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17
JAMES WILKINSON
A New and Improved Benedict Arnold (1755–1825)

“The most finished scoundrel that ever lived.”

— John Randolph

Everyone has heard of Benedict Arnold and Aaron Burr, neither of whom was very successful in his treasonous endeavors. But there were successful ones, too, villains like America's greatest traitor James Wilkinson. Wilkinson was born to a wealthy Maryland family in 1755 and was studying medicine in Philadelphia when the Revolution broke out. He eagerly set aside his studies and enlisted for service in the Continental Army. He took part in Washington's encirclement of Boston, and served as a staff officer with Arnold at the Siege of Quebec. He even jumped to General Gates's staff in time to take part in the victory at Saratoga in 1777.

Wilkinson, however, also took part in the Conway Cabal against George Washington, which did nothing to endear him to his army superiors. Within a year even Gates had gotten fed up with Wilkinson and forced him to resign his commission. Wilkinson returned to active service as a supply officer in 1779. He was again forced to resign again, this time in the face of charges of corruption. It was the first of many times he would fight such allegations.

Whatever his crimes in the army, Wilkinson had big plans for profit on the civilian front. In 1784 he met with the Louisiana Territory's Spanish governor, Esteban Rodriguez Miró. They plotted to seize a trade monopoly on the Mississippi River for Kentucky. Wilkinson took bribes from the Spanish and promised to help Kentucky declare its independence. He argued that an independent country of Kentucky could act as a buffer between Spanish colonies and the land-hungry United States. The citizens of Kentucky might even consent to union with the Spanish territories.

By the late 1790s Wilkinson was back in the army. This time he was a commissioned general stationed on the Southwestern frontier. Still a Spanish spy, he passed much information along to the Spanish regarding American aims on New Orleans.

It was years before any of this came to light. Seen as a loyal career officer, Wilkinson was eventually appointed Louisiana's first territorial governor. He ruled from New Orleans as a virtual military dictator. A number of prominent citizens complained about his methods to the national government. President Jefferson then ordered a full investigation of Wilkinson's conduct. Wilkinson, however, was more than prepared. He turned over information about the territorial ambitions of former Vice President Aaron Burr as a way of saving his own skin.

It worked. Burr went on trial for treason and Wilkinson testified against him. Wilkinson's testimony made such an impression that Virginia Democrat and prosecutor John Randolph said, “Wilkinson is the only man I ever saw who is from the bark to the very core a villain!”

Wilkinson served without distinction in the War of 1812 and then retired to write his memoirs (which should have been shelved in the “fiction” section). He died in Mexico in 1825, hoping to make a fortune bringing American settlers into the sparsely populated Texas region.

It is fitting that one of America's most successful traitors died and was buried outside of the country. It is especially ironic in light of the fact that Wilkinson was never caught in his lifetime. His involvement with the Spanish did not surface until the 1850s, when his letters to the Spanish governor in New Orleans were published.

This is, of course, why Wilkinson was more successful than any other traitor on an enemy payroll. When James Wilkinson died in Mexico at age seventy, he had been suspected of all manner of corruption. But no one in the government or out-side of it suspected his long association (for pay) with the Spanish. That is the very definition of a successful spy, and one of the definitions of an outright bastard.

“[Wilkinson was] a general who never won a battle or lost a court-martial.”

— Robert Leckie, historian

18
AARON BUR
Successful Duelist and Failed Secessionist (1756–1836)

“Burr is sanguine enough to hope everything — daring enough to attempt everything — wicked enough to scruple nothing.”

— Alexander Hamilton

In 1800 Thomas Jefferson won the presidency by the thinnest of margins in a vote that had to be settled in the House of Representatives. He almost lost the presidency to a brilliant, restless polymath named Aaron Burr, who became vice president according to electoral law at the time. Before the end of Jefferson's second term Burr would stand trial for treason; he was the only member of the U.S. executive branch to ever do so.

Burr was born in New Jersey in 1756, the grandson of the great Puritan minister Jonathan Edwards. His legal studies were interrupted by the outbreak of the American Revolution. Like many he volunteered for service with the Continental Army. By the end of the Revolution, Burr had distinguished himself by rising to the rank of colonel. He held a number of political offices in short order, then in a senatorial election 1791 he defeated one of New York's incumbent senators Phillip Schuyler. Burr and Schuyler's son-in-law Alexander Hamilton had been friends up to that point, but after the election became bitter enemies.

Their falling-out helps explain Hamilton's public support for Jefferson during the election of 1800. In Hamilton's view, Jefferson placed the public good before his own interests. He saw Burr, on the other hand, as a dangerous opportunist who placed his own interests before anyone else's.

Burr eventually grew bored by the vice presidency, and in 1804 he decided to run for governor of New York. Shortly afterward Hamilton made some cutting remarks about Burr's character. Burr then challenged his former friend to a duel.

The two fought in Weehawken, New Jersey, and Hamilton was killed. Burr faced murder charges in both New York and New Jersey for a time. The allegations forced him to hide out while the hullabaloo over Hamilton's death blew over. Eventually the charges were dropped, and Burr went back to his normal routine.

When Burr's term of office as vice president ended in 1805, he headed west. He had leased 40,000 acres of land in Texas, and claimed that he planned to build on that initial piece of land.

The truth wasn't so simple.

Burr's plan did include building, but he also intended to “filibuster” (lead a private military expedition) into Mexico. Though his design was illegal, it may not have actually been treasonous. And he might have managed to take the land he wanted had he not told so many people the secret. Burr had traveled far and wide, mentioning different bits of the plan to a host of people, many of whom he hoped to involve in his plot (including a Tennessee militia general named Andrew Jackson).

So when James Wilkinson claimed that Burr in fact intended to also peel off a number of the Western states in the Union and produced letters written by Burr to that effect, the accusation didn't seem unfounded. Burr once again found himself in hot water. Just as he had done after he killed Hamilton, Burr went to ground. This time, however, a federal arrest warrant issued by President Jefferson himself caught up with Burr, and he was arrested in what is now Alabama.

Burr was charged with treason in a federal court in Virginia in 1807 and faced death for his intended crimes. President Jefferson had publicly declared that Burr was guilty, thereby attaching the president's personal prestige to the widely held belief in Burr's guilt. But the evidence against Burr was largely circumstantial, and his lawyers destroyed Wilkinson's credibility as a witness. Once again found not guilty, he walked.

Burr spent most of the rest of his years roaming the world, a restless spirit for the remainder of his long life, fleeing creditors and chasing opportunity. At age seventy-seven he married a wealthy widow whose inheritance he quickly ran through, just as he had any money that had ever come into his hands. Burr died, on the day his divorce from his second wife became final, aged eighty, a bastard to the end.

19
THE FEDERALISTS
The Hartford Convention and the Lousy Timing of Treason (1814)

Secession movements don't play well in this country. Just look at what happened to the Southern gentlemen who voted to secede from the Union in 1860 and 1861. The national government fought a long and bloody war in which more Americans died than in all of the other wars in which Americans have served and fought
combined
.

And to think, that civil war could well have been fought four decades earlier, beginning in 1814, if the pack of bastards who convened the infamous “Hartford Convention” had gotten their way. Here's what happened.

In 1800 Thomas Jefferson and the Democratic Republicans swept the Federalist Party from power. The Federalists lost both the White House and Congress to their mostly Southern and Western rivals. At the same time, the United States was fighting to prosper as the Napoleonic Wars raged across Europe. Both the British and the French had violated American neutrality time and time again. As soon as he was in office, Jefferson began to retaliate against both sides of this conflict with a trade embargo of all European goods. The United States, he said, would prosecute an “economic war” and deny the British and the French one of their largest emerging markets.

Since shipping and shipbuilding were New England's largest industries, the embargo was an unqualified disaster for the region. As a result the state governments of all five New England states were soon solidly Federalist. Jefferson's successor James Madison stepped into office in 1809. He extended Jefferson's economic policies so far as that he actually started the War of 1812 with Britain over the issue. He also curtailed the defensive abilities of New England's state governments. These five troubled states were seen by most of the rest of the country (especially the South) as being potentially disloyal.

Turns out the rest of the country was right.

By late 1814, New England's economy was in shambles, and no end to the war was in sight. A group of prominent Federalists led by Harrison Gray Otis called for a convention of delegates representing all five New England states to meet in secret in Hartford, Connecticut, in December 1814.

BASTARD PROPOSAL

The delegates wrote up a proposal that called for the national government to pass the following constitutional amendments:

1. Limit all embargoes to less than sixty days.

2. Revoke the Southern right to count slaves as three-fifths of citizen for the purpose of determining representation in the Congress.

3. Limit future presidents to a single term.

4. Require a two-thirds Congressional majority for declaration of war, disruption of foreign trade, or admitting a new state to the Union.

5. Bar incoming presidents from being from the same state as their immediate predecessors (All of the presidents to that point, with the brief intermission of John Adams's administration from 1797–1801, had been Virginians. This was intended to end the so-called “Virginia Dynasty”).

There was no way that the Republican-controlled Congress would have passed any of the amendments the Convention advocated. This proposal was only intended to be a bargaining chip to get the rest of the country to take New England seriously. The New Englanders wanted other states to negotiate with their state governments, as opposed to continuing to ignore their collective concerns.

A month later the Hartford Convention adjourned and sent representatives to Washington, D.C. By this time, word of Andrew Jackson's victory at New Orleans, and the signing of the treaty that ended the war, had reached the District of Columbia.

Could their timing have been worse?

The Hartford Convention finished what the election of 1800 had started and signaled the death (by suicide) of the Federalist Party. After the brief honeymoon of the Era of Good Feeling, sectionalism in America would return with a vengeance. Over the next forty-five years internal bickering would help drag the country spiraling into the Civil War so narrowly avoided in 1815.

The Federalists: proof that if you can be a bastard, “Timing” can be a bitch!

20
HENRY CLAY
The “Corrupt Bargain” and the Election of 1824 (1777–1852)

“I'd rather be right than president.”

— Henry Clay

If ever Kentuckian Henry Clay told a lie, it was in the above quote. The man wanted to be president with every fiber of his being. Charismatic, shrewd, several times U.S. Senator and Speaker of the House of Representatives, Clay spent decades seeking the Oval Office, running for president three different times, the first time in 1824.

By 1824 President James Monroe was facing retirement. He had no like-minded Virginia aristocrat serving as his secretary of state and positioned to continue the “Virginia Dynasty.” The unnerving (for other states, especially in New England) and steady flow of Virginians through the executive branch began with Thomas Jefferson, was carried on by James Madison, and seemed destined to end with Monroe himself. Thus the election of 1824 promised to be the most open one so far in the short history of the young republic.

This is not to say that Monroe's actual secretary of state did not harbor presidential ambitions or that he wasn't capable. In many ways John Quincy Adams, who had entered public life while in his teens, was the ablest secretary of state that America has ever produced.

But Adams lacked the “common touch.” In 1824, ever more liberal voter registration laws were allowing more and more of the “unwashed masses” — in other words, the poor — to vote. The common touch was becoming a political necessity. And no politician in the United States typified the “everyman” more than former militia general, Indian fighter, frontier judge, and U.S. Senator Andrew Jackson of Tennessee. As if these two larger-than-life statesmen weren't enough, there were several other candidates for the presidency in that year of change; among them was Henry Clay.

The ensuing campaign was remarkable for its viciousness. Not since the election of 1800 when the elder Adams lost to Jefferson had the nation seen such vitriol spewed between competing political camps.

Jackson easily won a majority of the popular vote, but he failed to gain a majority of either states or electoral votes. The deadlock passed the election decision to the House of Representatives for a tiebreaker vote. And Henry Clay was Speaker of the House.

WHY THE BASTARD DID IT

Clay and Adams had known and disliked each other for over a decade, having worked closely together as members of the American peace delegation that negotiated the end of the War of 1812 in Ghent, Belgium. But if Clay disliked Adams, he despised Jackson and feared the Tennessean's appeal to the “mob.” Clay had decided long before the House convened to settle the election question in 1825 that he was going to throw his support behind Adams; the question was what he would receive in return. The answer: he would be secretary of state, a position considered — at the time — to be the stepping-stone to the presidency.

Clay and Adams claimed that although they met several times before the House vote, no promises were made and no favors done. But shortly after Clay swung the votes to ensure Adams's victory, Adams announced that he intended to make Clay his secretary of state. Since every president from Jefferson onward to the younger Adams had served as secretary of state, Adams had essentially acknowledged Clay as his political heir.

It did Clay no good in the end. Jackson ran again in 1828 and cleaned Adams's clock. Clay would go on to continue a distinguished career in the Senate and earn the nickname “The Great Compromiser.” But he would never get closer to the presidency than he had in 1824 when he sold out Andrew Jackson.

“The Judas of the West has closed the contract and will receive the thirty pieces of silver…. Was there ever witnessed such a bare faced corruption in any country before?”

— Andrew Jackson on Henry Clay and the “corrupt bargain” of 1824

BOOK: The Book of Bastards
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