10 Things James Monroe Loved

Don’t underestimate “The Last of the Cocked Hats.”

James Monroe might be the most experienced and least appreciated president ever. I’ll do my best to honor the overlooked memory of the fifth president with this list of ten things he loved.


From a young age, James Monroe yearned for military prestige. He found it, serving under George Washington in the Battle of Trenton. Wounded and nearly killed, he got a quick promotion to captain. Unfortunately, captains had to recruit their own soldiers back then and he fell far short of his squad goals.

That meant he spent a lot of time lobbying friends like Washington and Hamilton to find him a post worthy of his command. Hamilton wrote to his friend John Laurens that Monroe “proposes to go in quest of adventures southward. He seems to be as much a knight errant as your worship; but as he is an honest fellow, I shall be glad he may find some employment, that will enable him to get knocked in the head in an honorable way.”

His military skills were finally highlighted when James Madison tapped him to replace Secretary of War John Armstrong in the War of 1812 (apparently letting the British burn down the White House was a fireable offense.) Monroe’s steady-handed soldiering helped put the U.S. back on course, and all but ensured him the ultimate role of Commander-in-Chief where he could get knocked in the head in the most honorable way.


Monroe’s resume was jaw-dropping even before he served as Secretary of State and Secretary of War at the same time. He looked at government jobs like an all-you-can-eat buffet, and he got heaping piles of everything.

With impressive legislative, diplomatic, military, and executive experience under his belt, he had the combined experience of Bill Clinton, Hillary Clinton, and John Kerry — or Ronald Reagan, John McCain, and Condoleezza Rice.

He didn’t sit around waxing poetic about political theory and philosophy like Adams, Jefferson, and Madison because he was too busy doing his job. His many, many jobs.


Some people disagree on whether James Monroe deserves the title “The Last Founding Father” (He was 18 when the Declaration of Independence was signed and he had no role in drafting the Constitution – in fact he voted against it) but one thing is for sure: he dressed like a Founding Father.

He earned the nickname “The Last of the Cocked Hats” for his habit of wearing cocked (tri-cornered) hats and knee-breeches long after they were fashionable. His clothes saved him the trouble of having to say, “Remember the Revolutionary War? Yeah, I fought in that.


Monroe pioneered the revolutionary idea of actually spending time with his family. Where he went, they went – including revolutionary France. And unlike some other presidents (Jefferson, anyone named Adams), when Monroe was with his family he wasn’t whining that he’d rather be with a book. His love for his wife, Elizabeth, and their two daughters is why he places so highly on my ranking of the Founding Fathers as fathers.


Monroe more than doubled the size of the United States first by negotiating the Louisiana Purchase in 1803 and then by giving trigger-happy General Andrew Jackson ambiguous permission to invade Spanish Florida in 1818. Then, with the Monroe Doctrine in 1823, he basically called dibs on the entire western hemisphere. And he didn’t stop there.

He also put his name on the Eastern Hemisphere, earning himself the largest city in the world named after a president. Monrovia, the capital of the African nation Liberia, was named for Monroe after he helped found it as a place to relocate freed slaves.


James Monroe had no better friend than his mentor, Thomas Jefferson. Jefferson was 15 years older than Monroe and like a father to him, teaching him much about law and the art of politics. When Jefferson urged Monroe to move near him, Monroe bought up some land adjacent to Monticello and build himself a home so the BFFs could be neighbors.

Jefferson called Monroe “a man whose soul might be turned wrong side outwards without discovering a blemish to the world” which is a lovely compliment even though it sounds excruciatingly painful.


James I and James II, as their opponents called them, had a lot in common. I wrote a field guide to help you tell them apart in the wild. Even though they sometimes battled for the same position in politics and in their mentor Jefferson’s heart, Monroe and Madison had a deep love and respect for each other.

On his deathbed, Monroe spoke fondly of Madison and “their friendship of forty years.” In his final words on July 4, 1831 he expressed regret that he should leave the world without beholding Madison again.


Monroe rang in the “Era of Good Feelings” after the Federalist Party dissolved and The War of 1812 ended. He reinstated several things Jefferson and Madison had undone, like a national bank and a standing army, which helped win over the approval of his rivals. While the burnt out White House was being rebuilt, he went on a goodwill tour throughout the country which made him even more popular – so popular in fact that he ran unopposed for re-election, the only president to do so besides Washington.

The “Good Feelings” didn’t last long. His second term showed that the two party system, for all its faults, can actually be superior to a one-party system where a lack of direction lead to political in fighting and chaos. But for a hot minute, the country was unified and he was beloved.


While serving in France, Monroe scooped up loads of Louis XIV and Louis XV chairs and more that were looted from the homes of aristocrats during the French Revolution. Not only did he get them at bargain basement prices, but he paid for them with U.S. land certificates.

After the White House was torched in the War of 1812, Congress appropriated $20,000 for replacement furniture. The Monroes pocketed $9,000 of that themselves in exchange for their own furniture, and ended up going way over budget on new stuff from France. Their buyers had problems getting mahogany (Napoleon wanted it all for himself) and “great difficulty in getting clocks without nudities.” It truly must have been an Era of Good Feelings if the biggest problem was finding clocks without boobs.


Monroe was widely regarded as friendly and good-natured, but he was more than willing to strike back if attacked. When George Washington – the most popular man in America – recalled Monroe from his diplomatic service in France for not being neutral enough, Monroe responded with a 400-page attack on Washington called “A View on the Conduct of the Executive.”

Later that year, Monroe was ready to defend himself against another Founding Father. Alexander Hamilton thought Monroe leaked proof of his affair with Maria Reynolds, and he coyly challenged him to a duel. Monroe’s no-nonsense reply was “I am ready get your pistols.” He didn’t have time for Alexander’s crap. Or proper sentence breaks. Ironically, their duel was prevented by Aaron Burr, who I’m guessing took Monroe aside and said, “No, let me kill him.”

Monroe’s defensive prowess didn’t diminish with age. When President Monroe was 73, his Treasury Secretary William Crawford called him a “damned infernal old scoundrel” and raised his cane as if to strike. Monroe quickly grabbed the tongs from the fireplace to defend himself. Crawford backed down and apologized before the President had a chance to barbecue him.

Here’s further proof that Monroe’s role in history is overlooked: Even though that duel with Alexander Hamilton was prevented by Aaron Burr, James Monroe doesn’t even get a mention in Hamilton: An American Musical.

Among the Founding Fathers he was a strong, dependable, and honest leader – but apparently not something to sing about.

For more presidential passions, check out:
10 Things George Washington Loved
8 Things John Adams Loved
10 Things Thomas Jefferson Loved 
8 Things James Madison Loved

James Monroe: The Last Founding Father by Harlow Giles Unger
The Diary of John Quincy Adams
President Monroe’s Acquisitions by Clement E. Conger and Betty C. Monkman Connoisseur, May 1976



  1. Caitie
    May 1, 2017 / 8:05 pm

    I've never understood myself why a couple people aren't at least mentioned in passing in the musical "Hamilton". The main two are Baron von Steuben and James Monroe. Although, to be fair, almost dueling Hamilton wasn't exactly a unique honor — the man challenged something like eleven people to duel in his lifetime, but the Burr duel was the only one to actually see a dueling ground. It was also the only duel that Hamilton didn't initiate. The one time the dude isn't a complete hot head, and it kills him.

    • Howard Dorre
      May 1, 2017 / 8:13 pm

      I think Baron von Steuben's life is just begging for a musical! For now I'll have to settle for the fact that the parade in Ferris Bueller's Day Off is in honor of him.

  2. Caitie
    May 1, 2017 / 8:49 pm

    Honestly​? If someone told the Baron that his legacy, amongst the average citizen at least, was a big city-wide party, I feel like he'd be okay with that.

  3. Luca
    May 5, 2023 / 10:59 am

    I always thought of Monroe as “the dad president” he didn’t do too much, but he found promising young men and gave them cabinet positions. That added with his adorable family life and weird love of outdated clothes.

    • Howard Dorre
      May 5, 2023 / 11:04 am

      Plus he’s probably always talking about how back in his day he had to cross an icy river and walk miles in the snow just to go to battle. Add to that his fierce loyalty to his friends and his occasional temper, and I’m sold. Monroe = dad president.

  4. bananna
    January 8, 2024 / 5:35 am


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