Is it as simple as Madison understanding the need of a Constitution, but then being scared of it's unintended consequences (growing government power, etc.)? Did Madison later regret his Federalist stance? Thanks for any comments.
The country was in an entirely different place when Madison pushed for ratifying the constitution and when Madison helped draft the Virginia and Kentucky resolutions. The constitution had exposed fundamental issues of political theory and tradition in the American political elite, and the arrangement of federalists and anti-federalists drew the lines quite clearly. To put it clearly and superficially, federalists were in support of a government capable of maintaining its own integrity through the ability to legislate, tax, and conduct military affairs for the benefit of all, without subservience to local matters. Anti-federalists believed that allowing a federal authority to soak up those powers was, at best, a slippery slope toward legalized tyranny.
Federalists believed that the anti-federalist goal were eradication of federal powers, and anarchy based on mob rule (which was a legitimate, if somewhat exaggerated, fear, but that's not speaking to your question). Anti-federalists and their later spiritual successors, the Democratic-Republicans, believed that Federalists wanted to centralize power in the hands of a new monarchy in all but name.
The ratification of the constitution didn't really the settle those issues, and after a few years, two capital-letter political parties formed: the Federalists and the Democratic-Republicans. It should be noted that the parties had been more or less congealing since before the constitution, but a number of crises following ratification jostled them from loose affiliations to parties in the sense that we know them today.
I'm going to concentrate on just one or two issues for the sake of brevity, but know that even today, 1790s American politics are divisive and subject to distortion and misunderstanding.
The first crisis is the Whiskey Rebellion. Though trouble had been brewing for quite a while, the Whiskey Rebellion became widespread in 1794, forcing the federal government to get involved to put an end to it. The rebellion was concurrent with the Northwest Indian War (itself another focus of political division), and together, these crises strained the legal limitations of the government's ability to use force both on external enemies and internal insurrection.
Both parties, or at least the loose collection of powerful men who would eventually become the parties, saw entirely different things when they looked at the rebellion. To anti-federalist/Democratic-Republicans, they saw (somewhat exaggerating here) an oppressive federal government taxing hard-working citizens to benefit wealthy bankers and merchants. Federalists, on the other hand, saw Democratic-Republican schemers taking advantage of angry people and fomenting an insurrection bent of overthrowing the government and rolling back the constitution.
These are two completely irreconcilable points of view, and both sides were too suspicious of the other to act decisively. Washington was pressured by Hamilton to quash the rebellion instantly and with force, and although Washington was somewhat in favor of a quick resolution, he was understandably reticent to raise up and army and go after the rebels.
Partly, this had to do with the decentralized makeup of the American armed forces at the time. There was a small standing army, but it was largely out west involved in the NW Indian War, and recalling them to shoot at farmers was not possible or desirable. Washington was forced to rely on local militias, but the biggest issue was that the local militias were strongly pro-rebel, so the forces would necessarily have to come from other states. This agitated the issue of legal use of force and the federal governments rights in that area. A similar problem had happened earlier, during Shays' Rebellion in 1787, when militiamen had actually broken ranks and joined the rebels rather than engage them.
Washington didn't want that, knowing that any half-hearted attempts to stop the rebellion might just strengthen the rebels. Complicating matters further, Pennsylvania Governor Thomas Mifflin flat-out refused to allow Washington control over the Pennsylvania militia at first. Pennsylvania Chief Justice Thomas McKean put it bluntly: “The employment of military force, at this period, would be as bad as anything the Rioters have done - equally unconstitutional and illegal.”
To be clear, McKean and Mifflin weren't necessarily anti-government radicals, but they understood that there was a need for caution and for coalition-building in the federal approach to the rebellion. Although it may have been true that some anti-federalists were using the rebellion to fuel an anti-government fervor, it was not as widespread or as dangerous as many Federalists believed.
Washington's approach was slow and methodical, which accomplished two things: first, it allowed the rebellion time to lose its luster, and second, it allowed Washington to demonstrate that his goal wasn't despotism, and that he could handle the radicals in his party who were arguing fervently for military intervention. He was able to gain support from those who had initially opposed him, and eventually the whole thing was settled without bloodshed. A multi-state militia marched against the rebels, who largely faded away in front of the advance. There was no dramatic showdown or anything. It was quite bathetic.
But again, it set up the two parties, and their main concerns as they regarded their political opponents: Federalists believed, with some justification, that the Democratic-Republicans were a bunch of anti-government radicals and Democratic-Republicans believed, again with some justification, that Federalists were interested in using crises to elevate state power to enrich themselves.
Of course, both views are caricatures, but there were those on both sides who fit the description, so to speak.
Things got pretty vitriolic, even when Washington was the president. After Adams was elected, the Democratic-Republican side picked up speed and support, and Adams was in no way as revered or respected as Washington. Adams' political beliefs, in stark opposition to his bellicose personality, were fairly traditional in the sense that he strongly believed in constitutional balance, and was generally uninterested in the collection of power for its own sake.
Personal beliefs aside, the 1798 crisis brought many of the partisan issues to a head. The French Revolution was indicative of what a government ruled by mob force was capable of, and Democratic-Republican sympathies with the French people were appalling to many Federalists, which were read a support of violent overthrow of the government.
Democratic-Republicans, meanwhile, decried the violence but supported the overthrow of a despot, which meant that the Federalist reaction, their preparations for possible war and for the passing of the Alien and Sedition Acts, was indicative of their inherent tyrannical leanings.
I had to cut this because I reached my text limit. More below!