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5
JAMES DELANCEY
Graft in New York: The Early Years (1703–1760)

“A Chief Justice known to be of an implacable temper is a terrible thing in this country.”

— Cadwallader Colden about James DeLancey

William Marcy Tweed, Huey Long, William Lorimer, Richard Daley, Tom Pendergast: all famous (or if you prefer, “infamous”) political leaders known in America as “bosses.” All of them were successful to varying degrees. And yet none of them could touch the successes enjoyed by America's first political boss. Colonial New York Governor James DeLancey just had a flair for bastardry unlike any other.

DeLancey wrote the book on building a political machine and trading influence in American politics. He was a political animal from his birth in 1703. His father was a prosperous French Huguenot, and his mother was the daughter of New York City's first native-born mayor Stephen Van Cortlandt. Educated in England, handsome, intelligent, and witty, DeLancey had a wide network of familial alliances and set about making even more of them, His tutor at Cambridge eventually became Archbishop of Canterbury. He married an heiress with connections to prominent London politicians. His sister married British Admiral Sir Peter Warren. Warren was the hero of the Siege of Louisbourg, a battle where British forces took the strongest French fort in the Western Hemisphere. This coup carried Warren into politics. Once established, he used his influence to help along his brother-in-law's political career.

With the help of his family and friends, DeLancey accomplished a great deal as a young man. He was appointed to New York's Governor's Council at twenty-six. At twenty-eight he'd won a seat on the New York Supreme Court. By thirty he was chief justice. Over the years DeLancey packed the Governor's Council with his own allies. He distributed political favors through his network, building the foundation of a formidable political machine.

WHAT'S THAT WORD? “BOSS”

In his book
A Study in Boss Politics: William Lorimer of Chicago
, author Joel Arthur Tarr defined the phrase “political boss” as “a dictator who represented special and corrupt interests and who violated the rights of ‘the people'.” Bosses controlled political machines, organizations that did their bidding and shared in the profits (both legal and illegal) that their activities produced.

Efficient and tireless, DeLancey got things done. On the other hand, he could also be a bitter political foe. According to fellow Supreme Court Justice Cadwallader Colden, New York now had a chief justice who used “the power of his office to intimidate” those who opposed him. DeLancey's incessant political maneuvering even resulted in New York's royal governor naming him chief justice for life in 1744. His powerbase now secure, DeLancey began laying plans for his next move: securing the governorship of New York. In 1753 he got it. At times he was “royal governor.” Other times, he was “acting governor.” The title mattered less than the power.

James DeLancey controlled the executive branch of New York's colonial government until his death in June of 1760. Because of his life-appointment as chief justice of a colonial court packed with his cronies, he also controlled the New York judiciary. And because he spent his first ten years in politics building alliances among both New York City's aldermen and the members of the colonial assembly, he also controlled the colonial legislature. After James DeLancey's death, any political boss that followed could only dream of hitting such a trifecta. Others would work from DeLancey's playbook, but none would ever succeed as he had. DeLancey died of natural causes, still clutching the strings of power, still holding office, still wealthy, and never having served a day in jail.

6
GEORGE WASHINGTON
Tenth Commandment? What Tenth Commandment? (1732–1799)

“'Tis true, I profess myself a Votary to Love — I acknowledge that a Lady is in the Case — and further I confess that this Lady is known to you. — Yes Madam, as well as she is to one, who is too sensible of her Charms to deny the Power, whose Influence he feels and must ever submit to.”

— George Washington

Shakespeare? Nope. Wordsworth? Nah. Who is the author of this intensely romantic passage? None other than our most famous president: George Washington. And he didn't write it to his wife, or to just any one of his previous sweethearts. He wrote it as part of an intriguing letter to his best friend's wife.

Before he was president, before he chaired the Constitutional Convention, before he was commander-in-chief of the Continental Army, before he was “George Washington,” George Washington was in love with a married woman named Sally Fairfax.

Sally was married to wealthy landowner George William Fairfax. Washington knew the couple through his elder brother Lawrence, who was married to Fairfax's sister.

Washington wrote many letters to Sally, always hinting at something he shouldn't talk about. Later in the same letter quoted above, Washington mentions the futility of his affections, using the same oblique language: “[B]ut experience alas! Sadly reminds me how impossible this is.” Still later he hints that there is only one person who can make him happy. He teases that Sally knows this person. He also refers to
Cato
, a contemporary stage play that they had both seen, saying, “I should think my time more agreeable spent believe me, in playing a part in Cato … & myself doubly happy in being the Juba to such a Marcia as you must make.” This last remark is the most telling. In
Cato
, Juba is a North African prince who is secretly, hopelessly, passionately in love with the title character's daughter, Marcia. Washington obviously had quite a thing for the young, beautiful, popular, and worldly Sally.

BASTARD ON THE MAKE

Not only was the “Father of his Country” a horny bastard trying to score with his best friend's wife, he was also perpetually on the lookout to “improve his situation.” Speculating in land, romancing girls from wealthy families, and eventually marrying the richest widow in the colony, George Washington was a man on the make before he was the “Man on Horseback.”

Did Sally return Washington's affection? We know that they spent much time together, and often outside of the company of her much older husband. The Fair-faxes were the most frequent visitors to Mount Vernon after Washington's marriage. The would-be lovers exchanged letters for the remainder of their lives, even after Washington married and after Sally and her husband moved to England in 1773.

In a much later letter, Washington told Sally how much her company had meant to him. He wrote of how he had “never been able to eradicate from my mind those happy moments, the happiest in my life, which I have enjoyed in your company.” The fact of the matter is that whether or not Washington took liberties with Sally, he eventually moved on, married Martha (one of the wealthiest women in Virginia), and by all accounts had a good marriage. Far from being the stolid, “marble statue” that history so often makes of our leaders, Washington was naturally fiery, passionate, and given to great flights of fancy.

So go figure, George Washington, the marble man on horseback, the boring guy on the dollar bill, likely had an affair with his hot young neighbor, and went on to “marry up.” Talk about an overachiever! Who knew the guy had so much in common with Bill Clinton?

7
BENEDICT ARNOLD
America's First Traitor (1741–1801)

“Let me die in this old uniform in which I fought my battles. May God forgive me for ever having put on another.”

— Benedict Arnold's last words

To this day the name of Benedict Arnold is synonymous with the word “traitor.” But who was Benedict Arnold really? Was he as big a bastard as popular history makes him out to be?

Truth be told, Benedict Arnold nearly died in the Battle of Saratoga in 1777. Had he perished on the field that day, he would have come down to us second only to George Washington in esteem. He would likely have been held in wide regard as the greatest battlefield commander on either side of the Revolutionary War.

That said, he was still unquestionably a bastard.

A prosperous Connecticut merchant and experienced sea captain during peacetime, by 1777 Arnold was also a seasoned battlefield commander. Twice-wounded veteran of the seizure of Fort Ticonderoga, the assault on Quebec, the naval battle on Lake Champlain, and a host of other engagements, and George Washington's favorite general.

But even before turning traitor Arnold was a bastard. He possessed a knack for making enemies, and was often accused of corruption and profiteering. He could, at least, foist the blame on his prewar business success operating as a smuggler evading British import duties. But Arnold was also touchy about his honor, had a short fuse, and had fought a number of duels. And as he was never reimbursed for the fortune he spent outfitting troops, Arnold wanted to make back his investment and then some.

By the time Arnold was in command of the American fortifications at West Point in 1780, he was more desperate for new sources of income than ever. He used his young, free-spending wife's loyalist family connections to set up a meeting at which he agreed to turn over West Point to the British. Only the capture of the British officer with whom Arnold had met foiled the plot.

A GLORIOUS BASTARD

In October 1777, the American forces under General Horatio Gates had bottled up the main British force under command of General “Gentleman Johnny” Burgoyne within a day's ride from Albany. On October 7, a pitched battle began at Bemis Heights, near Saratoga, New York. When Arnold saw that the second American charge against the British was turning into a rout, he borrowed a horse, rallied the retreating troops, and led them on a heroic bayonet charge into the teeth of murderous British musket fire. Arnold's horse was shot out from under him at the end of the battle. Both the musket ball and the fall shattered his left leg. A controversial decision to set the bone rather than amputate left Arnold with a left leg that was two inches shorter than his right one.

Arnold escaped to the British, who gave him a general's commission and a cash bonus of $6,000. Although he commanded some British troops later in the Revolution, as a turncoat he was hardly welcomed with open arms. After the British withdrawal in 1783 Arnold left the United States, never to return.

So while it's true that Arnold was heroic, it is also important to remember his capacity for resentment, his thin skin, and his eye for a way to make a buck.

When he was being taken to the rear after his leg was shattered by that musket ball at Saratoga, Arnold is rumored to have remarked, “Better it had been in the chest.” If he actually said it, he never said anything more correct during his entire life.

8
HORATIO GATES
The “Conway Cabal” and the Plot to “Get Rid” of George Washington (ca. 1727–1806)

“Beware that your Northern laurels do not change to Southern willows.”

— General Charles Lee to General Horatio Gates after his victory at Saratoga

Ever wonder what might have happened to our country if George Washington got himself replaced as commander-in-chief of the Continental Army? Well it almost happened. And the bastard responsible was British-born Horatio Gates.

At first Gates hardly seemed like an opportunist. When the war broke out in 1775, the British Army veteran left his Virginia plantation. He offered his services to George Washington and was made made adjutant general of the Continental Army.

As the top staff officer, Gates had made good use of his talents for organization and discipline learned during his twenty years in the British Army.

Two years later in 1777, British General John Burgoyne's entire army surrendered to Gates after the Battle of Saratoga. He simply took much of the credit owed his subordinate, Benedict Arnold, for their success against the British.

Where Gates was riding high, the fortunes of the Continental Army's Commander-in-Chief George Washington were at a low ebb. Washington lost popularity in Congress, having spent most of 1777 and 1778 fighting a series of losing battles all over New Jersey while trying to pry the British Army out of Philadelphia.

Gates saw the window of opportunity and leaped. He had his despicable aide James Wilkinson begin a whisper campaign suggesting that Washington had lost the confidence of both Congress and his own troops. The plot culminated with several letters written by an Irish-born French Army veteran officer named Thomas Conway. Each complained about Washington's perceived shortcomings and implied that Gates stood ready to take over as an able commander-in-chief. The letters were forwarded to certain members of Congress to provoke a decision against Washington and for Gates. The Conway Cabal “plot,” such as it was, didn't amount to much.

Conway resigned in disgrace once his letters and their contents were made public. One of Washington's staff officers challenged Conway to a duel, and shot him for his trouble. Conway survived to apologize to Washington and return to France.

There was one more moment in history when it looked as if Gates might succeed Washington. He had maneuvered his Congressional allies into naming him to Washington's staff by 1783, when hostilities with the British were largely over. The Continental Army was camped at Newburgh, New York, at the time, keeping an eye on the British in New York City. Restless and owed years of back pay, many of the officers of the army began to mutter about how they ought to march down to where Congress was in session and insist on receiving their pay. When Washington got wind of this, he made it clear that he would not allow the army to influence civilian political decisions in that manner.

At that point several of Gates's aides began to circulate more whispers among the disaffected officers. They pushed the notion that if Gates replaced Washington, the former would be open to airing their complaints much more forcibly with the Congress. And thus the so-called “Newburgh Conspiracy” was born.

In the end the Newburgh Conspiracy had no more success than the Conway Cabal did. Washington crashed a meeting chaired by Gates, gave his celebrated “Newburgh Address,” which moved most of those assembled to tears, and effectively broke up the plot before it had a chance to gain any traction among the troops. And as a result the republic was spared a military coup at the beginning of its existence.

Horatio Gates: bastard.

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