Roger Sherman
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40 free Roger Sherman trivia questions with answers — history quiz, new questions added Oct 2026.
Roger Sherman is the founder most Americans walk past. He had almost no schooling, spoke with a country drawl, and still ended up in the room for nearly every big decision of the founding era, from the first protests against Britain to the first sessions of the new federal government. This quiz collects the best fun facts about him: the jobs he held before politics, the signatures that set him apart from every other founder, the bargain he struck when the 1787 convention was stuck, and what his famous colleagues said about him behind his back. It also follows his family, which produced a remarkable run of lawyers and politicians. It suits students meeting the Connecticut delegate for the first time, teachers looking for a quick class round, and history fans who want to know more about the quiet man standing in so many famous pictures.
30 of 40 questions with answers and explanations. Play the quiz
Q 01Which of the four great US state papers Roger Sherman signed was drafted by a Committee of Five?
Declaration of Independence
The Declaration of Independence is the most famous of the four. Sherman sat on its drafting committee, though a Virginian colleague did the writing.
Q 02A painting of Roger Sherman and four colleagues presenting their draft appears on which US banknote?
$2 bill
The $2 bill carries the scene on its back, with Sherman among the five men standing before the desk. The original canvas is 18 feet wide.
Q 03Before law and politics, Roger Sherman worked in which humble trade learned from his father?
Shoemaker
Shoemaker was Sherman's first trade, and tradition holds that he walked to Connecticut with his cobbler's tools on his back. He later passed the bar without any formal legal training.
Q 04At the Constitutional Convention, only which 81-year-old delegate was older than Roger Sherman?
Benjamin Franklin
Benjamin Franklin and Sherman were old colleagues: eleven years earlier both had sat on the five-man committee that drafted the break with Britain.
Q 05Roger Sherman's wife Rebecca Prescott was a cousin of the doctor who joined which rider's 1775 alarm?
Paul Revere
Paul Revere was captured that night, but Samuel Prescott jumped his horse over a stone wall and carried the warning on to Concord.
Q 06Roger Sherman's grandson Roger Sherman Baldwin won fame defending the African captives of which ship?
Amistad
Amistad became a 1997 film in which Matthew McConaughey played Baldwin. Sherman's grandson went on to serve as governor of Connecticut.
Q 07Which Tony-winning musical about the Continental Congress has Roger Sherman as a singing character?
1776
1776 opened on Broadway in 1969 and won the Tony for Best Musical. By coincidence, the man who wrote its songs was named Sherman Edwards.
Q 08Roger Sherman said which officer should chair the Senate, or else he would be without employment?
The vice president
The vice president kept the chair on this argument: Sherman said a senator presiding would lose his vote, while ties needing a casting vote would be seldom.
Q 09Under the 1787 deal Roger Sherman championed, each state sends how many members to the US Senate?
Two
Two per state was the final deal, though Sherman's first proposal in June 1787 gave each state just one vote in the upper chamber.
Q 10Which Founding Father wrote to his wife that Roger Sherman was an old Puritan, as honest as an angel?
John Adams
John Adams wrote the line to Abigail in March 1777, adding that Sherman was as staunch as a bloodhound and as firm as a rock in the American cause.
Q 11Roger Sherman's plan for how states are represented in Congress is best known by which name?
The Great Compromise
The Great Compromise broke the deadlock between large and small states. It is also called the Connecticut Compromise, after the state Sherman represented.
Q 12Under Roger Sherman's plan, seats in the lower chamber of Congress are divided among states by what?
Population
Population decides House seats, which pleased big states like Virginia, while equal votes in the upper chamber protected small ones like Sherman's Connecticut.
Q 13Roger Sherman led the opposition to the Virginia Plan, a big-state blueprint by which future president?
James Madison
Q 21Using his own astronomical calculations, Roger Sherman published an annual series of what in the 1750s?
Almanacs
Almanacs let the self-taught Sherman show off his mathematics, and he padded them with verse and sayings of his own.
Q 22Which county job, won in 1745, gave the young Roger Sherman the income to start buying land?
Surveyor
Surveyor was a prized post on a frontier where every new farm needed measuring, and the fees also earned Sherman a good name across the county.
Q 23Roger Sherman told the 1787 Convention it was a favourable moment for crushing which form of currency?
Paper money
Paper money lost the vote: Sherman and James Wilson moved the wording that bars states from issuing it or making anything but gold and silver legal tender.
James Madison wanted both chambers weighted toward the bigger states and fought Sherman's equal-vote Senate to the end. The pair clashed again in 1789 over the Bill of Rights.
Q 14In which city did Roger Sherman and 54 other delegates spend the summer of 1787 writing the Constitution?
Philadelphia
Philadelphia hosted the delegates in the same State House where Sherman had voted to break with Britain eleven years before.
Q 15Roger Sherman signed the 1774 Petition to the King, a plea for relief addressed to which British monarch?
George III
George III never gave the colonies a formal reply to the petition, and within months the fighting had begun.
Q 16Which Virginian is said to have remarked that Roger Sherman never said a foolish thing in his life?
Thomas Jefferson
Thomas Jefferson is credited with the compliment, which he paid in spite of Sherman's awkward manner and thick country drawl.
Q 17Roger Sherman had little formal schooling, yet he spent over a decade as treasurer of which New England school?
Yale College
Yale College later gave its self-taught treasurer an honorary degree, and Sherman ran a store nearby that catered to its students.
Q 18A marble statue of Roger Sherman, given by Connecticut in 1872, stands in which Washington landmark?
The US Capitol
The US Capitol displays statues chosen by every state for the National Statuary Hall Collection, and Connecticut picked Sherman as one of its pair.
Q 19Roger Sherman died in office as a senator in 1793 after weeks of illness diagnosed as which disease?
Typhoid fever
Typhoid fever was the diagnosis, though one newspaper of the day reported that his physician blamed his liver. Sherman died in his sleep at 72.
Q 20Roger Sherman was elected the first mayor of which Connecticut city, home to his store and his grave?
New Haven
New Haven became a city in 1784 and made Sherman its mayor; President Washington came to tea at his house there five years later.
Q 24Roger Sherman sat on the committee of thirteen that drafted which first American national charter?
Articles of Confederation
The Articles of Confederation gave every state one vote in a single chamber, and Sherman fought to keep that equal footing for the Senate at the 1787 Convention.
Q 25The Continental Association that Roger Sherman signed in 1774 bound the colonies to what action?
A trade boycott
A trade boycott was the plan: no British imports, with local committees naming and shaming violators in the newspapers.
Q 26Which future Louisiana Purchase negotiator from New York sat with Roger Sherman on the Committee of Five?
Robert Livingston
Robert Livingston never signed the document he helped draft, because New York recalled him first; his cousin Philip signed in his place.
Q 27Which Connecticut delegate and future chief justice joined Roger Sherman in proposing the 1787 deal?
Oliver Ellsworth
Oliver Ellsworth left the Convention in late August and never signed the Constitution, yet George Washington later made him the third chief justice.
Q 28At the 1787 Convention, Roger Sherman wanted the president chosen by, and answerable only to, which body?
The legislature
The legislature, in Sherman's view, should appoint the executive and keep him dependent on it; he called an independent executive the very essence of tyranny.
Q 29Roger Sherman persuaded the House to put the Bill of Rights amendments where, instead of inside the text?
At the end
At the end is where they still sit, because Sherman argued the original document should remain inviolate; their chief sponsor had wanted them woven through it.
Q 30Despite having no formal legal training, Roger Sherman held which Connecticut post from 1766 to 1789?
Superior Court judge
Superior Court judge was a post he held for 23 years, even while sitting in the Continental Congress; he had been admitted to the bar after studying law on his own.