I think that one of the primary differences between Madison and Henry in their views of liberty exists in their classification of Federalist vs. Anti-Federalist. Madison was of the mindset that the new nation needed some type of structure and lawful order in order to prevent a descent into anarchy. Madison recognized that too much of a centralized authority, as seen with Britain King and Parliament, is too great of a risk for any nation. Yet, the government offered in the Articles of Confederation was far too weak on a centralized level. The fact that the Articles possessed so much fragmented and decentralized freedom was something that Madison saw as a reason why taxes could not be collected, the cost of the war could not be defrayed, and why the economic depression gripped the new nation. Shays' Rebellion, a farmer uprising led by Daniel Shays as a means of protesting the ineffectiveness of government, was something that Madison saw as an intrinsic wrong that government and society could not tolerate. It is here where Madison viewed liberty as important, but not at the cost of government ineffectiveness and the breakdown of society.
Patrick Henry presented the opposite view of this in his Anti- Federalist point of view. Henry advocated a political belief system that stressed freedom and liberty as the ultimate goal of a post- Revolutionary America. Henry argued that essentially swapping one form of centralized tyranny from Britain to America was not a deal worth having. Henry believed that liberty and individual entitlements have to be protected regardless of the cost.
For both thinkers, liberty was essential and seen as important. Yet, both saw it in different lights. The Federalist side of Madison believed that freedom had its place in a political order of structure and clarity. The Antifederalist side of Henry stressed that freedom is the ultimate end of all political expressions in the new nation. In both views of liberty, the fundamental debate of the Constitutional Convention was present and through this debate, the modern Constitution of America took form.