Can Hamilton Save Our Republic (Again)?

Nate Boaz
6 min readApr 3, 2024

“History doesn’t repeat itself, but it often rhymes,” they say. This quote echoed in my mind as my wife and I sat, once again, in the dim glow of a theater, watching “Hamilton: An American Musical.” Each lyric, each note, felt like it was speaking directly to the here and now, not just echoing the past.

Why Hamilton Resonates Now More Than Ever

Lin-Manuel Miranda’s masterpiece is heralded as “America then, told by America now.” But as the curtains rose and the first chords struck, a revelation hit me: Hamilton is not just our past. It’s our present. It’s our now.

The America of Hamilton’s time, with its fierce battles for democracy and against foreign influences and authoritarian tendencies, mirrors today’s tumult. It’s not the imagery of the 13 colonies or the figure of King George III that strikes a chord. It’s the raw, unfiltered internal power struggles, the clash between those self-serving power hungry politicians seeking absolute control of our country and those fighting to preserve the freedoms of our democratic republic.

Washington’s Lesson: Gracefully Step Down

One of the play’s most poignant moments is George Washington’s decision to step down and not seek a 3rd term, a testament to the enduring value of relinquishing power for the greater good. Even though there wouldn’t be Presidential term limits in the Constitution until 1951, Washington set his own and many other U.S. Presidents followed his lead.

Hamilton, the play, celebrates this with the song One Last Time where Alexander Hamilton reluctantly helps George Washington write his farewell address. Hamilton asks, “Why do you have to say goodbye?” And President Washington responds, “If I say goodbye, the nation learns to move on. It outlives me when I’m gone.” This isn’t just theatrical drama; it’s a lesson in leadership and humility that’s sorely needed today.

In Washington’s actual farewell address, which Hamilton wrote for him, he gives Americans a clear warning about the real dangers of putting party politics above country and any one man above the laws of the land:

The alternate domination of one faction over another, sharpened by the spirit of revenge natural to party dissension, which in different ages and countries has perpetrated the most horrid enormities, is itself a frightful despotism. But this leads at length to a more formal and permanent despotism. The disorders and miseries which result gradually incline the minds of men to seek security and repose in the absolute power of an individual; and sooner or later the chief of some prevailing faction, more able or more fortunate than his competitors, turns this disposition to the purposes of his own elevation, on the ruins of Public Liberty.

Hamilton vs. Burr: A Duel Beyond the Grave

The rivalry between Hamilton and Vice President Aaron Burr is not just a historical footnote; it’s a narrative that resonates deeply in our current political landscape. Hamilton, despite his flaws, chose the republic over personal gain. Burr, on the other hand, represents the perils of unchecked ambition — a theme as relevant now as it was then.

Thomas Jefferson, perhaps one of our most important founding fathers and Presidents, might not have ever been President if it wasn’t for his political rival and patriot Hamilton. The U.S. Presidential election in 1800 is one of the most contentious and consequential in U.S. history. Vice President Thomas Jefferson defeated incumbent President and Federalist John Adams. However, Jefferson tied for electoral votes with his running mate and fellow Democratic-Republican Aaron Burr. Burr was supposed to concede and become Vice President with Jefferson as President, but Burr broke his promise and started campaigning against Jefferson to be President.

Under the terms of the Constitution at the time, the outgoing House of Representatives would need to choose between Jefferson and Burr. Each state delegation cast one vote, and a victory in the contingent election required one candidate to win a majority of the state delegations. Neither of them were able to secure a majority on the first 35 ballots of the contingent election.

Most Federalist representatives backed Burr and all Democratic-Republican representatives backed Jefferson. Hamilton, the leader of the Federalists, had nothing politically in common with Jefferson. However, he favored Jefferson over Burr because Jefferson was a man of character and values and Burr, he believed only cared about one thing — himself. Hamilton convinced several Federalists to stop supporting Burr, giving Jefferson a victory on the 36th ballot.

Hamilton wrote letters to several of his own party members to tilt the scales in favor of Jefferson. One of the letters, to Oliver Wolcott Jr, on December 16, 1800 before the run off, said the following:

It is now, my Dear Sir, ascertained that Jefferson or Burr will be President and it seems probable that they will come with equal votes to the House of Representatives…There is no doubt but that upon every virtuous and prudent calculation Jefferson is to be preferred. He is by far not so dangerous a man and he has pretensions to character.

As to Burr there is nothing in his favour. His private character is not defended by his most partial friends. He is bankrupt beyond redemption except by the plunder of his country. His public principles have no other spring or aim than his own aggrandisement per fas et nefas [by fair means or foul] If he can, he will certainly disturb our institutions to secure to himself permanent power and with it wealth.

He is truly the Cataline of America…

He is bankrupt beyond redemption except by the plunder of his country.

Sadly, this line is just as applicable to presidential politics today as it was in 1800.

If Burr was the Cataline of America, then who was Cataline? And more importantly, who is the Cataline of America today?

Warning From the Fall of the Roman Republic

Lucius Sergius Catilina or Cataline was a Roman politician and soldier who instigated a failed attempt to violently seize control of the Roman state in 63 B.C. Defeated and humiliated in a public election, he concocted a violent plot to take the consulship by force, bringing together poor rural plebs, veterans, and other senators whose political careers had stalled. He was a populist who rallied the disaffected in a conspiracy aimed to assassinate several government officials, including the consul Cicero, and take control of the government. However, the plot was uncovered by Cicero, who delivered a series of speeches, exposing and denouncing Cataline. Cataline fled Rome and eventually died in battle against the Roman army.

Over time, the name Cataline became synonymous with an overly ambitious politician who was willing to seize power at any cost, including destroying his own country in the process. Some even saw the Catilinarian Conspiracy as the beginning of the end of the Roman Republic. During the Imperial era, Cataline’s name was used as a derogatory term for dictators of ill-repute. I can think of another name that ought to replace Cataline as the epithet of all time for a self-serving power and money hungry authoritarian who is willing to destroy his country and grift off of his followers for his own personal gain.

The story of Cataline, a Roman figure who sought power at any cost, is a stark reminder of the dangers of ambition unchecked by a moral compass. Hamilton’s reference to Burr as “the Cataline of America” is a powerful warning. It’s a call to recognize and resist those who would put personal gain above public good. When Hamilton called Burr this, Burr hadn’t done his worst.

Near the end of his term as vice president, Burr blamed Hamilton for his loss in the race to become governor of New York, so he shot and killed Hamilton in an illegal duel. While Burr didn’t say, “I could stand in the middle of Fifth Avenue and shoot somebody, and I wouldn’t lose any voters…” Burr did shoot someone, our former Secretary of the Treasury, and he got away with it.

After this, Burr became unpopular and politically and financially bankrupt. He fled to the Western United States and conspired to raise a militia to seize Florida and Mexico from Spain and convince nearby states to secede from the Union to create his own American Empire with him as self-appointed Emperor. President Thomas Jefferson had Burr arrested and charged with treason but Burr was eventually acquitted. The good news is Burr left the United States and lived in exile in Europe for many years and then faded into obscurity.

Burr or Hamilton, You Choose

As we look around, it’s clear: the echoes of Hamilton’s time are palpable in today’s political arena. The play isn’t just a retelling of history; it’s a mirror reflecting our own time, our own challenges. Perhaps we could all be a bit more like Hamilton right now and put our country and our constitution above any political party or any one man.

Let’s take Hamilton’s lessons to heart. It’s time to prioritize our republic and its values over partisan gain or personal ambition. It’s time to ask ourselves: Are we on the side of Hamilton or Burr?

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Nate Boaz

Dad, dog lover, Marine veteran, Author, Ex-McKinsey Partner, Ex-Accenture SMD, Harvard MBA, USNA alum. People strat guy for the leading AI company - Microsoft.