AI Alexander Hamilton takes his shot in a Darden School classroom

January 7, 2026

The Alexander Hamilton chatbot responds to Thomas Jefferson with sharp criticism and invites the UVA founder to a vigorous debate. (Illustration by John DiJulio, University Communications, assisted by AI)

For a man with a historic penchant for verbosity, Alexander Hamilton got relatively right to the point when the gentleman across the table introduced himself as none other than Hamilton’s political rival, Thomas Jefferson.

“Jefferson, is it? Well, let us not mince words. If you come wielding those pastoral fantasies of yours, know that I will meet them with the full force of urban industry and federal vigor,” Hamilton said with a touch of pomposity and hint of superiority in his voice. “But let us not yet turn this into a duel of tempers. Present your argument, and we shall see whose principles stand the test of reason and history.”

Thus began a recent colloquy between two Founding Fathers opposed in personality and belief, held in the office of University of Virginia Darden School of Business professor (and Hamilton expert) Scott C. Miller.

OK, so Hamilton and Jefferson weren’t really there. They couldn’t be. Jefferson died in 1826, 22 years after Hamilton was mortally wounded in a duel with then-Vice President Aaron Burr. The Hamilton and Jefferson confabulation involved Miller impersonating the University’s founder, and a customized chatbot of Hamilton created by Miller and Fred Telegdy, a senior instructional designer at the Darden School.

Scott Miller, left, and Fred Telegdy, right

The Alexander Hamilton chatbot is the brainchild of Scott C. Miller, a Darden School professor and Alexander Hamilton historian, and Fred Telegdy, a senior instructional designer at the school. (Contributed photos)

The custom chatbot is part of Miller’s course, Alexander Hamilton: Lessons in Management, Strategy and Leadership.

“On the final exam, students have a 10- to 20-minute conversation or debate with the custom chat in which they critique at least one or more of Hamilton’s policies,” Miller said. “But equally important, the second part of the exam is to critique the model. I am fully aware that this AI Hamilton will never be a perfect representation of him. Nevertheless, the ability to identify where it is wrong is a good demonstration of how well students ‘know’ Hamilton himself.”

The chatbot is also a way for Miller to adapt to the rise of AI in education by bringing it into his classroom.

“Especially for exams and assignments, I’ve lost all faith in my ability to determine the difference between AI doing an exam for a student and the student doing it,” Miller said. “What I wanted was for my students to actually argue with Alexander Hamilton himself. An AI recreation of him is obviously the best that we can get.”

Historical figure chatbots populate the internet. But Miller, who has a doctorate in history from UVA and is a Hamilton expert, found none of those to have a sufficient “understanding” of Hamilton’s background or exhibit Hamilton’s personality as far as Miller understands it.

“ChatGPT is polite, but Hamilton always thought he was the smartest guy in the room. He would not say, ‘That’s a great question. Let’s discuss this.’ He would dismiss opposing views as ignorant, childish or just plain stupid,” Miller said.

Discovery and Innovation: NASA selects UVA researcher for asteroid mission
Discovery and Innovation: NASA selects UVA researcher for asteroid mission

To make a better Hamilton, Miller turned to Telegdy, who has created several custom chatbots for Darden School courses. With thousands of letters, publications, books and historic documents loaded into its database, the faux-Hamilton could discuss facts and philosophy in depth.

In Miller’s office, Hamilton made it clear what he thought of Jefferson’s concern that Hamilton’s economic plan would create “an industrial, poverty-stricken wasteland like those that exist in Britain and even France.”

“Oh, spare me the lament of the rustic ideal,” came Hamilton’s quick reply. “If you fear my economic plan will reduce us to misery, then I say your vision of an agrarian paradox is a fantasy that would leave us weak and divided. Now, having delivered that sharp rebuke, let me return to reason.”

They weren’t looking to create a perfect Hamilton. Too much Hamilton could be a bad thing. He was, after all, a product of an era when perceived violations of honor could lead to the dueling grounds. If provoked or insulted enough, an accurate Hamilton AI could offer an 18th-century challenge. 

“We had to put some guardrails on it, which probably weren’t 100% historically accurate,” Telegdy said. “We had to say, ‘If you get antagonized or angry, show that, but then come back to the argument.’”

So far, no duels have been scheduled, and the AI Hamilton appears to be a success. In their final exams, students critiqued everything from Hamilton’s industrial policies and handling of the first financial panic in American history to his inability to confront slavery.

In some cases, an exam of 10 to 20 minutes evolved into a two-hour conversation.

“And that’s the point,” Miller said. “If my students can effectively debate ‘Hamilton’ using detailed and well-evidenced historical, political, economic and financial arguments, I have done my job.”

Media Contacts

Bryan McKenzie

Assistant Editor, UVA Today Office of University Communications

The Latest From Made for the USA