Brilliant and Reckless? Alexander Hamilton’s Lessons for Modern Leaders.

“History,” notes presidential biographer Ron Chernow, “is long, messy and complicated.” 

Few figures embody that truth more than Alexander Hamilton — a striving immigrant from the West Indies who rose to become George Washington’s chief of staff, shaped the U.S. Constitution, created the nation’s financial system, and ultimately died in a duel with the vice president.

His improbable rise has inspired both scholars and Broadway audiences, but for Scott C. Miller, economic historian and assistant professor at the University of Virginia’s Darden School of Business, Hamilton is more than a cultural phenomenon.

“He is emblematic of America in both the best and worst ways,” Miller says. “Driven, innovative and ambitious — but also plagued by hubris and poor judgment.”

That tension between brilliance and recklessness is at the heart of Miller’s new course, ‘His Name is Alexander Hamilton’: Lessons in Management, Strategy and Leadership. Launching this fall for Executive MBA and part-time MBA students, the course explores how Hamilton’s strengths and failures can serve as case studies for today’s leaders.

Why Hamilton, Why Now?

“Hamilton is probably the most prominent founding father right now, thanks to Lin-Manuel Miranda’s musical,” says Miller, who is also director of the Democracy and Capitalism Lab at the UVA Karsh Institute of Democracy and a senior fellow at the Miller Center of Public Affairs.

More than that, there are “a lot of very Darden-centric lessons” that can be learned from Hamilton.

“He was the first secretary of the Treasury and built the first financial system of the U.S. He worked very hard to create the basis for a modern industrial economy,” says Miller. “But at the same time, he made a lot of really bad decisions that threatened both his professional ambitions and his personal life. It’s important to learn not just from the successes of famous figures, but also from their failures.”

What makes Hamilton such a compelling figure is that many students can relate to some of his circumstances. “He was young, very driven, incredibly intelligent, but also flawed,” Miller says.

To say Hamilton’s beginnings were far from auspicious is an understatement.

“Hamilton is the quintessential American story,” Miller says. “It sounds cliché, but he was a penniless orphan in the Caribbean. At that particular time, if you weren’t part of the elite planter class, a Caribbean sugar island was about the worst place in the world you could come from.”

And yet he succeeded against formidable odds to become, as Miller puts it, “at the barest of minimums, the second-most powerful man in the country.”

Hamilton’s Strengths: Systems Builder and Administrator

Hamilton was really, really smart.

“I don’t use the word brilliant very often,” says Miller, “but I think Hamilton was truly brilliant. He had a very specific type of genius: it was Steve Jobs brilliant, as opposed to Einstein brilliant.”

Meaning Hamilton was able to synthesize vast amounts of information and adapt it to very specific contexts.

Miller calls this “systems-building genius.”

One example of this genius is America’s financial system, which he created. Miller breaks it into three parts, with accompanying cases: First, Hamilton dealt with the catastrophic state of American credit following the Revolution. Second, he created the financial system, including the first national bank, the Bank of the United States. And third, he promoted a system of industrial production.

“None of these things were new — other countries had national banks and different schemes for enhancing public credit. America was the one of the last to industrialize,” Miller explains. “But what Hamilton was able to do is take the various pieces and form them into a comprehensive system that became a flywheel; they reinforced each other.”

It’s worth remembering that in 1789, when Hamilton became the first secretary of the Treasury, America had no banking system to create credit, no currency that held its value and no securities market. By the time he left office in 1795, the nation had all of that.

Hamilton’s other big strength was that he was “a remarkable administrator,” says Miller. “And I mean that in the most respectful sense.”

“It’s very rare that you have somebody who’s a great, visionary CEO and, at the same time, also a brilliant COO. Those skillsets tend not to come in the same person,” he explains. “Hamilton was remarkably good at not just creating systems that work in theory, but also operationalizing and running them at peak efficiency.”

What made him a successful administrator was his ability to organize and build effective teams, although Miller acknowledges Hamilton doesn’t have a reputation as a delegator.

“In many cases, he took on way too much himself, but he understood how to send people to do certain things in different places,” he says. “To actually get the system he created running — and running well — is pretty remarkable.”

That rare blend of strategist and operator was central to his genius — and Miller reaches for a chessboard to explain it.

“To be a really good administrator, you have to see the chessboard. You have to develop and deploy actions that progress multiple objectives at the same time. You have to be able to be both strategic and tactical,” says Miller. “As a systems builder, it’s like playing chess almost blind. And that’s where the real brilliance comes in.”

What can business leaders learn from this?

Where Vision Meets Execution

The lesson lies in Hamilton’s process of analysis and his ability to marry strategy and tactics. “We tend to treat the strategic and tactical as separate things: you have to have a strategic vision and plans, but then over here is the team that deals with the individual tactics,” he says.

“What Hamilton showed us is how you have to intertwine them and build the strategic emphasis into the tactical operations, and then how you use the tactical operations to reinforce the strategic vision.”

Miller says we see this play out in the way Hamilton dealt with the nation’s money supply after America’s independence from Great Britain.

“The nation faced a profound money supply problem in ways that we cannot conceptualize today in the age of the Federal Reserve and paper money,” he says. “America was also facing debt levels that we couldn't imagine today, in relative terms.”

Hamilton understood the country needed to fix its debt problem, because if Britain invaded, America would need to borrow to defend itself. This was a strategic challenge: How to deal with the massive debt that's spread across 13 states? At the same time, people living in the country did not have a medium of transaction — they had to rely on barter to exchange goods.

Hamilton came up with a plan that refinanced the debt, converting it into securities that paid interest on a quarterly basis, instead of yearly, in gold that he was able to borrow from Europe.

“So, all of a sudden, now you're refinancing the debt, you're giving people more faith in the broader faith and credit of the United States, but you're also channeling, on a quarterly basis, hard gold into the system for people to use,” Miller says.

“As people become more trusting of the full faith and credit of the United States, those debt instruments become much more stable. And then they either serve as a medium of exchange themselves, or in concert with his creation of a banking system, they can serve as the basis for money creation within the banks themselves.”

Hamilton integrated the strategic with the tactical. “You have all of these different pieces that work together to address the bigger strategic problems, but they're created in a way that also address things that are on the complete other side of the spectrum,” says Miller.

But if Hamilton excelled at building systems for a young nation, he was far less adept at managing his own impulses.

Hamilton’s Weaknesses: Hubris and Poor Judgment

“I don’t think you could find somebody in American history who was more hubristic than Alexander Hamilton,” says Miller. “The ultimate tragedy is that he had the hubris to duel Aaron Burr and got himself killed.”

What drove the sitting vice president to engage in a deadly duel with a founding father in Weehawken, New Jersey, on July 11, 1804?

Hamilton and Burr had long been rivals, but it ultimately came down to a few words.

“Hamilton reportedly said something very nasty about Burr,” says Miller. Specifically, Hamilton called him “a dangerous man, and one who ought not be trusted with the reins of government” and hinted at a “more despicable opinion” of him.

As letters from the time show, instead of apologizing, as Burr demanded, and de-escalating the situation, Hamilton responded by quibbling over the nuances of the word “despicable.”

“That level of hubris was quite literally his downfall,” Miller says. “Hamilton had profound intellect and was formidable in many ways, but he had almost no judgment whatsoever.”

That lack of judgment surfaced not only on the dueling ground but also in his private life: he became the subject of the first sex scandal in American history after an extramarital affair with Maria Reynolds.

The liaison spiraled into blackmail when her husband, James, saw an opportunity to profit. He first demanded money to keep quiet, but later spread rumors that Hamilton was feeding him insider information on federal securities. Pressed by Congress on allegations of corruption, Hamilton defended himself by publishing an excruciatingly detailed account of the tryst that became known as the Reynolds Pamphlet.

The impact was catastrophic — for Hamilton’s wife and family and his political prospects.

As Miller explains, Hamilton’s reaction diminished his political capital exactly when he needed it most, and his “Plan on Manufactures”— his attempt to bring the agricultural American to the emerging industrial revolution — failed as a result. Also, allies, including George Washington, began to doubt Hamilton’s reliability. Finally, Hamilton opened himself up to range of investigations that would follow him to the end of his life. 

Yet even Hamilton’s most painful missteps carry enduring lessons for leaders today.

Brilliance Undone by Flaws

There are three key takeaways from Hamilton’s foibles for leaders:

Find the right mentor. Miller points out that Washington held that role for Hamilton and was able to moderate his worst tendencies.

“Hamilton had the brains, Washington had the judgment,” he says. “Whenever Hamilton was away from Washington, he would be incredibly self-destructive because his judgment was non-existent.”

Leaders should seek out mentors who have solid judgment and complementary skills.

“If you have a mentor who’s essentially you, but older, that’s not going to help you,” Miller says. “You need to have someone who is willing to call you on your failings and save you from yourself.”

Create accountability. Miller notes that Hamilton allowed himself to exist outside of the systems he created, and this is something many leaders do: create systems of accountability that apply to everyone except the person at the top.

Make sure your leadership structure holds you accountable.

Seek humility. Learn from others who extol virtues you don’t have. And if you are having trouble finding someone, pick up a copy of Lincoln’s Greatest Speech: The Second Inaugural by Ronald C. White Jr. — one of Miller’s favorite books on Abraham Lincoln.

At its close, the speech offers a moving coda that reflects Lincoln’s hope of binding up the nation’s wounds following the Civil War, framed by the famous phrases, “With malice toward none; with charity for all.”

For all his brilliance, Hamilton reminds us that even the boldest visions can be undone by unchecked hubris. His story is not just one of innovation and nation-building, but also a cautionary tale about the limits of genius without judgment — a lesson as urgent for today’s leaders as it was in the early republic.

"Hamilton one of the most brilliant and one of the greatest constructive statesmen of the era of constructive statesmanship; a man to whom this republic owes a well nigh incalculable debt" - Theodore Roosevelt (May 10, 1905)