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Tag: Alexander Hamilton

The Fatal Meeting: When Hamilton and Burr Settled Fifteen Years of Rivalry with Pistols

The story of the Hamilton-Burr duel has all the elements of a Greek tragedy: brilliant men, political ambition, an unforgiving honor culture, and an ending that destroyed both victor and vanquished alike. When Aaron Burr shot Alexander Hamilton on the morning of July 11, 1804, he didn’t just kill one of America’s founding architects—he also ended his own political career and helped doom the entire Federalist Party to irrelevance. Let’s rewind the clock more than a decade to try and understand how these two gifted lawyers and Revolutionary War veterans ended up facing each other with loaded pistols.

The Long Road to Weehawken

Hamilton and Burr moved in the same elite New York political circles from the 1790s onward, but they had remarkably different temperaments and political beliefs. Hamilton was ideological, prolific, and combative—often too much so for his own good. Burr was pragmatic, opaque, self-serving, and famously hard to pin down on principle. They distrusted each other deeply.

Their rivalry stretched back to 1791, when Burr defeated Philip Schuyler for a U.S. Senate seat representing New York. This wasn’t just any political defeat for Hamilton—Schuyler was his father-in-law and a crucial Federalist ally on whom Hamilton had counted to support his ambitious financial programs. Hamilton, who was serving in George Washington’s cabinet as Treasury Secretary, never forgave Burr for this loss. In correspondence from June 1804, Hamilton himself referenced “a course of fifteen years competition” between the two men.  

Their philosophical differences ran deep. Hamilton was an ideological Federalist who dreamed of transforming the United States into a modern economic power rivaling European empires through strong central government, industrial development, and military strength. Burr, by contrast, approached politics more pragmatically—he saw it as a vehicle for advancing his own interests and those of his allies rather than as a way to implement sweeping political visions. As Burr himself allegedly said, politics were nothing more than “fun and honor and profit”. Hamilton viewed Burr as fundamentally dangerous due to his lack of fixed ideological principles. Hamilton wrote in 1792 that he considered it his “religious duty to keep this man from office”

The election of 1800 brought their animosity to a boiling point. Due to a quirk in the original Constitution’s electoral system, Thomas Jefferson and his running mate Aaron Burr tied in the Electoral College with 73 votes each, allowing the Federalists to briefly consider elevating Burr to the presidency.  The decision went to the House of Representatives, and Hamilton—despite despising Jefferson’s Democratic-Republican politics—campaigned hard to ensure Jefferson won the presidency rather than Burr. Hamilton argued that Jefferson, however wrong in policy, had convictions, whereas Burr had none.  In the end, Jefferson gained the presidency and Burr became Vice President, but their relationship was never collegial and Burr was excluded from any meaningful participation in Jefferson’s administration.

By 1804, it was clear Jefferson would not consider Burr for a second term as Vice President. Desperate to salvage his political career, Burr made a surprising move: he sought the Federalist nomination for governor of New York, switching from his Democratic-Republican affiliation. It was a strange gambit—essentially betting that his political enemies might support him if it served their interests. Hamilton, predictably, worked vigorously to block Burr’s ambitions yet again. Although Hamilton’s opposition wasn’t the only factor, Burr lost badly to Morgan Lewis, the Democratic-Republican candidate, in April 1804.

The Cooper Letter and the Challenge

The immediate trigger for the duel came from a relatively minor slight in the context of their long feud. In February 1804, Dr. Charles Cooper attended a dinner party where Hamilton spoke forcefully against Burr’s candidacy. Cooper later wrote to Philip Schuyler describing Hamilton’s comments, noting that Hamilton had called Burr “a dangerous man” and referenced an even “more despicable opinion” of him. This letter was published in the Albany Register in April, after Burr’s electoral defeat.

When the newspaper reached Burr, he was already politically ruined—still Vice President of the United States, but with no prospects for future office. He demanded that Hamilton acknowledge or deny the statements attributed to him. What followed was a formal exchange of letters between the two men and their representatives that lasted through June. Hamilton refused to give Burr the straightforward denial he sought, explaining that he couldn’t reasonably be expected to account for everything he might have said about a political opponent during fifteen years of competition. Burr, seeing his honor impugned and his options exhausted, invoked the code of honor and issued a formal challenge to duel.

Hamilton found himself in an impossible position. If he admitted to the insults, which were substantially true, he would lose his honor. If he refused to duel, the result would be the same—his political career would effectively end. Hamilton had personal and moral objections to dueling. His eldest son Philip had died in a duel just three years earlier, at the same Weehawken location where Hamilton and Burr would meet. Hamilton calculated that his ability to maintain his political influence required him to conform to the codes of honor that governed gentlemen’s behavior in early America.

Dawn at Weehawken

At 5:00 AM on the morning of July 11, 1804, the men departed Manhattan from separate docks. They were each rowed across the Hudson River to the Heights of Weehawken, New Jersey—a popular dueling ground where at least 18 known duels took place between 1700 and 1845. They chose New Jersey because while dueling had been outlawed in both New York and New Jersey, the New Jersey penalties were less severe.

Burr arrived first around 6:30 AM, with Hamilton landing about thirty minutes later. Each man was accompanied by his “second”—an assistant responsible for ensuring the duel followed proper protocols. Hamilton brought Nathaniel Pendleton, a Revolutionary War veteran and Georgia district court judge, while Burr’s second was William Van Ness, a New York federal judge. Hamilton also brought Dr. David Hosack, a Columbia College professor of medicine and botany, in case medical attention proved necessary.

Shortly after 7 a.m., the seconds measured out ten paces, loaded the .56‑caliber pistols, and explained the firing rules before Hamilton and Burr took their positions. What exactly happened next remains one of history’s enduring mysteries. The seconds gave conflicting accounts, and historians still debate the sequence and meaning of events.

In a written statement before the duel, Hamilton expressed religious and moral objections to dueling, worry for his family and creditors, and professed no personal hatred of Burr, yet concluded that honor and future public usefulness compelled him to accept. By some accounts, Hamilton had also written to confidants indicating his intention to “throw away my shot”—essentially to deliberately miss Burr, satisfying the requirements of honor without attempting to kill his opponent. Burr, by contrast, appears to have aimed directly at Hamilton.

Some accounts suggest Hamilton fired first, with his shot hitting a tree branch above and behind Burr’s head. Other versions claim Burr shot first. There’s even a theory that Hamilton’s pistol had a hair trigger that caused an accidental discharge after Burr wounded him.

What’s undisputed is the outcome: Burr’s shot struck Hamilton in the lower abdomen, with the bullet lodging near his spine. Hamilton fell, and Burr reportedly started toward his fallen opponent before Van Ness held him back, worried about the legal consequences of lingering at the scene. The two parties crossed back to Manhattan in their respective boats, with Hamilton taken to the home of William Bayard Jr. in what is now Greenwich Village.

Hamilton survived long enough to say goodbye to his wife Eliza and their children. He died at 2 PM on July 12, 1804, approximately 31 hours after being shot.

Political Aftershocks

The nation was outraged. While duels were relatively common in early America, they rarely resulted in death, and the killing of someone as prominent as Alexander Hamilton sparked widespread condemnation. The political consequences proved catastrophic for everyone involved—and reshaped American politics for the next two decades.

Hamilton’s death turned him into a Federalist martyr. Even many who had disliked his arrogance now praised his intellect, service, and sacrifice. His economic vision, already embedded in American institutions, gained a kind of posthumous authority.

For Aaron Burr, the duel destroyed him politically and socially. Murder charges were filed against him in both New York and New Jersey, though neither reached trial—a grand jury in Bergen County, New Jersey indicted him for murder in November 1804, but the New Jersey Supreme Court quashed the indictment. Nevertheless, Burr fled to St. Simons Island, Georgia, staying at the plantation of Pierce Butler, before returning to Washington to complete his term as Vice President.

Rather than restoring his reputation as he’d hoped, the duel made Burr a pariah. He would never hold elected office again. His subsequent attempt to regain power through what historians call the “Burr Conspiracy”—an alleged plan to create an independent nation along the Mississippi River by separating territories from the United States and Spain—led to a treason trial in 1807. Chief Justice John Marshall presided and Burr was ultimately acquitted, but the trial further cemented Burr’s reputation as a dangerous schemer. He spent his later years quietly practicing law in New York.

For the Federalist Party, Hamilton’s death proved even more devastating than Burr’s personal ruin. Hamilton had been the party’s intellectual architect and most effective leader. At the time of his death, the Federalists were attempting a comeback after their national defeat in the 1800 election. Without Hamilton’s energy, strategic thinking, and ability to articulate a compelling vision for the country, the Federalists lost direction. As one historian put it, “The Federalists would be unable to find another leader as forceful and energetic as Hamilton had been, and their movement would slowly suffocate before finally petering out in the early 1820s”. The party’s decline ended what historians consider the first round of partisan struggles in American history.

An interesting footnote: while many Federalists wanted to portray Hamilton as a political martyr, Federalist clergy broke with the party line to condemn dueling itself as a violation of the sixth commandment. These ministers used Hamilton’s death as an opportunity to wage a moral crusade against the practice of dueling, helping to accelerate its decline in American culture—particularly in the northern states where it was already losing favor.

The duel produced a triple tragedy: Hamilton dead at age 47 (or 49—his birth year remains disputed), Burr politically destroyed despite being acquitted of murder charges, and the Federalist Party fatally weakened at a critical moment in American political development.

The Hamilton–Burr duel sits at the intersection of politics, personality, and culture. It reminds us that the early republic was not a calm, rational experiment run by marble statues—but a volatile environment shaped by ego, fear, and ambition. Institutions were young, norms were fragile, and reputations were all important. What began as fifteen years of professional rivalry and personal enmity ended with two brilliant men eliminating each other from the political stage, neither achieving what they’d hoped for through their fatal meeting on the heights of Weehawken.

Sources

Encyclopedia Britannica “Burr-Hamilton duel | Summary, Background, & Facts” https://www.britannica.com/event/Burr-Hamilton-duel

History.com “Aaron Burr slays Alexander Hamilton in duel” https://www.history.com/this-day-in-history/july-11/burr-slays-hamilton-in-duel

Library of Congress “Today in History – July 11” https://www.loc.gov/item/today-in-history/july-11

National Constitution Center “The Burr vs. Hamilton duel happened on this day” https://constitutioncenter.org/blog/burr-vs-hamilton-behind-the-ultimate-political-feud

National Park Service “Hamilton-Burr Duel” https://www.nps.gov/articles/000/hamilton-burr-duel.htm

PBS American Experience “Alexander Hamilton and Aaron Burr’s Duel” https://www.pbs.org/wgbh/americanexperience/features/duel-alexander-hamilton-and-aaron-burrs-duel/

The Gospel Coalition “American Prophets: Federalist Clergy’s Response to the Hamilton–Burr Duel of 1804” https://www.thegospelcoalition.org/themelios/article/american-prophets-federalist-clergys-response-to-the-hamilton-burr-duel-of-1804/

Wikipedia “Burr–Hamilton duel” https://en.wikipedia.org/wiki/Burr–Hamilton_duel

World History Encyclopedia “Hamilton-Burr Duel” https://www.worldhistory.org/article/2548/hamilton-burr-duel/​​​​​​​​​​​​​​​​

For more information about the history of dueling in early America see my earlier post: Pistols at Dawn, The Rise and Fall of the Code Duello.

Images generated by author using ChatGPT.

The Founding Feuds: When America’s Heroes Couldn’t Stand Each Other

The mythology of the founding fathers often portrays them as a harmonious band of brothers united in noble purpose. The reality was far messier—these brilliant, ambitious men engaged in bitter personal feuds that sometimes threatened the very republic they were creating.  In some ways, the American revolution was as much of a battle of egos as it was a war between King and colonists.

The Revolutionary War Years: Hancock, Adams, and Washington’s Critics

The tensions began even before independence was declared. John Hancock and Samuel Adams, both Massachusetts firebrands, developed a rivalry that simmered throughout the Revolution. Adams, the older political strategist, had been the dominant figure in Boston’s resistance movement. When Hancock—wealthy, vain, and eager for glory—was elected president of the Continental Congress in 1775, the austere Adams felt his protégé had grown too big for his britches. Hancock’s request for a leave of absence from the presidency of Congress in 1777 coupled with his desire for an honorific military escort home, struck Adams as a relapse into vanity. Adams even opposed a resolution of thanks for Hancock’s service, signaling open estrangement. Their relationship continued to deteriorate to the point where they barely spoke, with Adams privately mocking Hancock’s pretensions and Hancock using his position to undercut Adams politically.

The choice of Washington as commander sparked its own controversies. John Adams had nominated Washington, partly to unite the colonies by giving Virginia the top military role. Washington’s command was anything but universally admired and as the war dragged on with mixed results many critics emerged.

After the victory at Saratoga in 1777, General Horatio Gates became the focal point of what’s known as the Conway Cabal—a loose conspiracy aimed at having Gates replace Washington as commander-in-chief. General Thomas Conway wrote disparaging letters about Washington’s military abilities. Some members of Congress, including Samuel Adams, Thomas Mifflin, and Richard Henry Lee, questioned whether Washington’s defensive strategy was too cautious and if his battlefield performance was lacking. Gates himself played a duplicitous game, publicly supporting Washington while privately positioning himself as an alternative.

When Washington discovered the intrigue, his response was characteristically measured but firm.  Rather than lobbying Congress or forming a counter-faction, Washington leaned heavily on reputation and restraint. He continued to communicate respectfully with Congress, emphasizing the army’s needs rather than defending his own position.  Washington did not respond with denunciations or public accusations. Instead, he handled the situation largely behind the scenes. When he learned that Conway had written a critical letter praising Gates, Washington calmly informed him that he was aware of the letter—quoting it verbatim.

The conspiracy collapsed, in part because Washington’s personal reputation with the rank and file and with key political figures proved more resilient than his critics had anticipated. But the episode exposed deep fractures over strategy, leadership, and regional loyalties within the revolutionary coalition.

The Ideological Split: Hamilton vs. Jefferson and Madison

Perhaps the most consequential feud emerged in the 1790s between Alexander Hamilton and Thomas Jefferson, with James Madison eventually siding with Jefferson. This wasn’t just personal animosity—it represented a fundamental disagreement about America’s future.

Hamilton, Washington’s Treasury Secretary, envisioned an industrialized commercial nation with a strong central government, a national bank, and close ties to Britain. Jefferson, the Secretary of State, championed an agrarian republic of small farmers with minimal federal power and friendship with Revolutionary France. Their cabinet meetings became so contentious that Washington had to mediate. Hamilton accused Jefferson of being a dangerous radical who would destroy public credit. Jefferson called Hamilton a monarchist who wanted to recreate British aristocracy in America.

The conflict got personal. Hamilton leaked damaging information about Jefferson to friendly newspapers. Jefferson secretly funded a journalist, James Callender, to attack Hamilton in print. When Hamilton’s extramarital affair with Maria Reynolds became public in 1797, Jefferson’s allies savored every detail. The feud split the nation into the first political parties: Hamilton’s Federalists and Jefferson’s Democratic-Republicans. Madison, once Hamilton’s ally in promoting the Constitution, switched sides completely, becoming Jefferson’s closest political partner and Hamilton’s implacable foe.

The Adams-Jefferson Friendship, Rivalry, and Reconciliation

John Adams and Thomas Jefferson experienced one of history’s most remarkable personal relationships. They were close friends during the Revolution, working together in Congress and on the committee to draft the Declaration of Independence (though Jefferson did the actual writing). Both served diplomatic posts in Europe and developed deep mutual respect.

But the election of 1796 turned them into rivals. Adams won the presidency with Jefferson finishing second, making Jefferson vice president under the original constitutional system—imagine your closest competitor becoming your deputy. By the 1800 election, they were bitter enemies. The campaign was vicious, with Jefferson’s supporters calling Adams a “hideous hermaphroditical character” and Adams’s allies claiming Jefferson was an atheist who would destroy Christianity.

Jefferson won in 1800, and the two men didn’t speak for over a decade. Their relationship was so bitter that Adams left Washington early in the morning, before Jefferson’s inauguration. What makes their story extraordinary is the reconciliation. In 1812, mutual friends convinced them to resume correspondence. Their letters over the next fourteen years—158 of them—became one of the great intellectual exchanges in American history, discussing philosophy, politics, and their memories of the Revolution. Both men died on July 4, 1826, the fiftieth anniversary of the Declaration of Independence, with Adams’s last words reportedly being “Thomas Jefferson survives” (though Jefferson had actually died hours earlier).

Franklin vs. Adams: A Clash of Styles

In Paris, the relationship between Benjamin Franklin and John Adams was a tense blend of grudging professional reliance and deep personal irritation, rooted in radically different diplomatic styles and temperaments. Franklin, already a celebrated figure at Versailles, cultivated French support through charm, sociability, and patient maneuvering in salons and at court, a method that infuriated Adams. He equated such “nuances” with evasiveness and preferred direct argument, formal memorandums, and hard‑edged ultimatums. Sharing lodgings outside Paris only intensified Adams’s resentment as he watched Franklin rise late, receive endless visitors, and seemingly mix pleasure with business, leading Adams to complain that nothing would ever get done unless he did it himself, while Franklin privately judged Adams “always an honest man, often a wise one, but sometimes and in some things, absolutely out of his senses.” Their French ally, Foreign Minister Vergennes, reinforced the imbalance by insisting on dealing primarily with Franklin and effectively sidelining Adams in formal diplomacy. This deepened Adams’s sense that Franklin was both overindulged by the French and insufficiently assertive on America’s behalf. Yet despite their mutual loss of respect, the two ultimately cooperated—often uneasily—in the peace negotiations with Britain, and both signatures appear on the 1783 Treaty of Paris, a testament to the way personal feud and shared national purpose coexisted within the American diplomatic mission.

Hamilton and Burr: From Political Rivalry to Fatal Duel

The Hamilton-Burr feud ended in the most dramatic way possible: a duel at Weehawken, New Jersey, on July 11, 1804, where Hamilton was mortally wounded and Burr destroyed his own political career.

Their rivalry had been building for years. Both were New York lawyers and politicians, but Hamilton consistently blocked Burr’s ambitions. When Burr ran for governor of New York in 1804, Hamilton campaigned against him with particular venom, calling Burr dangerous and untrustworthy at a dinner party. When Burr read accounts of Hamilton’s remarks in a newspaper, he demanded an apology. Hamilton refused to apologize or deny the comments, leading to the duel challenge.

What made this especially tragic was that Hamilton’s oldest son, Philip, had been killed in a duel three years earlier defending his father’s honor. Hamilton reportedly planned to withhold his fire, but he either intentionally shot into the air or missed. Burr’s shot struck Hamilton in the abdomen, and he died the next day. Burr was charged with murder in both New York and New Jersey and fled to the South.  Though he later returned to complete his term as vice president, his political career was finished.

Adams vs. Hamilton: The Federalist Crack-Up

One of the most destructive feuds happened within the same party. John Adams and Alexander Hamilton were both Federalists, but their relationship became poisonous during Adams’s presidency (1797-1801).

Hamilton, though not in government, tried to control Adams’s cabinet from behind the scenes. When Adams pursued peace negotiations with France (the “Quasi-War” with France was raging), Hamilton wanted war. Adams discovered that several of his cabinet members were more loyal to Hamilton than to him and fired them. In the 1800 election, Hamilton wrote a fifty-four-page pamphlet attacking Adams’s character and fitness for office—extraordinary since they were in the same party. The pamphlet was meant for limited circulation among Federalist leaders, but Jefferson’s allies got hold of it and published it widely, devastating both Adams’s re-election chances and Hamilton’s reputation. The feud helped Jefferson win and essentially destroyed the Federalist Party.

Washington and Jefferson: The Unacknowledged Tension

While Washington and Jefferson never had an open feud, their relationship cooled significantly during Washington’s presidency. Jefferson, as Secretary of State, increasingly opposed the administration’s policies, particularly Hamilton’s financial program. When Washington supported the Jay Treaty with Britain in 1795—which Jefferson saw as a betrayal of France and Republican principles—Jefferson became convinced Washington had fallen under Hamilton’s spell.

Jefferson resigned from the cabinet in 1793, partly from policy disagreements but also from discomfort with what he saw as Washington’s monarchical tendencies (the formal receptions and the ceremonial aspects of the presidency). Washington, in turn, came to view Jefferson as disloyal, especially when he learned Jefferson had been secretly funding attacks on the administration in opposition newspapers and had even put a leading critic on the federal payroll. By the time Washington delivered his Farewell Address in 1796, warning against political parties and foreign entanglements, many saw it as a rebuke of Jefferson’s philosophy. They maintained outward courtesy, but their warm relationship never recovered.

Why These Feuds Mattered

These weren’t just personal squabbles—they shaped American democracy in profound ways. The Hamilton-Jefferson rivalry created our two-party system (despite Washington’s warnings). The Adams-Hamilton split showed that parties could fracture from within. The Adams-Jefferson reconciliation demonstrated that political enemies could find common ground after leaving power.

The founding fathers were human, with all the ambition, pride, jealousy, and pettiness that entails. They fought over power, principles, and personal slights. What’s remarkable isn’t that they agreed on everything—they clearly didn’t—but that despite their bitter divisions, they created a system robust enough to survive their feuds. The Constitution itself, with its checks and balances, almost seems designed to accommodate such disagreements, ensuring that no single person or faction could dominate.

SOURCES

  1. National Archives – Founders Online

https://founders.archives.gov

2.   Massachusetts Historical Society – Adams-Jefferson Letters

https://www.masshist.org/publications/adams-jefferson

       3.    Founders Online – Hamilton’s Letter Concerning John Adams

https://founders.archives.gov/documents/Hamilton/01-25-02-0110

       4.    Gilder Lehrman Institute – Hamilton and Jefferson

https://www.gilderlehrman.org/history-resources/spotlight-primary-source/alexander-hamilton-and-thomas-jefferson

       5.    National Park Service – The Conway Cabal

https://www.nps.gov/articles/000/the-conway-cabal.htm

       6.    American Battlefield Trust – Hamilton-Burr Duel

https://www.battlefields.org/learn/articles/hamilton-burr-duel

        7.   Mount Vernon – Thomas Jefferson

https://www.mountvernon.org/library/digitalhistory/digital-encyclopedia/article/thomas-jefferson

        8.   Monticello – Thomas Jefferson Encyclopedia

https://www.monticello.org/research-education/thomas-jefferson-encyclopedia

        9.   Library of Congress – John Adams Papers

https://www.loc.gov/collections/john-adams-papers

10. Joseph Ellis – “Founding Brothers: The Revolutionary Generation”

https://www.pulitzer.org/winners/joseph-j-ellis

Illustration generated by author using ChatGPT.

Thomas Jefferson: The Philosopher Who Played Hardball

Here’s the thing about Thomas Jefferson that doesn’t always make it into the history textbooks: the guy who wrote those soaring words about liberty and limited government? He was also one of early America’s most skilled—and sometimes underhanded—political operators.

It’s surprising when you think about it. Jefferson genuinely believed in transparency, virtue in public life, and keeping government small. He wrote beautifully about these ideals. But when it came to actual politics? He played the game as hard as anyone, often using tactics that directly contradicted what he preached.

Jefferson’s public philosophy was straightforward. He thought America should be a nation of independent farmers—regular people who owned their own land and weren’t dependent on anyone else. He worried constantly about concentrated power, whether in government or in the hands of wealthy financiers or merchants. He believed people should be informed and engaged, and that government worked best when it stayed out of people’s lives.

His Declaration of Independence wasn’t just pretty rhetoric—it laid out a genuinely revolutionary idea: governments only have power because people agree to give it to them, and when governments stop serving the people, those people have the right to change things.

The Reality: How Jefferson Actually Operated

Here’s where it gets interesting. While Jefferson was writing about virtue and transparency, he was simultaneously running what today we’d recognize as opposition research, planting stories in the press, and organizing political operations—sometimes against people he was supposed to be working with.

The Freneau Setup: Paying for Attacks

The most blatant example happened in 1791. Jefferson was serving as Secretary of State under George Washington, which meant he was part of the administration. At the same time, he arranged for a guy named Philip Freneau to get a government job—technically as a translator. The real purpose? To give Freneau money to run a newspaper that would relentlessly attack Alexander Hamilton and other Federalists.

Think about that for a second. Jefferson was using his government position to fund media attacks on his own colleagues. When people called him out on it, he basically said, “Who, me? I have nothing to do with what Freneau publishes.” But the evidence shows Jefferson was actively encouraging and directing these attacks.

John Beckley: The Original Campaign Fixer

Jefferson also worked closely with John Beckley, who was essentially America’s first professional political operative. Beckley coordinated messaging, spread information (and sometimes misinformation) about opponents, and helped build the grassroots organization that would eventually become the Democratic-Republican Party.

This wasn’t a gentlemanly debate about ideas. This was organized political warfare—pamphlets, coordinated newspaper campaigns, and opposition research. Jefferson and Jame Madison quietly funded much of this work while maintaining public images as above-the-fray philosophers. We can’t know exactly what Jefferson said in every private conversation with Beckley, but the circumstantial evidence of coordination is convincing.

The Hamilton Rivalry: Ideological War

Jefferson’s conflict with Hamilton was both philosophical and deeply personal. Hamilton wanted a strong federal government, a national bank, and close ties with Britain. Jefferson saw all of this as a betrayal of the Revolution—a step toward creating the same kind of corrupt, elite-dominated system they’d just fought to escape.

But rather than just making his arguments publicly, Jefferson worked behind the scenes to undermine Hamilton’s policies. He encouraged Madison to lead opposition in Congress. He fed stories to friendly newspapers. He coordinated with Republican representatives to block Federalist initiatives.

The philosophical disagreement was real, but Jefferson’s methods were pure political calculation.

Turning on Washington: The Ultimate Betrayal?

Maybe the most damaging thing Jefferson did was secretly working against George Washington while still serving in his cabinet. By Washington’s second term, Jefferson had convinced himself that Washington was being manipulated by Hamilton and moving the country toward monarchy.

 Jefferson stayed in the cabinet, maintaining cordial relations with Washington in person, while privately organizing resistance to administration policies. He encouraged attacks on Washington in the press. He coordinated with opposition leaders. And he did all of this while Washington trusted him as a loyal advisor.

When Washington found out, he was devastated. The betrayal broke their relationship permanently.

The Burr Situation: Using People

Jefferson’s handling of Aaron Burr shows just how pragmatic he could be. Jefferson never really trusted Burr—thought he was too ambitious and unprincipled. But in 1800, when Jefferson needed to win the presidency, Burr was useful for delivering New York’s votes.

After winning, Jefferson kept Burr as vice president but froze him out of any real power. Once Burr’s usefulness ended (especially after he killed Hamilton in that duel), Jefferson completely abandoned him, eventually supporting an unsuccessful prosecution for treason.

Deceiving Congress

Another example of Jefferson’s political manipulation was the Louisiana Purchase. This was a massive land acquisition that doubled the size of the United States. Jefferson knew that under the constitution he had no clear authority to acquire territory for the United States.  He was able to secure the purchase by keeping it secret from both congress and his political opponents until after it was finalized. This allowed him to avoid a debate that could have derailed the deal.  Does this sound familiar?

So, What Do We Make of This?

Here’s the uncomfortable question: Was Jefferson a hypocrite, or was he just being realistic about how politics actually works?  Jefferson’s political manipulation was not always ethical, but it was effective. He was able to use his skills to achieve many of his political goals.

You could argue he was doing what he thought necessary to prevent Hamilton’s vision from taking over—that the ends justified the means. You could also argue that by using underhanded tactics, he corrupted the very democratic processes he claimed to be protecting.

My speculation: I think Jefferson was aware of the contradiction and wrestled with it. His private letters show moments of self-justification and lingering doubt. But ultimately, he kept doing it because he believed his vision for America was too important to lose by playing nice.

The Bottom Line

Thomas Jefferson remains one of our most brilliant political thinkers. But he was also willing to play dirty when he thought the stakes were high enough. That duality—beautiful ideals combined with hardball tactics—might actually make him more relevant today than ever. Because let’s be honest, that tension between principles and pragmatism hasn’t gone away in American politics.

Understanding both sides of Jefferson helps us see that even the founders we most revere weren’t simple heroes. They were complicated people operating in a messy political reality, trying to build something new while fighting over what that something should be.

The evidence for Jefferson’s political maneuvering is extensive and well-established by historians. Some interpretations of his motivations involve educated speculation, but the actions themselves are documented in letters, newspaper archives, and contemporary accounts.​​​​​​​​​​​​​​​​

Reference List

Primary Sources

Founders Online – National Archives https://founders.archives.gov/

  • Digital collection of correspondence and papers from George Washington, Thomas Jefferson, Alexander Hamilton, Benjamin Franklin, John Adams, and James Madison. Essential for Jefferson’s own words and contemporaneous accounts of his political activities.

Library of Congress – Thomas Jefferson Exhibition https://www.loc.gov/exhibits/jefferson/

  • Comprehensive digital exhibition covering Jefferson’s life, philosophy, and political career with original documents and interpretive essays.

Thomas Jefferson Encyclopedia – Monticello https://www.monticello.org/site/research-and-collections/

  • Scholarly resource maintained by the Thomas Jefferson Foundation, covering specific topics including Jefferson’s relationships with Aaron Burr and other political figures.

Secondary Sources – Books

Chernow, Ron. Alexander Hamilton. New York: Penguin Press, 2004.

  • Pulitzer Prize-winning biography that extensively covers the Jefferson-Hamilton rivalry and Jefferson’s behind-the-scenes political maneuvering, including the Freneau affair. Particularly strong on the 1790s conflicts within Washington’s cabinet.

Chernow, Ron. Washington: A Life. New York: Penguin Press, 2010.

  • Provides Washington’s perspective on Jefferson’s activities within his administration and the betrayal Washington felt when learning of Jefferson’s covert opposition.

Ellis, Joseph J. American Sphinx: The Character of Thomas Jefferson. New York: Alfred A. Knopf, 1996.

  • National Book Award winner that explores Jefferson’s contradictions and complexities, particularly the gap between his philosophical writings and political practices.

Ferling, John. Jefferson and Hamilton: The Rivalry That Forged a Nation. New York: Bloomsbury Press, 2013.

  • Detailed examination of the ideological and personal conflict between Jefferson and Hamilton, showing how their struggle shaped early American politics and party formation.

Isenberg, Nancy. Fallen Founder: The Life of Aaron Burr. New York: Penguin Books, 2007.

  • Comprehensive biography of Burr that includes extensive coverage of his complex relationship with Jefferson, from their 1800 alliance through Jefferson’s eventual abandonment of his vice president.

Pasley, Jeffrey L. The Tyranny of Printers: Newspaper Politics in the Early American Republic. Charlottesville: University of Virginia Press, 2001.

  • Scholarly examination of how newspapers and partisan press became political weapons in the 1790s, with detailed coverage of Jefferson’s relationship with Philip Freneau and the National Gazette.

Secondary Sources – Journal Articles and Academic Papers

Sharp, James Roger. “The Journalist as Partisan: The National Gazette and the Origins of the First Party System.” The Virginia Magazine of History and Biography 97, no. 4 (1989): 391-420.

  • Academic analysis of Freneau’s National Gazette and its role in forming political opposition, including Jefferson’s involvement in funding and directing the publication.

Cunningham, Noble E., Jr. “John Beckley: An Early American Party Manager.” The William and Mary Quarterly 13, no. 1 (1956): 40-52.

  • Scholarly examination of Beckley’s role as America’s first professional political operative and his work organizing Jefferson’s political machine.

Historiographical Note

The interpretation of Jefferson’s political behavior has evolved over time. Earlier biographies (pre-1960s) tended to minimize or excuse his behind-the-scenes maneuvering, while more recent scholarship has been willing to examine the contradictions between his philosophy and practice more critically. The works cited above represent current historical consensus based on documentary evidence, though historians continue to debate Jefferson’s motivations and whether his tactics were justified given the political stakes he perceived.

Hamilton And Lincoln Still Have Something To Tell US

Objections and Answers respecting the Administration
of the Government

Alexander Hamilton 18 August 1792

“The truth unquestionably is, that the only path to a subversion of the republican system of the Country is, by flattering the prejudices of the people, and exciting their jealousies and apprehensions, to throw affairs into confusion, and bring on civil commotion…

When a man unprincipled in private life, desperate in his fortune, bold in his temper, possessed of considerable talents, having the advantage of military habits—despotic in his ordinary demeanour—known to have scoffed in private at the principles of liberty—when such a man is seen to mount the hobby horse of popularity—to join in the cry of danger to liberty—to take every opportunity of embarrassing the General Government & bringing it under suspicion—to flatter and fall in with all the non sense of the zealots of the day—It may justly be suspected that his object is to throw things into confusion that he may “ride the storm and direct the whirlwind.””

Speech to the Young Men’s Lyceum of Springfield

Abraham Lincoln 1838

   Is it unreasonable then to expect, that some man possessed of the loftiest genius, coupled with ambition sufficient to push it to its utmost stretch, will at some time, spring up among us? And when such a one does, it will require the people to be united with each other, attached to the government and laws, and generally intelligent, to successfully frustrate his designs….

Distinction will be his paramount object, and although he would as willingly, perhaps more so, acquire it by doing good as harm; yet, that opportunity being past, and nothing left to be done in the way of building up, he would set boldly to the task of pulling down….

I first came across these quotations in an article by Jeffery Rosen published in the Wall Street Journal.  The Grumpy Doc does not need to add anything further to them and will leave them for your thought and consideration.

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