if Madison was a Federalist, why did he side with Jefferson in the Virginia and Kentucy Resolutions?

Answer 1

You misunderstand the use of the term "Federalist", and how it changed in the 1790s. But also, there is evidence Madison may have moved a bit in his positions under the influence of his good friend and fellow Virginian, Thomas Jefferson, AND in the political struggles that developed in the 1790s

To begin with -- in 1787 Madison supported the newly written Constitution (a document to which he contributed much --his own plans and compromises he helped broker). As a result, he worked hard to secure its passage. His efforts included assisting New Yorkers Alexander Hamilton and John Jay write a series of articles to explain it and "sell" it to the New York audience. Together these became known as the "Federalist Papers", because they argued in favor of the federal form of government represented by the Constitution.

At this point ALL who fought for ratification were called "Federalists". Opponents of ALL sorts were "Anti-Federalists" (a very diverse group, with different reasons for their opposition).

In one sense "Anti-federalists" died out once the Constitution had been ratified. But the former opponents went different directions. In any case, most accepted what majorities in their various states had decided on the matter.

But as the government actually took shape, the policy preferences led a significant group to oppose the policies of the Washington administration, and esp. of key leaders like Alexander Hamilton, who argued for a VERY strong central government. These folks began to work together and organize into "clubs" and into a separate party that usually called itself "Republican". (The local clubs had a variety of names, including "Democratic-Republican" club.) At the national level the most prominent leaders were Jefferson in the Washington cabinet and Madison in Congress. Note that this group was especially strong in the South, though there were also significant groups in Pennsylvania, and in New York (the latter led by the Livingstons, the Clintons and Aaron Burr).

As you noted, Madison and Jefferson were basically on the same page (often Madison acted as J's "lieutenant" in Congress)., including in the resolutions you mention. It is interesting, though, that if you look at what each contributed, Jefferson's actual view (on what ultimately became "nullification") was somewhat stronger than Madison's. This may reflect M's greater caution, or perhaps be one of those signs that he was a little closer to the OLD Federalists than Jefferson ever was.

Answer 2

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