James Monroe: The Hats Story

James Monroe came to office with more executive, legislative and diplomatic experience than any previous POTUS.

JM: The Fellow In A Tricorn

James Monroe (1758-1831) was the last of the Virginia Triumvirate: three-in-a-row two-term Presidents serving between 1800-1824.

Considered the earliest image of James Monroe.

Born in Westmoreland County, VA, he was orphaned early but had the good fortune to be mentored by an uncle, who remained a mainstay throughout his life. That included a solid education, including attending the College of William and Mary for a year that coincided with the American Revolution. James Monroe, along with most of his classmates, were quick to leave the academic world for military service.

Athletic and a superb horseman, he became a scout for fellow Virginian General Washington, earning praise and promotion, and a rare letter of commendation from GW himself. A Colonel by twenty-one, he was wounded, and returned to Virginia to recuperate. But once recovered, he found it difficult to find a colonelcy in the army again, since he did not have the personal funds to recruit a regiment.

Another mentor, Thomas Jefferson

Thus he returned to academics, heeding his uncle’s advice to read law with Virginia’s Governor: Thomas Jefferson. The association proved not only beneficial, but became a personal and political close friendship for the rest of their lives.

JM: The Public Service Hat

Practically sidestepping a career in legal practice, James Monroe entered public service. As the Revolutionary War evolved into a conglomeration of United-ish States under the Articles of Confederation, the young attorney became a state legislator, serving in Virginia’s House of Delegates and later in the Congress of the Confederation.

When ex-Governor Jefferson was dispatched to France for diplomatic service, Monroe was forced by economic need to focus on his legal career, became an attorney for the State of Virginia, and won another term in the House of Delegates.

The Articles of Confederation were finally dissolved following the Constitutional Convention, and Monroe, named to Virginia’s ratifying convention, straddled a middle ground between the proponents James Madison and General Washington, and the opponents, Patrick Henry and George Mason. It was, in its way, a battle of titans and giants.

Nevertheless, the differences and concerns were ameliorated, and Monroe was named to serve as one of Virginia’s first Senators. As political divisions began to emerge in the fledgling United States Congress, Monroe remained loyal to Jefferson and Madison, and took a leadership role in the Senate.

JM: The Diplomatic Hat, Part 1

Young diplomat James Monroe

President George Washington was firmly committed to a path of neutrality for the USA, which had neither resources or experience for global partisanships. By the 1790s, GW straddled his battles by naming John Jay (an anglophile) as Minister to Great Britain, and James Monroe (a francophile) as Minister to France, Thomas Jefferson’s old post. Monroe proved a little more partisan in the francophile department than GW liked, and was eventually recalled.

Monroe returned to Virginia, and renewed his mild efforts in law practice, and his stronger inclination toward Virginia politics. He became its Governor, serving two non-consecutive two-year terms. (Even today, Virginia statue does not permit a governor to serve a second consecutive term.)

The political divisions begun in the early 1790s, had manifested seriously by the time George Washington retired in 1797. Throughout the term of John Adams, Monroe concentrated on Virginia.

JM: The Diplomatic Hat, Part 2

The Emperor

Jefferson’s election in 1800 was enthusiastically supported by Monroe, and resuscitated his diplomatic career. Once Monroe’s gubernatorial term was concluded, Jefferson sent him back to France, this time to help negotiate the Louisiana Purchase, which literally doubled the size of the United States. Then he sent Monroe to Spain to try to purchase West Florida from Spain. That effort failed. Then.

Then Monroe donned another diplomatic hat, serving as ambassador to Great Britain, specifically hoping to quell the growing difficulty of British impressment of US sailors. That effort also failed. He remained in Britain until the election of James Madison.

While Monroe’s decade in Europe offered him a cosmopolitan lifestyle and broadened outlook, it also caused somewhat of a rift between him, Jefferson and Madison. Their relationship was strained for two or three years.

JM: Dual Cabinet Hats

President James Madison

By 1811, James Monroe’s friendship with Madison had resumed, and the new President, having inherited many headaches on the diplomatic front, tapped Monroe as his Secretary of State, acknowledging his many years of practical experience in foreign affairs. Despite demanding British cessation of attacking and seizing American merchant ships, the new Secretary realized that nothing short of war would bring success.

He now became a War Hawk.

James Monroe

The War of 1812 was a travesty on several fronts. Americans had not been engaged in warfare for nearly forty years. Most of their generals had died; those remaining were aged. Weaponry had not been substantially improved in forty years either. Nor were battle strategies and tactics.

Now in his mid-50s, Monroe was one of the “young fellows.” When the Secretary of War resigned, Madison asked Monroe to wear an extra “hat.” The Senate balked, and Brigadier General John Armstrong assumed the War Hat. His intransigence in refusing to fortify and defend Washington DC, even when it became clear that it was the British objective, caused his forced resignation.

Monroe once again donned the Secretary of War hat, but the Senate was still balky about the two hats. So Monroe resigned his State hat. But no successor for State was forthcoming, and Monroe ostensibly wore the two hats for several months.

By 1816, James Monroe’s wartime leadership and energy made him the heir apparent to Madison. The old Federalist party was nearly moribund, and other challengers were younger – and could bide their time.

James Monroe creamed the opposition in the election, and was presented with one more hat. He wore that one for eight years.


Cresson, W.P. – James Monroe – UNC Press, 1946

Unger, Harlow Giles – The Last Founding Father – DeCapo Press – 2009





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