Thomas Jefferson was not only a law mentor and political ally to James Monroe, but eventually his Albemarle County neighbor. The two men were friends for many years and their political careers aligned in many ways. Current Monticello and former Highland guides Olivia Brown, Alice Wagner, Ariel Armenta, and Richard Ferguson, explore that history in this episode.


Kyle Chattleton: This is Mountaintop History, a podcast produced by the Thomas Jefferson Foundation at Monticello.

Olivia Brown: Mountaintop History brings forward meaningful stories from this historic home and plantation — from the past and from the present.

Kyle Chattleton: My name is Kyle Chattleton.

Olivia Brown: And I'm Olivia Brown.

Kyle Chattleton: Thank you for joining us. We hope you'll learn something new.

Olivia Brown: This week's episode is the second of our four-part Jefferson and Friendship Series, and we'll be looking at the long friendship between Thomas Jefferson and James Monroe. Part One of this series about Jefferson's friendship with Benjamin Franklin is also available now on our website,

Joining me on today's podcast, however, are three other Monticello guides who have also had the opportunity, like I have, to work at Highland, the home and plantation of fifth president James Monroe. So I'm excited to welcome Alice Wagner, Ariel Armenta, and Richard Ferguson to Mountaintop History.

The long friendship between Thomas Jefferson and James Monroe started as far back as either late 1779 or early 1780, and was a relationship of deep-held mutual respect. Not only did Jefferson serve as Monroe's law mentor and political ally, but the two eventually became neighbors, when Jefferson convinced Monroe to purchase land in Albemarle County. The plantations of Jefferson and Monroe sit just over two miles from each other, a short horse (or car) ride away.

During the early years of their friendship, Monroe stood in the shadow of Jefferson, learning from him, but not known on a national stage in the same way. While James Monroe was a student at the College of William and Mary, Thomas Jefferson's alma mater, he left in 1776 to join the Continental Army and fight in the American Revolutionary War. By 1779, Monroe had reached the rank of Lieutenant Colonel, but with not enough troops and listed for him to have a command, he eventually reentered William and Mary. It's there he met the sitting Governor, Thomas Jefferson, and began reading and learning the law under him.

Alice Wagner: Even very early in their professional relationship, Jefferson trusted Monroe's judgment and political understanding. In June 1780, after Jefferson sent Monroe on a special mission to report on the activity of the British army that had invaded Virginia, Jefferson asked the Governor's Council to appoint Monroe to oversee the creation of an "express" form of communication between the two men, allowing the Governor to understand what the Lieutenant Colonel was seeing closer to British military lines. Jefferson wrote to a fellow governor, Abner Nash of North Carolina, that the "situation of things in [Carolina] at present have induced me to send Colo. Monroe, a sensible, judicious, and confidential person, to the neighborhood of the hostile army, for the purpose of collecting and communicating notice of their movements..." Monroe was moved by Jefferson's trust in him for this mission, and wrote to Jefferson in September, saying, "Your kindness and attention to me and this and a variety of other instances has realy put me under such obligations to you that I fear I shall hardly ever have it in my power to repay them."

It was not long after this that Monroe's political career began to bloom. Thomas Jefferson had already been involved in the Virginia legislature and served as wartime Governor, but James Monroe's official move into the political realm came in 1782, when he was elected to the Virginia General Assembly. This began a nearly 50-year career in political service.

In June 1783, the Virginia legislature elected both Thomas Jefferson and James Monroe as two of the state's delegates to the upcoming Confederation Congress, to discuss important political and territorial matters for the new nation. Thomas Jefferson, grieving the death of his wife Martha, reluctantly accepted and for about five months, the two men shared their living quarters in Annapolis, Maryland. Jefferson's time in the Confederation Congress ended before it began, when he was appointed as ambassador to France in 1784. Joining colleagues like John Adams and Benjamin Franklin in Europe. Before he embarked on this new journey, however, he wrote a letter to James Madison, encouraging him to write to James Monroe, saying of Monroe, "the scrupulousness of his honor will make you safe in the most confidential communications. A better man cannot be." This may have been the beginning of a long friendship, not simply between Jefferson and Monroe, but among all three Virginians.

Ariel Armenta: Jefferson and Monroe corresponded frequently during the former's five years in France. It was while living in France that Thomas Jefferson completed and published his book Notes on the State of Virginia, sending copies to both Monroe and Madison to review. Notes on the State of Virginia was a comprehensive survey of the state: its plants, animals, climate; its cultural and political history; and its peoples. When he sent his copy to Monroe, he cautioned his friend against trusting the manuscript to others. In a letter explaining why, Jefferson wrote, "My reason is that I fear the terms in which I speak of slavery and of our constitution may produce an irritation which will revolt the minds of our countrymen against reformation of these two articles, and thus do more harm than good." In Notes on the State of Virginia, Jefferson laid out his views on slavery at the time, insisting that it was a foul institution that needed to, and inevitably, would end. At the same time, and using deeply racist language, he also suggested that people of Black or African descent were inferior in many respects to those of white, European descent, although he did note that his views in this regard were speculation.

James Monroe and Thomas Jefferson, like many others, realized that slavery would eventually end, but worried that if people were freed, righteous, retribution would lead them to rebel against their former enslavers. As a result, for many years, Jefferson and Monroe were dedicated to the idea of colonization - of sending freed enslaved people and others of Black, African descent, to colonize places like the Caribbean and African continent. This led to organizations like the American Colonization Society, which was dedicated to this idea of sending newly freed people back to Africa instead. Though Jefferson and Monroe believed this was the best solution to the problem of slavery, most African-Americans had no knowledge of, or family ties to, the continent of Africa itself or the Caribbean Islands, and they firmly rejected the idea. Still, the views and influence of people like Monroe on the American Colonization Society, or ACS, were clear. When the ACS established the colony of Liberia in 1820, its capital, Monrovia, was named for the man who currently sat as a United States president.

It is likely that Jefferson's projected views in support of ideas like colonization influenced Monroe's dedication to these ideas as well. When Monroe was serving as Governor of Virginia, he was notified about a major planned rebellion of enslaved people in Virginia led by Gabriel Prosser. With this knowledge, Governor Monroe sent in the local militia and thwarted the efforts of what has become known as Gabriel's Rebellion, imposing severe punishments on those involved.

Richard Ferguson: While the topics covered in the Jefferson-Monroe correspondence often focused on political issues and reports on current American topical events, they also spoke on personal matters. In 1786, while Jefferson was still serving as Minister to France, he hoped Monroe and Madison might pay a visit to Paris. Neither man ever made the trip. But Monroe explained in a letter that, "[Jefferson] will be surprised to hear that I have formed the most interesting connection in human life, with a young Lady in this town." That "Lady" was Elizabeth Kortright who would then become Elizabeth Kortright Monroe.

The personal connection between Jefferson and Monroe was clearly important to both of the men. Jefferson had hoped to create what he called a "society to our tastes," by invoking a number of his closest friends to move to Albemarle County, near his home at Monticello. His goal was to have James Madison, James Monroe, and William Short, all live in close proximity to him. At least in the case of Monroe, Jefferson was indeed successful. In February 1789, less than a year before Jefferson's return from France, Monroe acquired 500 acres in Albemarle County. They would be neighbors for many more years, until just before Jefferson's death, in 1825, when Monroe sold his Highland plantation.

Things moved pretty quickly for both men after this point. Jefferson lived in Paris during the onset of the French Revolution and witnessed the storming of the Bastille in July 1789. He returned to the United States in September and was immediately greeted with his appointment as the first Secretary of State under George Washington. By the end of 1790, Monroe was sworn in as a Virginia Senator as well. For decades, the two politicians wrote to each other about various topics. They corresponded through Jefferson's ascendence to the Presidency, and then when Thomas Jefferson retired, he relied on James Monroe to keep him abreast of what was happening in the public realm of the country. During a brief period in which Jefferson insisted that he had finally retired from what he called the "hated occupations of politics," he wrote to Monroe, "We have often wondered together, when at Philadelphia, what our friends here could mean by saying they had nothing to write about. You now see that there is nothing but complaints for want of information - for want of commerce, - weather - crops and such things you are too little of a farmer to take much interest in."

During this brief mid-career retirement Jefferson experienced, President Washington appointed Monroe to Jefferson's former post: Minister to France. The Monroes traveled to Paris in 1794, just as the Reign of Terror of Robespierre was coming to an end. Their correspondence became more infrequent, but Monroe still offered to his friend reflections on the state of politics and the ever-changing France. In July of 1796, Monroe wrote hopefully to Jefferson, "On this side of the water the scene has greatly changed for the better, in favor of republican government: for since the adoption of the New constitution liberty has as it were been rescued from the dust, where she was trampled under foot by the mob of Paris."

Olivia Brown: Jefferson's short retirement was quickly ended when he ended up as Vice President to John Adams after the election of 1796. He returned to politics, but had allies in the Democratic-Republican Party, in the form of Monroe and Madison, who helped combat the opposing Federalists. Monroe was recalled by a dissatisfied President Washington that same year, and returned to the United States with his friend and mentor having been elected to the second highest office in the country. Though James Monroe was unhappy about the recall and wanted to defend his position as Foreign Minister, it became unnecessary because he was elected Governor of Virginia in 1799. Occupying yet another position formerly filled by Jefferson, Monroe wrote about his ardent wish that Jefferson would leave Philadelphia and come back to Charlottesville, writing, "Your speedy arrival home is what I very much wish." The theme that often plagued the men's friendship continued: they tended not to be at their homes in Albemarle County at the same time.

Monroe's governorship continued for two more terms while Jefferson was busy being elected the country's third President. Of Jefferson's first inaugural address, Monroe wrote, "It is sound and strong in principle, and grateful to the opposit[e] party," a subtle note perhaps about the fact that the election of 1800 was the country's first peaceful transition of power between two different political factions.

Probably the most momentous part of the combined political careers of Jefferson and Monroe came during Thomas Jefferson's first term as President. In 1803, Jefferson made an important political move not long after Monroe's third term as Governor of Virginia ended. President Jefferson, fearing that the port of New Orleans could be closed to U.S. trade along the Mississippi River by the French, wrote hastily to Monroe, "In this situation we are obliged to call on you for a temporary sacrifice of yourself, to prevent this greatest of evils in the present prosperous tide of our affairs." Jefferson was also eager to cut down on French imperial power as soon as possible. He quickly dispatched Monroe to assist the United States' current Foreign Minister Robert R. Livingston in acquiring some kind of property from France that would protect trade on the Mississippi. Monroe was authorized to pay up to 50 livres (or roughly $9 million) for New Orleans and the Floridas. What did he come back with? Not Florida. Monroe and Livingston instead spent approximately $15 million for the Port of New Orleans and the 530 million-acre Louisiana Territory. The Louisiana Purchase catapulted the name of James Monroe to the national stage more than it had ever been. After two terms as President, Jefferson did not want nor sought a third term, but it was his two dear friends - James Madison and James Monroe - who split the nomination from the Democratic-Republican Party. Torn by the situation, he wrote to Monroe, "I have ever viewed Mr. Madison and yourself as two principle pillars of my happiness. Were either to be withdrawn, I should consider it as among the greatest calamities which could assail my future peace of mind."

Alice Wagner: 1809 brought a Madison presidency rather than a Monroe one. James Monroe's role in politics was far from over, however; he served as Secretary of State under James Madison and acting Secretary of War during part of the War of 1812, making him the only person to ever hold those two positions simultaneously. Though Jefferson was thoroughly enjoying his retirement, he did rely on Monroe to provide him with updates about the political happenings of the government. Jefferson offered his advice, but also provided Monroe with his own summaries of the state of the Union. Toward the end of Madison's presidency. Jefferson was sending Monroe clippings of local newspapers and offering to serve as a sounding board to his longtime friend and mentee.

Ariel Armenta: 1816 saw something new. No Federalist opponent was proposed to run against democratic Republican James Monroe. He rose to the presidency, winning all but three states. Jefferson, deemings his support unnecessary wrote, "I shall not waste your time in idle congratulations. You know my joy on the commitment of the helm of government to your hands." Perhaps part of the reason that Jefferson did not waste his time with these congratulations was that he had more pressing matters on which he was writing to Monroe. He intended to create a public university based in Charlottesville.

When the Board of Visitors convened for the University of Virginia on May 5, 1817, former presidents Jefferson and Madison, along with current president Monroe were all in attendance. Though Monroe was clearly occupied with leading the country, he did still play a role in the founding of Jefferson's university, including the sale of land later referred to as "Monroe Hill," that was part of the original land on which the University of Virginia was built.

Richard Ferguson: Monroe's presidency is often referred to then and now as the "Era of Good Feelings," as he was a supremely popular leader of the country. When he was up for reelection in 1820, Monroe won nearly unanimously, with only one elector not voting in his favor. That elector, William Plumer of New Hampshire, believed that the honor of a unanimous election belonged solely to George Washington, but James Monroe cultivated a similar popular sentiment during his own time in office.

After the beginning of his second term and amidst the founding of the University of Virginia, Monroe was also dealing with what Jefferson described as a "fire bell in the night" - the question of the extension of slavery throughout the United States. What became known as the "Missouri Question" was one Monroe sought to answer during his time in the White House. Jefferson wrote to him in March 1820, "This Missouri question by a geographical line of division is the most portentous one I have ever contemplated." What was the question? Whether the Missouri territory should be admitted as a slave holding state or not, and whether the federal government could dictate that result as part of a state's admittance into the Union. Known as the Missouri Compromise of 1820, the result was that Missouri would enter as a slave state, Maine as a free state, and the 36°30′ line would be delineated as the boundary for the institution of slavery. New states above it would not permit slavery, and those below it would. This agreement lasted three decades until it fell apart in the Compromise of 1850. After describing the "fire bell" to his friend, John Holmes, Jefferson said the question of Missouri, "awakened and filled me with terror. I considered it once as the knell of the Union." The question of the institution of slavery would continue and to many other presidencies, beyond those of Jefferson and Monroe.

Olivia Brown: During his second term as President, Monroe saw Jefferson's advice again. Monroe was concerned about the European imperial infringement on the colonial holdings of the Western hemisphere. President James Monroe wrote to his friend asking Thomas Jefferson if the United States should, in fact, take a role in the formation of republican principles in Latin America. In June, 1823, Monroe wrote, "Can we, in any form, take a bolder attitude in regard to it, in favor of liberty, than we did? Can we afford greater aid to that cause, by assuming any such attitude than we now do, by our example? These are subjects on which I should be glad to have your sentiments." Monroe always sought the advice of his friend and mentor. Quickly, Jefferson responded, saying, "I have ever deemed it fundamental for the United States, never to take active part in the quarrels of Europe." What has become known as the Monroe Doctrine, drafted by Monroe's Secretary of State John Quincy Adams, summarizes the two men's views: any European embroilment in Western hemispheric affairs would necessitate the involvement of the United States on behalf of burgeoning republican nations. James Monroe, President during the so-called "Era of Good Feelings," also made it known that he would be quick to defend republican ideals.

Thomas Jefferson, late in his retirement, continued to write letters to his dear friend well into his eighties. It's well-known that Thomas Jefferson and John Adams both died on the 50th Anniversary of the Declaration of Independence: July 4, 1826. Five years later, however, James Monroe also died on July 4, just in 1831. The two men had a deeply meaningful friendship that revolved around a shared respect for each other's political views, devotion to the early United States, and the long-held love of their home state of Virginia. While it's Thomas Jefferson's friendship with James Madison that is more frequently spoken of, his friendship with James Monroe was also one that held significant importance in his life.

This has been another episode of Mountaintop History, a collaboration podcast between WTJU and the Thomas Jefferson Foundation.

Kyle Chattleton: Join us for new episodes every two weeks on Apple and Google Podcasts, Stitcher, and the Virginia Audio Collective.

Olivia Brown: To learn more about Monticello or to plan your next trip, visit us online at