Shays' Rebellion (pictured above is a depiction of the fire-fight at the Springfield Arsenal in early-1787) was still not only a fresh memory, but it had hit a nerve on the 50+ delegates, in that it raised the specter of class warfare in America (e.g. all the Massachusetts politicians that supported the tax increases and military response to the rebellion were voted out of office). To
James Madison, Shays' Rebellion was a major symptom of what was wrong with the Articles of Confederation (A of C). And, to Madison's absolute horror, some of the rebels even won elected office in Massachusetts.
The delegates at the Constitutional Convention hated paper money, and most, if not all, saw massive government debt as a catalyst that could cause social upheaval. For the delegates, a new government was needed to protect property, raise desperately needed revenue, and most of all to Madison, discipline rogue state legislatures.
The most difficult aspect of the convention to enforce was preserving the secrecy of the proceedings. It was decided that nothing could be published or discussed with non-delegates; even correspondence (letters) were included. On 29 May 1787, Edmund Randolph (Governor of VA, and the "Voice" of the VA delegation) was the first speaker. Randolph focused on the need for greater national security against a foreign invasion. Then, after presenting a mild persona, he introduced the Virginia Plan to the Constitutional Convention.
The VA Plan also had members of the Executive and Judicial branches chosen by Congress; the Chief Executive would serve a single term. Madison also insisted that Ratification of the future Constitution be conducted by specially-called state conventions, rather than state legislatures. One of Madison's main goals of the convention was to limit the influence of state legislatures on national policy.
The VA Plan's major weakness was that it only addressed the "shenanigans" of the state legislatures to the proposed national government; there was no reciprocal protection for the states against the national government. Also, under the VA Plan, Delaware would have a 1/90th share of representation, while Virginia and Pennsylvania combined would have 1/3.
Madison's main problem at this point in the convention was his lack of sympathy for the small states. He viewed states such as Rhode Island as holding the interests of the nation, and especially those of Virginia, hostage in the A of C. But what was really eroding Madison's influence in the convention was his insistence on his "Absolute Negative" (which would make the Senate the ultimate authority under the Constitution, able to discipline state legislatures); despite, or perhaps in spite of, his constant insistence, the "Absolute Negative" proposal was defeated 7 to 3.
What was new was a proposal that the Southern states pay taxes on 3/5's of their African slave population for representation, which was mostly posturing since no one at the convention really anticipated any meaningful revenue from the new tax. On 16 July 1787, the Connecticut Compromise was adopted; the VA Plan coalition met, but it was clear that all their momentum was lost.
After all his preparation for the convention, Madison had seen most of his ideas rejected in only six weeks. To Madison, the worst development was that Senators would be the pawns of the state legislatures. Some delegates left the Constitutional Convention after the Connecticut Compromise, but not Madison, who regrouped and refocused his efforts. For the remainder of the convention, Madison did his best to reduce the power of the Senate. Madison looked to the House, and the Executive & Judicial branches to diffuse the power of the proposed Senate.
To Madison, that meant that too much power rested in the Senate; ironically, it was Sherman's revision that suggested that the House of Representatives decide the Presidential Election if the Electors could not, with each state's Congressional delegation counting as one vote . . . Sherman's revision passed by a vote of 10 to 1 (pictured: a dramatization of the Signing of the Constitution).
Madison now focused his attention and energies on vesting as much power as possible in the Executive, based on what had been decided in the convention. To Madison, the Presidential veto represented at least partial success for his defeated "Absolute Negative". However, Madison failed in his attempt to require a 3/4's majority in both houses of Congress to override a veto . . . he had to be satisfied with a 2/3's majority. But Madison was pleased that the President had more "latitude and discretion" than the other two branches.
George Mason and Edmund Randolph were so dispirited that they refused to sign the Constitution. Randolph wanted the state conventions empowered to add amendments, while Mason loudly called for a 2nd Constitutional Convention (Elbridge Gerry was the third delegate that was present on 17 September, 1787, that didn't sign). For those that did sign the Constitution, their experience was far more wearisome than glorious. Madison saw the President as the only vehicle in the Constitution that could be in line with Virginia's interests; Madison wanted to make sure that Virginia would remain the most preeminent state in the U.S.
Madison succeeded in having the A of C send copies of the proposed Constitution to each state without a direct endorsement, or offering any proposed amendments. Madison also stood firm that state conventions should ratify the Constitution, not the state legislatures. Madison wrote Jefferson (who was still in Paris), expressing anger and frustration with the convention; he thought that the new government was far-too weak . . . soon, Jefferson, and even Madison, would view the new federal government under the Constitution to be too powerful at the expense of the states, especially towards their beloved Virginia.