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Hamilton, Jefferson, and how best to preserve freedom
Hamilton, Jefferson, and how best to preserve freedom
Oct 14, 2026 4:14 PM

Despite both being deeply dedicated to protecting Americans from tyranny, Alexander Hamilton and Thomas Jefferson disagreed on a great deal. In a new review of Hamilton versus Jefferson in the Washington Administration: Completing the Founding or Betraying the Founding, Samuel Gregg calls the founders’ rivalry, “stark, but intricate.” Gregg discusses Carson Holloway’s new book in a recent article for the Library of Law and Liberty. It’s easy to idolize the founders, but Gregg reminds us that they were “given to occasional pettiness. They lost their tempers. They often resorted to underhanded methods to get their way. Nor were they above scheming against each other.”

Alexander Hamilton and Thomas Jefferson disagreed about the new Constitution and its role in governing the new United States. Holloway’s book and Gregg’s review focus on this significant disagreement.

Gregg summarizes the book:

Holloway approaches the conflict between the Virginia planter and the self-made dynamo from the Caribbean in three parts. Beginning with their debates about the most optimal way of arranging the federal government’s finances and thus setting the nation’s general economic direction, Holloway then studies their deeper rupture over the powers of the executive branch before turning to their battles over foreign policy, at which point he brings the Pacificus–Helvidiusdebates between Hamilton and James Madison into the discussion.

One of the achievements of this book is the way it takes us inside the philosophical framework that informed the back-and-forth between Hamilton and Jefferson as the two struggled for intellectual ascendancy within the administration. Neither of them regarded the Constitution as existing in a theoretical vacuum. Both referenced, as Holloway demonstrates, a variety of classical, medieval, and early modern authorities as they debated the meaning and implications of different articles and clauses of the Constitution. Christian Wolff, Baron de Montesquieu, and the jurists Emer de Vattel and Samuel von Pufendorf are mentioned frequently in these memoranda, alongside terms such as “the law of nature,” “natural law,” “natural rights,” and “the law of nations.”

A crucial difference between the two men emphasized by Holloway is Hamilton’s willingness to invoke general appeals to “the ‘practice of mankind’”—that is, to the habits of the established European powers—which he held “ought to have great weight against the theories of individuals.” This matters because it underscores that Hamilton’s focus was upon building the United States as a nation of free men as well as his willingness to read the Constitution through that lens. Conversely, Jefferson prioritized the preservation of liberty from excessively powerful government. It was the restraining of government, Jefferson believed, that would set this republic apart from the other regimes of the time. For Hamilton, however, the preservation of liberty, whether against foreign threats or the internal menace of anarchy, meant that the United States had to acquire the capacities possessed by other strong sovereign states.

What is the ultimate purpose of this book for the contemporary reader?

[T]o present the Hamilton-Jefferson debate as a way of illustrating how Americans can disagree about many policy questions and yet do so in a way that reflects a mitment to living in accord with established constitutional and moral principles. “To say the founding can offer us no easy lessons in these disputes,” Holloway states, “is not to say that it can offer us no positive lessons at all.” Hamilton and Jefferson quarreled frequently about how to understand particular constitutional articles and the legitimacy of specific proposals for action. Yet the fundamental constitutional principles “were never far from their minds, or absent from their arguments” as they grappled plicated domestic and foreign policy conundrums.

Read Samuel Gregg’s full review at the Library of Law and Liberty.

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