Alexander Hamilton

by Ron Chernow

During the robust era of Progressive Republicanism, marked by brawny nationalism and energetic government, Theodore Roosevelt took up the cudgels and declared Hamilton “the most brilliant American statesman who ever lived, possessing the loftiest and keenest intellect of his time.”

A small revolution in consumer tastes had turned the Caribbean into prized acreage for growing sugarcane to sweeten the coffee, tea, and cocoa imbibed in fashionable European capitals. As a result, the small, scattered islands generated more wealth for Britain than all of her North American colonies combined.

“’Tis a very good thing when their stars unite two people who are fit for each other, who have souls capable of relishing the sweets of friendship and sensibilities. . . . But it’s a dog of [a] life when two dissonant tempers meet.”16 When the time came for choosing his own wife, he would proceed with special care.

He spoke of his father in a forgiving tone, tinged with pity rather than scorn. “It was his fault to have had too much pride and too large a portion of indolence, but his character was otherwise without reproach and his manners those of a gentleman.”23 In short, Hamilton saw his father as amiable but lazily inept.

Perhaps from this exposure at an impressionable age, Hamilton harbored a lifelong reverence for Jews. In later years, he privately jotted on a sheet of paper that the “progress of the Jews . . . from their earliest history to the present time has been and is entirely out of the ordinary course of human affairs. Is it not then a fair conclusion that the cause also is an extraordinary one—in other words that it is the effect of some great providential plan?”

This early exposure to the humanity of the slaves may have made a lasting impression on Hamilton, who would be conspicuous among the founding fathers for his fierce abolitionism.

Let us pause briefly to tally the grim catalog of disasters that had befallen these two boys between 1765 and 1769: their father had vanished, their mother had died, their cousin and supposed protector had committed bloody suicide, and their aunt, uncle, and grandmother had all died. James, sixteen, and Alexander, fourteen, were now left alone, largely friendless and penniless.

Because he maintained perfect silence about his unspeakable past, never exploiting it to puff his later success, it was impossible for his contemporaries to comprehend the exceptional nature of his personal triumph.

In fact, this apparent attraction to two opposite types of women—the pure and angelic versus the earthy and flirtatious—ran straight through Hamilton’s life, a contradiction he never resolved and that was to lead to scandalous consequences.

She was the type of woman Hamilton found irresistible: pretty, coquettish, somewhat spoiled, and always ready for flirtatious banter.

With fewer than twenty-five thousand inhabitants, New York was already second in size among American colonial cities, behind Philadelphia but edging ahead of Boston.

“The first political piece which [Hamilton] wrote,” recalled Troup, “was on the destruction of the tea at Boston in which he aimed to show that the destruction was both necessary and politic.”37 This anonymous salvo may have been the “Defence and Destruction of the Tea” published in John Holt’s New-York Journal.

Like other founding fathers, Hamilton would have preferred a stately revolution, enacted decorously in courtrooms and parliamentary chambers by gifted orators in powdered wigs.

One scandalized British soldier complained that the American riflemen “conceal themselves behind trees etc. till an opportunity presents itself of taking a shot at our advance sentries, which done, they immediately retreat. What an unfair method of carrying on a war!”

base servile tool,

He expressed views of leadership that closely anticipate his later dicta about the need for decisive, unequivocal action: “In public exigencies, there is hardly anything more prejudicial than excessive caution, timidity and dilatoriness, as there is nothing more beneficial than vigour, enterprise and expedition.”

I am going into the army and perhaps ere long may be destined to seal with my blood the sentiments defended by my pen. Be it so, if heaven decree it. I was born to die and my reason and conscience tell me it is impossible to die in a better or more important cause.”35

Throughout his career, Hamilton was fastidious about military dress, insisting that his men be properly attired. “Nothing is more necessary than to stimulate the vanity of soldiers,” he later wrote. “To this end a smart dress is essential. When not attended to, the soldier is exposed to ridicule and humiliation.”

Later on, as a major general, Hamilton instructed his officers on the need to be personally involved in drilling and training their men.

As dozens of barges disgorged British and Hessian troops into the hilly, wooded area, the patriot forces lost their nerve and began to flee in undisguised terror, discarding any semblance of discipline. On horseback, an outraged Washington tried to stem the disorderly retreat. Though Washington was famous for his composure, his infrequent wrath was something to behold, and he cursed the panic-stricken troops and flailed at incompetent officers with his riding crop. Finally, he flung his hat on the ground in disgust and fumed, “Are these the men with whom I am to defend America?”

In fewer than five years, the twenty-two-year-old Alexander Hamilton had risen from despondent clerk in St. Croix to one of the aides to America’s most eminent man.

Perhaps from unfulfilled paternal instincts, Washington had several surrogate sons during the Revolution, most notably the marquis de Lafayette, and he often referred to Hamilton as “my boy.”

In fact, Washington wasn’t nonchalant and could be exacting and quick to take offense. While he had a dry wit, his mirth was restrained and seldom expressed in laughter. He did not encourage familiarity, fearing it would encourage laxity in subordinates, and held himself aloof with a grave sobriety that gave him power over other people. In addition, over time he became such a prisoner of his own celebrity that people couldn’t relax in his presence.

It was temperamentally hard for Alexander Hamilton to subordinate himself to anyone, even someone with the extraordinary stature of George Washington.

In commenting to Morris, Hamilton foreshadowed his later views, arguing that the election for governor “requires the deliberate wisdom of a select assembly and cannot be safely lodged with the people at large.”

Many people were struck by Hamilton’s behavior at Monmouth, which showed more than mere courage. There was an element of ecstatic defiance, an indifference toward danger, that reflected his youthful fantasies of an illustrious death in battle. One aide said that Hamilton had shown “singular proofs of bravery” and appeared “to court death under our doubtful circumstances and triumphed over it.”

This early lesson in Realpolitik—that countries follow their interests, not their sympathies—was engraved in Hamilton’s memory, and he often reminded Jeffersonians later on that the French had fought for their own selfish purposes. “The primary motives of France for the assistance which she gave us was obviously to enfeeble a hated and powerful rival by breaking in pieces the British Empire,” he wrote nearly two decades later. “He must be a fool who can be credulous enough to believe that a despotic court aided a popular revolution from regard to liberty or friendship to the principles of such a revolution.”

Hamilton brushed aside the fallacies that slaves were not smart enough to turn into soldiers and were genetically inferior: “This is so far from appearing to me a valid objection that I think their want of cultivation (for their natural faculties are probably as good as ours) joined to that habit of subordination which they acquire from a life of servitude will make them sooner become soldiers than our white inhabitants.”

“The truth is I am an unlucky honest man that speaks my sentiments to all and with emphasis. I say this to you because you know it and will not charge me with vanity. I hate congress—I hate the army—I hate the world—I hate myself. The whole is a mass of fools and knaves. I could almost except you and [Richard Kidder] Meade. Adieu. A. Hamilton.”

For all his supposed sophistication about womanly wiles, Hamilton was completely hoodwinked by Mrs. Arnold’s brazen charade. As always, he was hypersensitive to female charms, and well-bred ladies in distress especially brought out his chivalry.

The rupture with Washington highlights Hamilton’s egotism, outsize pride, and quick temper and is perhaps the first of many curious lapses of judgment and timing that detracted from an otherwise stellar career.

Completion of the second trench snuffed out the last remnants of resistance among the British. Cornwallis had grown so desperate that he infected blacks with smallpox and forced them to wander toward enemy lines in an attempt to sicken the opposing forces. He knew that he lay in grave peril and wrote to Sir Henry Clinton, “My situation now becomes . . . critical. . . . [W]e shall soon be exposed to an assault in ruined works, in a bad position, and with weakened numbers.”

Increasingly Hamilton despaired of pure democracy, of politicians simply catering to the popular will, and favored educated leaders who would enlighten the people and exercise their own judgment.

Compared to the raucous commercial chaos of New York, Philadelphia was a more orderly place, abounding in elegant homes tucked tidily behind garden walls.

Until age fifty, Madison, the oldest of ten children, lived in economic dependence on his father and even in Congress fell back on income from the family plantation. Like Jefferson, he could not escape his dependence on slavery, whatever his private qualms, and told his father during his last year in Congress that unless the delegates got a pay raise, “I shall be under the necessity of selling a Negro.”

He then staged the most famous coup de théâtre of his career. He was about to read aloud a letter from a congressman when the words swam before his eyes. So he fished in his pockets for his glasses. “Gentlemen,” he said, “you will permit me to put on my spectacles, for I have not only grown gray but almost blind in service to my country.”47 The mutinous soldiers, inexpressibly moved, were shamed by their opposition to Washington and restored to their senses.

Many artists who painted Hamilton picked up the quiet smile that suffused his ruddy cheeks and shined in his close-set blue eyes, conveying an impression of mental keenness, inner amusement, and debonair insouciance.

He preferred wits, satirists, philosophers, historians, and novelists from the British Isles: Jonathan Swift, Henry Fielding, Laurence Sterne, Oliver Goldsmith, Edward Gibbon, Lord Chesterfield, Sir Thomas Browne, Thomas Hobbes, Horace Walpole, and David Hume.

Alexander and Eliza also rescued a thirty-five-year-old painter, Ralph Earl, who had painted battle scenes of the Revolution and studied under Benjamin West in London. Upon returning to New York in 1786, Earl lost his money in dissolute habits and was tossed into debtors’ prison. Moved by his plight, Hamilton induced Eliza “to go to the debtors’ jail to sit for her portrait and she induced other ladies to do the same,” wrote James Hamilton. “By this means, the artist made a sufficient sum to pay his debts.”

He had expressed an unwavering belief in the genetic equality of blacks and whites—unlike Jefferson, for instance, who regarded blacks as innately inferior—that was enlightened for his day. And he knew this from his personal boyhood experience.

In 1786, when he owned more than two hundred slaves, he refused to break up families and swore not to buy another slave. “There is not a man living who wishes more sincerely than I do to see a plan adopted for the abolition” of slavery, he told Robert Morris.31 Washington emancipated his slaves in his will and even set aside money to assist the freed slaves and their children.

Who were these solons rhapsodized by Benjamin Franklin as “the most august and respectable assembly he was ever in in his life”?44 The fifty-five delegates representing twelve states—the renegade Rhode Island boycotted the convention—scarcely constituted a cross section of America. They were white, educated males and mostly affluent property owners. A majority were lawyers and hence sensitive to precedent.

One story, perhaps apocryphal, claims that when Hamilton was asked why the framers omitted the word God from the Constitution, he replied, “We forgot.” One is tempted to reply that Alexander Hamilton never forgot anything important.

The delegates solved this baffling riddle by deciding that all states would enjoy equal representation in the Senate (a sop to small states) while representation in the House of Representatives would be proportionate to each state’s population (a sop to large states).

In exchange, southern states agreed that the importation of slaves might cease after 1808, feeding an illusory hope that slavery might someday just fade away. Without the federal ratio, Hamilton glumly concluded, “no union could possibly have been formed.”87 Indeed, the whole superstructure erected in Philadelphia rested on that unstable, undemocratic foundation.

Hamilton and Morris felt a mutual affinity, flavored with some hearty cynicism. Morris admired Hamilton’s intellect even as he reproved him for being “indiscreet, vain, and opinionated.”96 Repaying the compliment, Hamilton called Morris “a man of great genius, liable however to be occasionally influenced by his fancy, which sometimes outruns his discretion.”97 On another occasion, Hamilton branded Morris “a native of this country, but by genius an exotic.”

Hamilton and Morris were discussing how Washington signaled to people that they should maintain a respectful distance and not behave too familiarly with him. Hamilton wagered Morris that he would not dare to accost Washington with a friendly slap on the back. Taking up the challenge, Morris found Washington standing by the fireplace in a drawing room and genially cuffed him on the shoulder: “My dear general, how happy I am to see you look so well.” Washington fixed Morris with such a frigid gaze that Morris was sorry that he had ever taken up Hamilton’s dare.

With the possible exception of James Madison, nobody had exerted more influence than Hamilton in bringing about the convention or a greater influence afterward in securing passage of its sterling product.

It would long seem contradictory—and, to Jeffersonians, downright suspicious—that Hamilton could support a document that he had contested at such length. In fact, the Constitution represented a glorious compromise for every signer. This flexibility has always been honored as a sign of political maturity, whereas Hamilton’s concessions have often been given a conspiratorial twist. For the rest of his life, Hamilton remained utterly true to his pledge that he would do everything in his power to see the Constitution successfully implemented.

The rancor ushered in a golden age of literary assassination in American politics. No etiquette had yet evolved to define the legitimate boundaries of dissent. Poison-pen artists on both sides wrote vitriolic essays that were overtly partisan, often paid scant heed to accuracy, and sought a visceral impact.