James Monroe Trivia
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49 free James Monroe trivia questions with answers — history quiz, new questions added Oct 2026.
James Monroe was the last Founding Father to reach the White House and the last president to wear a powdered wig and knee-breeches, which is why contemporaries called him the Last Cocked Hat. He was wounded at Trenton, shared a log hut at Valley Forge with John Marshall, studied law under Thomas Jefferson, and later fell out with James Madison before serving as his Secretary of State and Secretary of War at the same time. His presidency gave the country the Era of Good Feelings, the Missouri Compromise, the acquisition of Florida, the 49th-parallel border with Canada and the doctrine that still carries his name. He died on July 4, 1831, the third president to go on Independence Day, and Liberia's capital is named for him. These 49 questions move from the basics to the details only serious presidential buffs know: the elector who spoiled his unanimous 1820 vote, his pseudonym, his abandoned book and the price he was actually authorised to pay for New Orleans.
30 of 49 questions with answers and explanations. Play the quiz
Q 01Monroe ran two cabinet departments during which war?
War of 1812
The War of 1812 made Monroe: after the British burned the capital, the president handed him the War Department on top of State, and his record there carried him to office as the fifth president.
Q 02Monroe's presidency coincided with which famously named political period?
Era of Good Feelings
Era of Good Feelings was coined by an opposition newspaper in Boston, the Columbian Centinel, after the new president's warm welcome there on his 1817 tour of the North.
Q 03Which political party did Monroe belong to?
Democratic-Republican
Democratic-Republican by label, Monroe hoped to see political parties die out altogether, yet he still refused to appoint a single Federalist to his cabinet.
Q 04Monroe spent three years from 1780 studying which profession under Thomas Jefferson?
Law
Law held little interest for Monroe in itself: he saw it as the quickest route to wealth and influence, and in Jefferson, then governor of Virginia, he gained a mentor for life.
Q 05Monrovia, a national capital named after Monroe, is the capital of which country?
Liberia
Liberia's capital took his name in 1824 because Monroe had steered US government money to the American Colonization Society's settlement there for freed African Americans.
Q 06Monroe was born in which Virginia county, also the birthplace of George Washington?
Westmoreland
Westmoreland County was home only until his teens: orphaned by 16, Monroe became the ward of his uncle Joseph Jones, a Virginia legislator who steered him toward public life.
Q 07Monroe suffered a severed artery and nearly died in which 1776 engagement?
Battle of Trenton
Battle of Trenton nearly killed him: a musket ball in the shoulder severed an artery as he charged the Hessian guns, and only a doctor who clamped it on the spot stopped him bleeding to death.
Q 08Monroe shared a log hut at Valley Forge in 1777–78 with which future chief justice?
John Marshall
John Marshall had been his schoolmate in Virginia, and four decades after they shared that hut he administered the presidential oath to his old friend.
Q 09Which painting is said to show Monroe holding the flag?
Washington Crossing the Delaware
Washington Crossing the Delaware was painted in Germany by Emanuel Leutze, who hoped the American example would inspire Europe's reformers after 1848; the river he modelled it on is the Rhine.
Q 10Sent to Paris in 1803 with narrow instructions, Monroe instead helped close which far larger deal?
Louisiana Purchase
The Louisiana Purchase went far beyond his instructions, which covered only New Orleans and West Florida; offered the whole territory, he and Robert Livingston agreed anyway, and Jefferson backed them.
Q 11Which French ruler sold Monroe and Livingston far more land than they came to buy, for $15 million?
Napoleon
Napoleon had lost an army to yellow fever in the Caribbean and faced a new war with Britain, so he gave up his American plans and offered the whole territory to the startled envoys.
Q 12In retirement, Monroe served on the governing board of which Virginia institution?
University of Virginia
The University of Virginia stands on farmland Monroe had once owned; Jefferson founded it, and Monroe served on its board in retirement until illness forced him to give it up.
Q 13Who was Monroe's Federalist opponent in the 1816 presidential election?
Rufus King
Q 21As a young congressman, Monroe toured the frontier and helped shape which law for the lands beyond the Ohio River?
Northwest Ordinance
The Northwest Ordinance of 1787 owed something to a journey Monroe made through the western country in 1784: he came back and persuaded Congress to rethink the boundaries it had drawn for new states.
Q 22Monroe announced the Monroe Doctrine in which kind of statement?
An annual message to Congress
An annual message to Congress on December 2, 1823, carried the warning; Europe's powers largely ignored it at the time, and it was not called the Monroe Doctrine until the 1850s.
Q 23Which empire's 1821 claim to the Pacific coast of North America provoked the Monroe Doctrine's ban on new colonies?
Rufus King carried only three states: the Federalists had opposed the war just ended, were branded unpatriotic for it, and never ran a presidential candidate again.
Q 14Which of these states did Monroe lose in the 1816 election?
Connecticut
Connecticut, Massachusetts and Delaware were all the fading Federalists could hold, leaving Monroe 183 of 217 electoral votes; four years later he carried every state in the Union.
Q 15An elector from which state cast the only vote against Monroe in the 1820 election?
New Hampshire
New Hampshire's William Plumer voted for Monroe's own secretary of state instead; legend says he was guarding Washington's record as the only unanimous choice, but he is said to have simply thought little of Monroe.
Q 16Who served as vice president for both of Monroe's terms?
Daniel D. Tompkins
Daniel D. Tompkins had paid for much of New York's wartime defence on his own credit; he spent his vice presidency fighting claims that he had mishandled the money, skipping Senate sessions and drinking heavily.
Q 17Which Massachusetts man did Monroe choose as his Secretary of State?
John Quincy Adams
John Quincy Adams was picked partly to soothe Northern resentment at a run of Virginian presidents; the job made him the favourite to follow Monroe into the White House, and he did.
Q 18Which South Carolina congressman became Monroe's Secretary of War?
John C. Calhoun
John C. Calhoun was a fallback: Monroe wanted a westerner to run the War Department and turned to the South Carolinian only after his first choices said no.
Q 19Which general seized the Spanish capital of Pensacola during Monroe's 1818 Seminole campaign?
Andrew Jackson
Andrew Jackson went well beyond his vague orders, even executing two British subjects; Congress cried undeclared war, but Monroe stood by him and used the raid to press Spain into giving the territory up.
Q 20In the 1819 treaty that brought it Florida, the United States gave up its claim to which neighbouring region?
Texas
Texas was the price of Florida: Spain took no payment beyond the United States assuming up to $5 million of its own citizens' claims, but Washington had to recognise Spanish sovereignty over Texas.
Russia
Russia had decreed in 1821 that the coast down to the 51st parallel was closed to foreign ships; within months of Monroe's warning it agreed by treaty to pull its claim back north to 54°40′.
Q 24Which British foreign secretary sought a joint Anglo-American statement in 1823?
George Canning
George Canning's offer of a joint warning tempted Monroe, and two former presidents advised him to accept; his secretary of state argued America should not 'come in as a cock-boat in the wake of the British man-of-war'.
Q 25Which 1817 agreement with Britain regulated naval armaments on the Great Lakes?
Rush–Bagot Treaty
The Rush–Bagot Treaty halted a shipbuilding race that had carried on along the lakes after the last war, cutting each navy there to a vessel or two per lake.
Q 26The 1818 treaty left which region open to both America and Britain?
Oregon Country
Oregon Country lay beyond the Rocky Mountains, where the new border line stopped; unable to agree on how to divide it, the two nations left it open to both for ten years.
Q 27Which later president added a famous 'corollary' to the Monroe Doctrine in 1904?
Theodore Roosevelt
Theodore Roosevelt turned Monroe's idea on its head: a warning to Europe to stay out of the Americas became a justification for the United States to intervene in Latin America itself.
Q 28Which free state joined the Union with Missouri under the 1820 compromise Monroe signed?
Maine
Maine, until then the northern district of Massachusetts, came in free to keep the Senate balanced; Monroe had threatened to veto any bill that singled Missouri out for restrictions on slavery.
Q 29Which later measure repealed the Missouri Compromise line Monroe signed?
Kansas–Nebraska Act
The Kansas–Nebraska Act of 1854 let settlers vote on slavery north of 36°30′, where the compromise had banned it for 34 years; three years later the Supreme Court ruled the old ban unconstitutional anyway.
Q 30Which New York congressman's 1819 amendment touched off the Missouri crisis?
James Tallmadge Jr.
James Tallmadge Jr. proposed barring new slaves from Missouri and freeing those born there at 25; the House passed it, the Senate threw it out, and the sectional quarrel it started ended only with the compromise of 1820.