Location: Charlottesville, Virginia, about two miles from Monticello
James Monroe’s Ashlawn-Highland is a stark contrast to Mr. Jefferson’s intellectual pleasure palace just two miles down the road. The home is beautiful, but quite small, and reflective of the gifts of its owner. As a president and a man, Monroe strikes me very much in the mold of Harry Truman or Gerald Ford. To his detractors, he was a partisan hack who put political loyalties first. To his admirers, he was a good and decent man on whom his country leaned in times of crisis without ever fully appreciating him.
Monroe’s connections with Thomas Jefferson ran deep. When the Revolution broke out, Monroe was one of the young students at the College of William and Mary who raided the Governor’s Palace and liberated the swords and muskets that were stored there. He enlisted in the Continental Army and was badly wounded in the shoulder at the Battle of Trenton, an incident recounted in fascinating detail in David Hackett Fischer’s book Washington’s Crossing. Back home in Virginia, he studied the law with none other than former governor Jefferson (himself a brilliant attorney). As a Jefferson ally, he was soon elected to the Virgina House of Delegates, the Continental Congress, and at age 32, to the United States Senate.
In 1794, Monroe was appointed U.S. minister to France at the height of the French Revolution. Like Jefferson, Monroe strongly favored the revolution but not the extreme bloody turn that it took. He acted quickly to rescue all the Americans who fell from favor and faced a potential turn at the guillotine, including Thomas Paine and Madame Lafayette. But his bent for the radical faction also earned him the ire of President Washington back home, who fired Monroe and ordered him to return home.
Politics had taken an ugly, paranoid turn as the political class, once united as the “Founding Fathers,” split apart into Hamiltonian (Federalist) and Jeffersonian (Republican) parties. As a leading Jeffersonian, Monroe was elected governor of Virginia; outside the state he was criticized by Hamiltonians as a French dupe, a Jacobin, and occasionally, a traitor. The election of 1800 was disputed between Jefferson and Aaron Burr and came down to a narrow vote in the House of Representatives. Many believed that Monroe and other middle state governors were prepared to arm their state militias and attempt to overthrow the government if Burr somehow won the election.
What makes Ashlawn-Highland a “Lewis & Clark” stop is, of course, Monroe’s next act, a critical role in the purchase of the Louisiana Territory from France. As detailed in our novel The Fairest Portion of the Globe (on sale now, click “Buy Now,” folks), Louisiana had been the pawn of France and Spain for decades, and a major impediment to the dreams of Americans like Jefferson who dreamed of westward expansion.
Around 1800, the master French diplomat Talleyrand became concerned about Spain’s weakness in North America. It was easy to see that the Americans were a rising people and would eventually overrun the Spanish territory, with or without their government’s consent. Talleyrand negotiated the cession of Louisiana back to France, though for the most part it continued to be administered by Spanish officials.
As president, Jefferson was trying to maintain cordial relations with both European powers, but the French takeover of Louisiana was a setback to say the least. It seems that Talleyrand and his boss, Napoleon, had big dreams for reestablishing a true French colonial presence in Louisiana. As Jefferson wrote to his minister to France, Robert Livingston, “There is on the globe one single spot, the possessor of which is our habitual and natural enemy. It is New Orleans, through which the produce of three-eighths of our territory must pass to market … France, placing herself in that door, assumes to us the attitude of defiance…” A inveterate hater of all things British, Jefferson began to reluctantly eye an alliance with Britain as the only way to ensure that U.S. commerce could travel freely on the seas … unless …
In 1802, Jefferson sent his old friend James Monroe to France with $2 million and an order to negotiate the purchase of New Orleans and “West Florida” (the present-day Gulf Coast of Louisiana, Alabama, Mississippi, and the Florida Panhandle) from the French. Even as Monroe was crossing the Atlantic, things were happening fast. The plans of Napoleon and Talleyrand had collapsed in the face of an unexpectedly bloody and costly uprising in Santo Domingo (Haiti). When Monroe arrived on the scene, he found the French leaders ready to smash it all for cash — not just New Orleans, but the entire Louisiana Territory, almost one million square miles of land.
Many historians believe that Napoleon and Talleyrand believed they could simply lift the Americans’ wallets, then take the territory away again by force when they got back on their feet. In any case, in a whirlwind succession of secret meetings, and without any authority whatsoever except their faith that Thomas Jefferson had their backs, Monroe and Livingston concluded the deal, purchasing Louisiana for a cool $15 million — surely one of the greatest real estate bargains in world history.
Historian John W. Foster wrote of the significance of the Louisiana Purchase this way: “It made the acquisition of Florida a necessity. It brought about the annexation of Texas, the Mexican War, the thirst for more slave territory to preserve the balance of power, the Civil War, and the abolition of slavery. It led to our Pacific Coast possessions, the construction of the transcontinental lines of railway and our marvelous Rocky Mountain development, the demand for the Isthmus Canal, the purchase of Alaska, the annexation of Hawaii … it fixed our destiny for world power.”
Not bad for two weeks’ work in a long and storied political career. Thanks, James Monroe.












