Editor’s Note: This article is part of “The Unfinished Revolution,” a project exploring 250 years of the American experiment.
Shays’s Rebellion filled Alexander Hamilton with dread. In 1786, armed men shut down courts in five counties across Massachusetts and, early the next year, marched on the federal armory in Springfield. The mobs included debtors trying to prevent the courts from foreclosing on their farms, and opponents of centralized government. The insurrectionists believed that the newly adopted Massachusetts Constitution, drafted in 1779 by John Adams, would shift power from the poor to the rich, from the many to the few, from the backcountry to Boston, from democracy to aristocracy. They were led by Daniel Shays, a dashing Revolutionary War veteran who’d had to sell a sword given to him by the Marquis de Lafayette to pay his debts.
Observing the rebellion from New York, Hamilton worried that civil unrest in Massachusetts could augur the rise of a demagogue on the national stage, one who might pander to angry debtors across America and threaten the stability of the new nation. The insurrection was eventually put down by a private army hired by Massachusetts Governor James Bowdoin, after members of the state militia refused his call to do so. But what might have happened, Hamilton wrote, if, instead of Shays, the rebellion “had been headed by a Caesar or by a Cromwell”?
In Hamilton’s view, the greatest threat to the American experiment was a demagogue who might flatter the people, overthrow popular elections, and consolidate power in his own hands. “Of those men who have overturned the liberties of republics,” he wrote in “Federalist No. 1,” “the greatest number have begun their career by paying an obsequious court to the people.”
Afraid that Shays’s Rebellion might spread, Hamilton and James Madison called the Constitutional Convention in 1787. George Washington agreed to attend, because he shared Hamilton and Madison’s concern that, under the Articles of Confederation, the new nation was vulnerable to men like Shays. “I could not resist the call to a convention of the States,” he wrote to Lafayette, “which is to determine whether we are to have a Government of respectability under which life, liberty, and property will be secured to us,” or one “springing perhaps from anarchy and Confusion, and dictated perhaps by some aspiring demagogue.”
[From the October 2018 issue: Jeffrey Rosen on how James Madison’s mob-rule fears have been realized]
A central goal of the convention was to check populist mobs in the states and empower the national government to defend itself. Because the undisciplined Massachusetts militia had failed to stop Shays, the new Constitution gave Congress the power to nationalize the state militias “to execute the Laws of the Union, suppress Insurrections and repel Invasions.” Hamilton would have gone even further in creating a strong central government and an energetic executive. In a notorious speech at the convention, he proposed a president elected for life who would have no temptation to resort to demagoguery to extend his term.
Thomas Jefferson was serving as the American minister in Paris when he learned of Shays’s Rebellion. His reaction differed dramatically from Hamilton’s. In Jefferson’s view, the government should be restrained in its response to popular uprisings. “The late rebellion in Massachusets has given more alarm than I think it should have done,” he wrote to Madison. “Calculate that one rebellion in 13 states in the course of 11 years, is but one for each state in a century & a half. No country should be so long without one. Nor will any degree of power in the hands of government prevent insurrections.”
Jefferson remained in Paris during the Constitutional Convention but followed its progress from abroad. “Our Convention has been too much impressed by the insurrection of Massachusets,” he wrote to John Adams’s son-in-law in 1787. “What country can preserve it’s liberties if their rulers are not warned from time to time that their people preserve the spirit of resistance? Let them take arms.”
Jefferson would have pardoned the rebels, relying on a free press to disabuse those who had participated based on misinformation. “The remedy is to set them right as to facts, pardon and pacify them. What signify a few lives lost in a century or two? The tree of liberty must be refreshed from time to time with the blood of patriots and tyrants. It is it’s natural manure.”
Jefferson felt that the presidency created by the new Constitution was too strong. He, too, feared a Caesar: His study of ancient history had convinced him that all “elective monarchies” had ended with popular leaders converting themselves into hereditary despots. But if Hamilton envisioned a demagogue who would flatter the majority from below, Jefferson foresaw one who would thwart majority will from above. He was especially concerned that an unscrupulous president might narrowly lose a bid for reelection and falsely insist that the contest had been stolen.
“He will pretend false votes, foul play, hold possession of the reins of government, be supported by the states voting for him,” Jefferson wrote to Madison. His solution was not a life term but a one-term limit for the presidency—“an incapacity to be elected a second time.”
Hamilton’s and Jefferson’s radically different responses to Shays’s Rebellion represent an opening skirmish in one of the most consequential intellectual battles among the Founders. In the Declaration of Independence, Jefferson had defined America in terms of three shining ideas: liberty, equality, and government by consent. Just a decade later, after the new Constitution was drafted, he and Hamilton began a debate about the relationship among these three ideas that has shaped American life ever since.
For Jefferson, centralized power threatened liberty; for Hamilton, a vigorous national government could help secure it. Jefferson, the author of the Declaration, was determined to expand democracy; Hamilton, the defender of the Constitution, viewed democracy as a turbulent force to be filtered and checked. Jefferson believed in local self-government and states’ sovereignty; Hamilton believed in the Union and national supremacy. Jefferson, the gentleman planter, exalted rule by the people and feared the tyranny of consolidation; Hamilton, the scholar-warrior, preferred rule by elites and dreaded the anarchy of the mob. Jefferson revered the white farmers of the agricultural South; Hamilton championed the financiers and manufacturers of the urban North. Their opposing visions led to opposing approaches to the Constitution. Jefferson interpreted it strictly, to limit federal power; Hamilton interpreted it liberally, to expand federal power.
The competing positions of Hamilton and Jefferson are like golden and silver threads woven through the tapestry of American history, sometimes running parallel to each other, sometimes crossing, and at crucial moments pulling so far apart that they threaten to snap. From the founding until today, a productive tension between the two men’s ideas has mostly kept American politics from descending into violence. Whenever the threads have been pulled too far in one direction, however, the shooting begins.
The new Constitution wasn’t yet five years old when the nation was tested again by internal violence. White farmers in Western Pennsylvania resented a new federal tax on grain, one of their main sources of revenue—and the fact that those accused of evading the tax had to stand trial in federal court in Philadelphia, far from the frontier. In July 1794, an armed mob of about 500 men attacked the federal tax collector. Like the Shaysites, the Whiskey Rebels saw themselves as a protest movement against economic inequality.
Once again, Hamilton and Jefferson reacted to the violence in radically different ways. The whiskey tax had been Hamilton’s idea. It was the centerpiece of the financial plan he’d proposed in 1790, intended to help the new federal government pay interest on debts it had assumed from the states. Hamilton recommended a military response to the rebellion, with himself at the head of an expanded army; he believed an “imposing” force was needed to “suppress the insurrection and support the Civil Authority in effectuating Obedience to the laws and the punishment of offenders.” Jefferson, by contrast, viewed the uprising as a legitimate form of civil disobedience. He saw the yeoman farmers as virtuous freedom fighters reluctantly trading their plowshares for swords.
On September 25, Washington issued a proclamation calling up the militias of Virginia, Maryland, New Jersey, and Pennsylvania. Several days later, he and Hamilton convened on Market Street in Philadelphia and decorously set off for war in a carriage. Washington inspected his troops in Carlisle and traveled with them as far as Bedford, becoming the only sitting president to command an army in the field. Then he returned to Philadelphia, leaving Hamilton in charge of a force that eventually swelled to nearly 13,000 men. Advancing west, the army found the resistance melting away. By late October, the insurrection was over.
Hamilton was confident that the successful suppression of the insurgency would ultimately strengthen the Union. Jefferson, once again, pleaded for leniency for the insurgents. Washington’s response found a middle ground. He ordered local leaders of the insurrection arrested, but absolved rank-and-file followers. Over the next year, the federal government tried a dozen men for high treason. Two men were convicted and sentenced to hang. In the end, Washington pardoned both, the first pardons to be issued by an American president.
It took the political chameleon Aaron Burr to make Hamilton and Jefferson see the other man’s perspective. Though the Whiskey Rebellion had only hardened their differences, they could agree that Burr posed a unique threat to the republic. Hamilton supported Jefferson over Burr in the 1800 election; he recognized, in Burr, a man who might become the American Caesar he’d foreseen. At a dinner in February 1804, Hamilton shared his fears that Burr would foment insurrection; an account of Hamilton calling Burr a “dangerous man” found its way into the newspapers. Burr demanded an apology. Hamilton’s refusal to apologize led him, on July 11, to the dueling grounds below the cliffs of Weehawken.
After slaying his rival, Burr vindicated Hamilton’s fears. He offered his services to the British ambassador as the leader of an insurrectionist movement that would incite the western states to secede from the Union. During Burr’s eventual trial for treason, one of his associates testified that he had also hoped to enlist the Marine Corps in a plot to seize Washington, D.C. (“Hang him!” Burr reportedly said of President Jefferson, praising dictators from ancient history, including “Caesar, Cromwell, and Bonaparte.”)
In 1806, Jefferson was sufficiently alarmed by the reports of Burr’s activities that he asked Madison what powers the president had to put down insurrections by force. Madison responded that, according to the Insurrection Act of 1792, state militias could be called to repel insurrections against the U.S., but “it does not appear that regular Troops can be employed.”
Jefferson then sought new tools. In December, he drafted “a Bill authorising the emploiment of the land or Naval forces of the US. In cases of insurrection.” He sent the bill to Congress through proxies and signed the amended Insurrection Act on March 3, 1807.
Burr was arrested for conspiracy before he could foment any kind of revolt that would require using the amended Insurrection Act. But Jefferson invoked it in 1808 to quash protests in Vermont against his Embargo Act. The Insurrection Act has served ever since as the most important legal instrument authorizing military force for domestic law enforcement. From the Civil War to the civil-rights movement, presidents have invoked it to put down violent resistance to federal authority. Having previously held that “a little rebellion now and then is a good thing,” Jefferson might not have appreciated the irony.
Insurrectionary violence has recurred throughout American history. It erupted during the secession crisis in 1861 that sparked the Civil War and the white-supremacist insurgencies across the South during Reconstruction. It reemerged in the Ku Klux Klan terror of the 1920s, and during the civil-rights era as violent opposition to racial integration, including at Little Rock in 1957 and Selma in 1965. Nearly all of these outbursts of what the historian Jefferson Cowie has called “white resistance to federal power” led presidents to invoke Jefferson’s Insurrection Act. They also used the act against a separate strain of Black resistance to state and federal power, beginning with the slave rebellion in Virginia suppressed by Andrew Jackson in 1831 through the violent protests against racism suppressed by Franklin D. Roosevelt in 1943, Lyndon B. Johnson in 1967, and George H. W. Bush in 1992.
But nothing in American history anticipated the events of January 6, 2021, when men and women stormed the U.S. Capitol at the urging of the president of the United States. They had been sold a conspiracy theory: that the 2020 election had been stolen. The leader of the Proud Boys, the far-right militia group that led the attack, invoked an apocryphal line from Thomas Jefferson to justify the insurrection: “When governments fear the people … There is liberty.”
President Donald Trump defended January 6 as a “day of love” on which there was “nothing done wrong,” and denounced the prosecution of the insurrectionists. Like Jefferson, he supported pardons rather than prosecutions. He was less interested, though, in disabusing the participants of the conspiracy theory that had motivated their actions.
On January 20, 2025, the first day of his second term, Trump pardoned or commuted the sentences of about 1,600 people involved in the January 6 attacks. He then set out to consolidate executive power, with the acquiescence of Congress. Asserting the president’s unitary control over the executive branch, he fired or bought out more than 100,000 federal workers; he also fired the heads of independent agencies and challenged the agencies’ constitutionality before the Supreme Court.
Trump’s defenders insist that his actions fall squarely within the tradition of the Hamilton-Jefferson debate. Allysia Finley, a member of The Wall Street Journal ’s editorial board, wrote in February that Hamilton would have approved of Trump’s vigorous use of executive power. Alan Dershowitz, who had defended Trump in his first impeachment trial, argued that Jefferson would have approved as well. “As soon as our third president was elected, he fired many Federalist government officials and issued blanket pardons to people the previous administration had prosecuted for sedition,” Dershowitz noted in a letter to the editor of the Journal. In Dershowitz’s view, Trump was making a legitimate effort to consolidate political power and authority in the executive branch.
Many of Trump’s supporters see him not as a Caesar but as a modern-day Andrew Jackson, resurrecting a version of Jackson’s “spoils system” to shrink the size of government and return power from the elite to the people. Trump himself has encouraged the comparison: On Jackson’s 250th birthday, he visited the Hermitage, Jackson’s Tennessee home, and likened himself to the hero of New Orleans. “It was during the Revolution that Jackson first confronted and defied an arrogant elite,” Trump said. “Oh, I know the feeling, Andrew.”
Trump’s critics, by contrast, see him as the second coming of Aaron Burr, a man who unites Hamilton’s and Jefferson’s greatest fears for American democracy: Hamilton’s demagogic Caesar and Jefferson’s oligarchic one. History suggests that they were both right about the threats to popular sovereignty; since the fall of the Greek and Roman republics, authoritarian rulers have sought to consolidate power in their own hands by flattering the mob and co-opting the financial elite.
Throughout American history, followers of Hamilton and Jefferson have warned that when Americans abandon their devotion to the principles of the Constitution, political conflict ends in tyranny, violence, or both. The warnings have taken the form of what the Puritan scholar Sacvan Bercovitch called the “American Jeremiad.” Just as Puritan political sermons warned that Americans, like the ancient Israelites, had lost their way by violating their covenant with God, so Revolutionary-era jeremiads warned that Americans, like the citizens of ancient Rome, risked losing their way by abandoning their devotion to liberty, civic virtue, the rule of law, and the principles of the Constitution. In 1772, three years before he was killed at the Battle of Bunker Hill, the Patriot Joseph Warren wrapped himself in a toga and cautioned that the Romans’ spurning of their “noble attachment to a free constitution” had enabled Caesar to consolidate absolute power. He urged Americans not to do the same.
The success of the American experiment doesn’t require agreement between Hamiltonians and Jeffersonians about how to balance liberty and power; it requires a good-faith commitment to participate in the inevitable tug-of-war between them. In his final years, Jefferson placed a bust of Hamilton in the front hall of Monticello, facing his own bust. He viewed his greatest foe not as a hated enemy to be destroyed but as a respected opponent to be defeated, and he accepted his own defeats as an opportunity to fight another day. During the two decades that he survived Hamilton, Jefferson would remark to visitors that the two men remained “opposed in death as in life,” sometimes emphasizing the point with a smile. The two busts remain on opposite sides of the main entrance at Monticello today, an enduring sign of Jefferson’s respect, if not affection, for his most significant foe.
This article was adapted from Jeffrey Rosen’s new book, The Pursuit of Liberty: How Hamilton vs. Jefferson Ignited the Lasting Battle Over Power in America. It appears in the November 2025 print edition with the headline “The Nightmare of Despotism.”
