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James Monroe is most remembered for his Monroe Doctrine (it's ain't named after Marilyn). But it turns out he seems to have been involved in every significant event in American political history up to his big contribution.
For one of those old-timey presidents that tends to be forgotten alongside Rutherford B. Hayes, John Tyler, and Brendan J. Brown (who are so lost to the public imagination that you probably didn't even notice that that final name is 100% fictitious), Monroe was a powerhouse of his time.
For starters, as a young lad of sixteen he went off to fight in the Revolutionary War. Not only that, he was there with George Washington when he crossed the Delaware, during the Battle of Trenton, and the horrific winter at Valley Forge.
Bayonets and starvation at age sixteen: debatably worse that being in high school.
After the war, Monroe studied law under some dude named Thomas Jefferson, and held a few positions in Virginia government. Even though he wasn't a fan of George Washington (gasp!), the first president sent him to be the U.S. minister to France in 1794 because Monroe, like others before him, sympathized with the cause of the French Revolution.
He may have sympathized a little too much, and got recalled after two years because he convinced the French that the U.S. would never ratify the Jay Treaty with England, in a kind of wink-wink "don't worry it about it" way. (Source)
After some time as governor of Virginia, Monroe was appointed by his ol' friend Jefferson in 1803 to join Robert Livingston in his negotiations with Monsieur Napoleon, eventually leading to the Louisiana Purchase. Livingston really did the legwork, but you can still cross it off Monroe's "Famous American Events" bingo card. (Source)
Jefferson then sent Monroe along with William Pinckney to try and get England to stop kidnapping American sailors and forcing them into the British navy…because no one likes kidnapping, even when it happens on the high seas. It didn't work, hence the War of 1812. (Source)
Rising in the ranks, Monroe served as Secretary of State and later Secretary of War for James Madison between 1812 and 1817. Remember, this was during the War of 1812, which makes it a time when those jobs were extra important. In fact, he was appointed Secretary of War after the British burned down Washington, D.C., which seems to show some level of confidence in his abilities—and certainly a lack of confidence in the guy who was in charge when the capital got torched.
During his various roles in state and federal government, Monroe fell into the Jeffersonian camp of politics, meaning pro-states rights over federal government. He fought against secrecy in Congress, helping open up the proceedings for the public to see (think the early 19th-century version of CSPAN). He also established the first state-funded public school system to decrease illiteracy, and fought to build more public roads to make commerce easier.
Finally, after his turn in Madison's cabinet, Monroe was (totally unsurprisingly—have you checked out his resume?) elected president in 1817. At this point in American history, the Secretary of State was considered the standard successor to the presidency, although starting with the super-contentious election of 1824 that starts to fall apart.
If you're keeping score so far, Monroe has been involved with the War of 1812, the French Revolution, the Jay Treaty, the Louisiana Purchase, and the War of 1812. And yeah, there's still more…
When Monroe became president, it was the start of what's known as the Era of Good Feelings, a few years when political parties dissolved into one, and the country was generally more unified than before. People loved their new president, who did the first presidential tour since Washington, letting people see his sparkling personality. (Source)
One thing Monroe is repeatedly praised for is his strong choice of cabinet members. He tried to choose someone from every major region of the country, although when Henry Clay (westerner) refused the secretary of war position, the president ended up with two southerners. The final group consisted of John C. Calhoun (South Carolina) as secretary of war, John Quincy Adams (Massachusetts) as secretary of state, William Crawford (Georgia) as secretary of the treasury, and William Wirt (Virginia) as Attorney General.
One of the first major events of Monroe's presidency was the Seminole War, which started out as an effort to stop runaway slaves, and ended up with the U.S. acquiring Florida from Spain. You know, the usual progression of events. General Andrew Jackson was sent to guard the border of Florida, which had become a haven for runaway slaves assisted by the Seminole tribe, but Jackson decided to just invade and take over the local Spanish fort instead. (Typical Jackson.)
The general claimed Monroe had secretly ordered the attack, which Monroe denied, but ultimately the president never punished Jackson. The event would later come back to haunt Jackson during his own presidency, but at this point people just kind of moved on. Who hasn't taken the initiative to invade foreign territory now and again, right?
Finally, in 1819, the U.S. bought Florida in exchange for releasing claims on Texas (for a little while) and the forgiveness of Spanish debt through the Adams-Onís Treaty.
The Era of Good Feelings started to crumble in 1819, with the combination of the Missouri Compromise and the Panic of 1819. The Missouri Compromise brought up all kinds of sectional tension between north and south. Monroe actually kept his distance until Congress came up with the compromise, and pretty much just signed the bill.
As far as the Panic of 1819, the worst economic depression since the 1780s, Monroe brushed it off as a natural blip on the radar screen of any large economy. His philosophy was "this too shall pass," and he ended up being right. (Source)
Despite the depression, the Missouri crisis, and the Florida war, Monroe was the first president since Washington to be re-elected totally unopposed. Apparently, none of the other political leaders felt up to challenging Jimmy Monroe and his Supercabinet.
Fun fact: Monroe was also the first president to host a wedding in the White House, for his daughter Maria. (Source)
When British foreign minister George Canning approached the Monroe administration in 1823, trying to forge an alliance against other European countries' colonial ambitions in the New World, the president got different advice from different friends. Former presidents James Madison and Thomas Jefferson told Monroe to make the deal with Britain.
Seriously, all these guys were friends. Did they have a clubhouse somewhere?
Secretary of State John Quincy Adams insisted the president refuse, saying it would look like the U.S. was just adopting British foreign policy. JQA had also advised Monroe not to punish Andrew Jackson for his invasion of Florida. Both times, Monroe took Adams' advice. (Source)
In 1823, the president refused to make an alliance with Britain, and instead made an independent statement in his annual address to Congress (hint: it's the Monroe Doctrine). Some historians say that most of the tenets of the doctrine were essentially written by Adams...although the main points are a combination of everyone's advice. (Source)
After his second term, Monroe retired to his home in Oak Hill, Virginia, and became the regent of University of Virginia, founded by his old buddy Tommy Jefferson. As it turned out, he had spent a lot of his own money during his diplomatic trips to Europe and the presidency, and finally he petitioned to Congress for reimbursement. They paid him $30,000 in 1826 and again in 1831, which in today's dollars is well over $700,000 each time.
Phew, that's a lot of restaurant receipts to deal with.
He didn't have long to enjoy the second payment, though, because he died later in 1831 at his daughter Maria's house. Spookily, he died on July 4, just like Thomas Jefferson and John Adams (senior) in 1826.
Besides the Monroe Doctrine, the fifth president also promoted the development of lots of infrastructure throughout the country, including canals, roads, and bridges. He wanted to better connect states and create links to ports for shipping. The building program was so successful in promoting commerce that the U.S. deficit became a surplus, and Monroe was able to abolish personal taxes. (Source)
Obviously that situation did not last, or we'd all have a much more relaxing April every year.
Still, the Monroe Doctrine is by far his most enduring legacy. The speech set the stage for the direction of U.S. foreign policy, making a bold statement against European colonialism, without setting any specific plan or limitations on America's own ambitions. (Source)
The rest of American history is filled with stories about Americans holding up the Monroe Doctrine as the foundation of their actions towards other countries, for better or for worse.
Marilyn might get most of the "Monroe" glory, but James has a thing or two to brag about.