy of the Founders, “that the most productive system of finance will always be the least burdensome.”
Plus, wrote Hamilton in Federalist #21, there really is no objectively fair way to tax the States, so it’s simply more practical for the General Government to raise its own funds directly. As Hamilton stated in his lawyerly fashion in Federalist #31… “as theory and practice conspire to prove that the power of procuring revenue is unavailing when exercised over the States in their collective capacities, the federal government must of necessity be invested with an unqualified power of taxation in the ordinary modes.”
In Federalist #32, Hamilton wanted to make it clear that the Federal power to tax would not infringe upon each State’s own taxing powers… “I am willing here to allow, in its full extent, the justness of the reasoning which requires that the individual States should possess an independent and uncontrollable authority to raise their own revenues for the supply of their own wants” […] “with the exception of duties on imports and exports.”
But Hamilton was adamant that the States must be willing to share with the Federal Government the power of direct taxation. Otherwise, he writes in Federalist #33, “the only admissible substitute is an entire subordination, in respect to this branch of power, of the State authority to that of the Union.”