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Questions to ask Alexander Hamilton

9 min read

The best questions for Alexander Hamilton (born 1755 or 1757, died 1804) go past the musical to his own papers: the hurricane letter that got him out of St. Croix, his artillery company in 1776, the 51 Federalist essays he wrote, the Treasury reports of 1790 and 1791, the Reynolds pamphlet and the duel with Aaron Burr. This page gives 24 questions in six groups, what the documents show, sample answers in his words and the traps to avoid.

The musical is a starting point, not a source

Most students meet Hamilton through the 2015 Broadway musical. It gets the outline right and many details wrong, so an interview built on it will repeat its errors. Check your questions against this table first.

What the musical suggestsWhat the record shows
He was born in 1757, aged 19 in 1776His birth year is uncertain. A 1768 probate record on St. Croix implies 1755; Hamilton himself later used 1757. Historians are split.
Hamilton and Burr were rivals from their first meetingThey were lawyers and occasional allies in New York for years; the real break came in the 1790s and the 1804 governor's race.
Angelica Schuyler gave up Hamilton for her sisterAngelica was already married to John Barker Church when Hamilton married Eliza in December 1780.
He was an abolitionistHe was a founding member of the New York Manumission Society (1785) and backed arming enslaved men for freedom, but records show he also bought and sold enslaved people for his in-laws and probably his own household (Jessie Serfilippi, 2020).
He threw away his shot on purposeBefore the duel he wrote that he meant to throw away his first fire. What happened on the ground at Weehawken is disputed by the two seconds' accounts.

Questions about the Caribbean childhood

  • 1. Your father left the family and your mother died when you were a boy. Who looked after you?
  • 2. You ran a trading house's books on St. Croix as a teenager. What did that work teach you about money?
  • 3. In 1772 you wrote a newspaper letter about a hurricane. How did that letter change your life?
  • 4. What did you see of slavery in the sugar islands?

What the record says: Hamilton was born on Nevis to Rachel Faucette and James Hamilton, who were not married. His father left in 1765; his mother died in February 1768. He clerked for the merchants Beekman and Cruger in Christiansted. His hurricane letter appeared in the Royal Danish American Gazette in October 1772, and local backers paid for him to study in North America. He enrolled at King's College (now Columbia) in New York.

Questions about 1776 and the war

  • 5. Before you were twenty you wrote pamphlets against a Loyalist clergyman. What were you arguing?
  • 6. In March 1776 New York made you captain of an artillery company. How did a student get that job?
  • 7. What was the year 1776 like for you, from the defence of New York to the crossing to Trenton?
  • 8. Why did you accept a post as General Washington's aide in 1777 instead of a field command?
  • 9. What happened when you led the night attack on Redoubt No. 10 at Yorktown?

What the record says: A Full Vindication of the Measures of Congress (December 1774) and The Farmer Refuted (February 1775) answered Samuel Seabury. Hamilton was commissioned captain of the New York Provincial Company of Artillery on 14 March 1776. His guns served in the New York campaign of 1776 and at Trenton (26 December 1776) and Princeton (3 January 1777). He joined Washington's staff as a lieutenant colonel on 1 March 1777 and led the assault on Redoubt No. 10 at Yorktown on 14 October 1781. For a wider view of that year, see our America 250 founders guide.

Questions about the Constitution and The Federalist

  • 10. On 18 June 1787 you spoke for about six hours and praised the British constitution. Why did that speech hurt your reputation?
  • 11. You wrote 51 of the 85 Federalist essays in about seven months. How did you divide the work with James Madison and John Jay?
  • 12. Why did you want a strong single executive?
  • 13. Why did you call the courts “the least dangerous” branch?

What the record says: notes by James Madison and Robert Yates record his proposal for a president and senators serving “during good behaviour”, in effect for life. The Federalist essays ran in New York papers from October 1787 to May 1788 under the name “Publius”. No. 70 defends energy in the executive; No. 78 argues for judicial review. At the New York ratifying convention in Poughkeepsie in 1788 he helped win a narrow vote for the Constitution.

Questions about the Treasury

  • 14. Why did you insist on paying the war debt at full value, even to speculators?
  • 15. How was the deal over assuming state debts tied to placing the capital on the Potomac?
  • 16. Why did a country of farmers need a national bank?
  • 17. In the Report on Manufactures you argued for helping factories. Why did Congress ignore most of it?

What the record says: he became the first Secretary of the Treasury on 11 September 1789. The Report on Public Credit (January 1790), the bank proposal (December 1790), his opinion on the bank's constitutionality (February 1791) and the Report on Manufactures (December 1791) are his main papers. The Compromise of 1790 is known mainly from Thomas Jefferson's later account of a dinner with Hamilton and Madison, so treat its details as one man's memory.

Questions about enemies, scandal and the duel

  • 18. Why did you publish the details of your affair with Maria Reynolds in 1797?
  • 19. Why did you and John Adams, both Federalists, end up hating each other?
  • 20. Your son Philip died in a duel in 1801. Why did you still accept Burr's challenge three years later?
  • 21. You wrote that you opposed duelling. Why go to Weehawken at all?

What the record says: the so-called Reynolds Pamphlet admitted the affair to clear him of charges that he had speculated with Treasury funds. His 1800 pamphlet attacking Adams split the Federalists; our Hamilton vs Adams comparison covers that feud. Philip was shot by George Eacker in November 1801. Burr's challenge followed remarks reported in a newspaper during the 1804 New York governor's race. They met on 11 July 1804; Hamilton died the next day. Joanne Freeman's Affairs of Honor (2001) explains why a public man felt he could not refuse.

Questions about slavery

  • 22. In 1779 you backed John Laurens's plan to free enslaved men who fought. What did you argue?
  • 23. You helped found the New York Manumission Society. What did it do?
  • 24. Records show you handled sales of enslaved people for your Schuyler in-laws. How do you square that with your words?

What the record says: his letter to John Jay of 14 March 1779 argues that enslaved men would make good soldiers and that freedom should come with the musket. The Manumission Society (1785) campaigned for gradual emancipation in New York, which began by law in 1799. Jessie Serfilippi's 2020 study for the Schuyler Mansion State Historic Site found entries in his own cash books for buying and transferring enslaved people. A strong answer holds all three facts together.

Sample answers in Hamilton's words

On question 12 (a strong executive):

“Energy in the Executive is a leading character in the definition of good government.”
The Federalist No. 70, March 1788

On question 10 or any question about why government is needed at all:

“Why has government been instituted at all? Because the passions of men will not conform to the dictates of reason and justice, without constraint.”
The Federalist No. 15, December 1787

On question 21 (the duel): use the statement he wrote before 11 July 1804, in which he said he was opposed to duelling on religious and moral grounds and intended to throw away his first fire, and perhaps his second. Paraphrase it and name the document; the full text is on Founders Online.

On question 22: from the letter to John Jay of 14 March 1779, he argued that the natural abilities of Black men were as good as those of white men, and that giving them muskets and freedom together would be both just and wise. Quote it only after reading the full letter.

Questions he could not have answered

  • Anything about the musical, the ten-dollar bill or the Federal Reserve (created 1913).
  • How the duel ended, if your Hamilton speaks from before 11 July 1804.
  • Whether he was born in 1755 or 1757. He was not sure himself, or chose not to say.
  • Modern arguments that use his name for or against today's policies. Ask about the debates of the 1790s instead.

Practise before you present

Hamilton talked fast and argued hard, which makes him a good partner for rehearsing follow-up questions. You can try that with an AI recreation of Alexander Hamilton on Yuga by voice or text. It is built from his writings, but it is not Hamilton and can get things wrong. Quote The Federalist and his papers in your work, never the recreation.

Where to read Hamilton's own words

  • The Federalist Papers, free on Project Gutenberg. Start with Nos. 1, 15, 70 and 78.
  • Founders Online (founders.archives.gov): the full Papers of Alexander Hamilton, including the Treasury reports, the Laurens and Jay letters and the pre-duel statement.
  • The Library of Congress holds the Alexander Hamilton Papers, his main manuscript collection.
  • Jessie Serfilippi, “As Odious and Immoral a Thing” (Schuyler Mansion State Historic Site, 2020), for the slavery records.

For the planning side of an interview project, see our historical figure interview guide.

Questions people ask

What are good questions to ask Alexander Hamilton?
Ask how a hurricane letter got him out of St. Croix, what he did as an artillery captain in 1776, why he wrote most of The Federalist, why he wanted a national bank, why he published the Reynolds pamphlet, and why he met Aaron Burr at Weehawken despite saying he opposed duelling. Tie each question to a date or document.
What did Alexander Hamilton do in 1776?
On 14 March 1776 he was commissioned captain of the New York Provincial Company of Artillery. His company served in the defence of New York that year and in the attacks on Trenton (26 December 1776) and Princeton (3 January 1777). In March 1777 he became an aide to the commander in chief with the rank of lieutenant colonel.
How accurate is the Hamilton musical?
It follows the main events of his life but changes dates, compresses relationships and invents scenes. Angelica Schuyler was already married when he met Eliza, Burr was not a lifelong enemy, and the musical plays down his ties to slavery. Use it for interest, then check every fact against his papers.
How many Federalist Papers did Hamilton write?
Historians credit him with 51 of the 85 essays, with James Madison writing 29 and John Jay 5. Authorship of a dozen essays was once disputed between Hamilton and Madison, and most scholars now give those to Madison. The essays appeared in New York newspapers from October 1787 to May 1788.

Sources