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‘Ardent and Affectionate’: The Friendships That Shaped Thomas Jefferson
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Cropped image of the official portrait of Thomas Jefferson, 1800, by Rembrandt Peale. Oil on canvas. White House, Washington. (Public Domain)
By Jeff Minick
3/9/2026Updated: 3/10/2026

An examination of the long life of Thomas Jefferson (1743–1826) reveals a circle of friends and acquaintances that is a veritable Who’s Who of the American Revolution and the half-century that followed. He was well acquainted with men like George Washington, made enemies of Alexander Hamilton and other Federalists, called his mentor Benjamin Franklin “a great and dear friend,” enjoyed an intellectual correspondence with Abigail Adams, and counted three presidents—John Adams, James Madison, and James Monroe—as close personal friends.

Examining his relationships with Adams, Madison and his boyhood friend Dabney Carr tells us much about Jefferson’s high regard for friendship, of which he once wrote to another friend and signer of the Declaration of Independence, Benjamin Rush: “I find friendship to be like wine, raw when new, ripened with age, the true old man’s milk, &restorative cordial.”

Apply the old proverb “Show me your friends, and I’ll tell you who you are” to Jefferson, and we gain insights into the man as well.

Friendship Means Loyalty


Monticello, Jefferson’s Virginia estate, includes the burial site of his boyhood friend Dabney Carr. (N8Allen/Shutterstock)

Monticello, Jefferson’s Virginia estate, includes the burial site of his boyhood friend Dabney Carr. (N8Allen/Shutterstock)

Born into a prominent Virginia family of landed wealth, Dabney Carr (1743–1773) received part of his early education in James Maury’s boarding school, where he and Jefferson became best friends. It’s said that the two sometimes studied or read books beneath a tall oak on the land that would become Monticello, and that they vowed that whichever of them died first, the other would bury him beneath the oak.

He and Jefferson together attended William and Mary College in Williamsburg, and during that time Carr frequently visited Shadwell, the Jefferson family’s plantation near Monticello. There he befriended and fell in love with Martha, Jefferson’s sister, and the couple married in 1765. He was active in the Virginia House of Burgesses and became a prominent opponent of British rule. Following his early death at age 29, Jefferson had him buried beneath the oak as promised, the first to be interred in what became Monticello’s cemetery.

Yet Jefferson’s fealty to his friend’s memory extended beyond the grave. He assumed the care of Martha and her six children, focusing particular attention on his nephew Peter Carr. Letters to the young man reveal Jefferson’s keen interest in his education and moral development. He urged Carr to value time, to apply himself to his studies, which Jefferson sometimes mapped out, and to “give up money, give up fame, give up science, give the earth itself and all it contains rather than do an immoral act.”

Feuding Friends


A portrait of John Adams who shared an enduring friendship with Thomas Jefferson. (National Portrait Gallery, Smithsonian Institution, Public Domain)

A portrait of John Adams who shared an enduring friendship with Thomas Jefferson. (National Portrait Gallery, Smithsonian Institution, Public Domain)

John Adams (1735–1826) and Jefferson first met in 1775 at the First Continental Congress in Philadelphia. Though Adams’ New England upbringing contrasted sharply with Jefferson’s plantation life, and he and his wife Abigail owned and operated a farm rather than a plantation, the two became fast friends, drawn together by books, ideas, and mutual respect. Later, they served at the same time as diplomats to France and England, where they toured Shakespeare’s home and English gardens together. At one point, Jefferson wrote to James Madison that Adams “is so amiable, that I pronounce you will love him if ever you become acquainted with him.”

In 1801, when the Federalist Adams lost his second term to Jefferson, the ever-widening gap in their political viewpoints and their vision for America shattered these affections. The two men ceased their correspondence, which Adams had once described as “intimate” and “one of the most agreeable Events in my Life.”

Only after Jefferson had left the White House and returned to Monticello was this breach repaired, largely through the efforts of Benjamin Rush. The 15-year correspondence from 1811 until their deaths is a treasure box of their thoughts. An anonymous author at Monticello.org observes: “This reconciliation began a rich correspondence that touched on myriad topics, from reminiscences about their contributions to the young nation’s history, to opinions on current political issues, to matters of philosophy and religion, to issues of aging. Their letters were also lighthearted and filled with affection.”

On his deathbed, while the rest of the country celebrated the 50th anniversary of American independence and the Declaration that both Adams and Jefferson had helped compose, the last words Adams spoke were “Thomas Jefferson still lives.” He was wrong, as Jefferson had died just hours earlier. He was also mistaken in another sense: Both he and Jefferson would live on in the American mind for their accomplishments, writings, and friendship.

An American Phenomenon


In the introduction to his recent book “A Journey North: Jefferson, Madison, and & the Forging of a Friendship,” Louis P. Masur writes, “There is no friendship like theirs in American history, certainly not in political history.”

Their greatest accomplishments run parallel to each other. Posterity regards Jefferson as the father of the Declaration of Independence and James Madison (1751–1836) as the father of the Constitution. Jefferson served for eight years as the third U.S. president (1801–1809); Madison held office for an identical length of time (1809–1817). Madison played a key role in the passage of Jefferson’s Virginia Statute for Establishing Religious Freedom, and both helped found the University of Virginia.

In many ways, however, the two men could hardly have been more different. At 6-foot-2, Jefferson towered above the 5-foot-4 Madison. Jefferson received his college education at William and Mary, while Madison traveled north to Princeton, in part to escape the Anglican influence that prevailed in Virginia’s education. Jefferson was fast on his feet, aflame with ideas, and engaged well with others, especially at intimate events like dinner parties. Madison was the more methodical thinker, whose painful shyness was offset only by his wife Dolley, the proverbial social butterfly.

A portrait of James Madison by John Vanderlyn. Madison and Jefferson worked closely and shared a half-century friendship. (Public Domain)

A portrait of James Madison by John Vanderlyn. Madison and Jefferson worked closely and shared a half-century friendship. (Public Domain)

Yet they forged a friendship that endured for half a century.

State politics from 1776 to 1782 put Jefferson and Madison in Williamsburg and in almost daily contact. In January 1783, Jefferson was in Philadelphia waiting to enter diplomatic service in France. He and Madison stayed in the same boardinghouse, where Jefferson acted as an ultimately unsuccessful matchmaker between Madison and Kitty Floyd, daughter of a New York congressman. When Jefferson returned from France, the next 25 years drew the two men even closer together by their politics and shared personal interests.

Books and reading, which had first drawn this odd couple together, remained a centerpiece of their conversation. Interests in liberty and government, the natural sciences, and agriculture further cemented the relationship. The creation of the University of Virginia also invited their creative energies away from the world of federal politics.

In a February 1826 letter to Madison, Jefferson wrote, “the friendship which has subsisted between us, now half a century, and the harmony of our political principles and pursuits, have been sources of constant happiness to me thro’ that long period.” In the same letter, Jefferson concluded, “to myself you have been a pillar of support thro’ life, take care of me when dead, and be assured that I shall leave you with my last affections.”

Following Jefferson’s death, Madison honored his friend’s request by keeping an eye on affairs at the university while also helping safeguard Jefferson’s reputation, assisting historians and biographers, and encouraging publication of an edition of Jefferson’s writings compiled by his grandson.

Some Lessons for Us


Among early presidents—Washington, Adams, Jefferson and Madison—friendships and rivalries helped shape the new nation. New York Public Library's Digital Library. (Public Domain)

Among early presidents—Washington, Adams, Jefferson and Madison—friendships and rivalries helped shape the new nation. New York Public Library's Digital Library. (Public Domain)

Jefferson’s life reveals the threads that make friendship work. In each of the cases mentioned, for instance, a common interest in books, reading, and ideas formed the initial pathways toward friendship. The devotion shown to Dabney Carr, and which Madison showed him, was not a false or grandiose salute to a departed friend, but a sincere sign of harmony and love. The ruptured friendship of Adams and Jefferson and its subsequent restoration tells us that personal relationships we might deem dead may still possess the breath of life.

Jefferson’s life reveals the threads that make friendship work. In each of the cases mentioned, for instance, a common interest in books, reading, and ideas formed the initial pathways toward friendship. The devotion shown to Dabney Carr, and which Madison showed to Jefferson, was not a false or grandiose salute to a departed friend, but a sincere sign of harmony and love. The ruptured friendship of Adams and Jefferson and its subsequent restoration tells us that personal relationships we might deem dead may still possess the breath of life. Here were two men who, though separated by a mountain of differences, restored and preserved a friendship they regarded as more valuable than politics.

In a May 1820 letter, Jefferson observed that “wherever I have been, it has been my good fortune to meet with or make ardent and affectionate friends.” Because these friendships shaped and benefited the early years of the American republic, the rest of us have shared in Jefferson’s good fortune as well.

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Jeff Minick has four children and a growing platoon of grandchildren. For 20 years, he taught history, literature, and Latin to seminars of homeschooling students in Asheville, N.C. He is the author of two novels, “Amanda Bell” and “Dust on Their Wings,” and two works of nonfiction, “Learning as I Go” and “Movies Make the Man.” Today, he lives and writes in Front Royal, Va.