Alexander Hamilton's Guide to Life - Hardcover

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JEFF WILSER is the author of four books, including The Good News About What's Bad for You...The Bad News About What's Good for You, named by Amazon as one of the Best Books of the Month in both Nonfiction and Humor. His work has appeared in print or online at GQ, Esquire, New York magazine, Glamour, Cosmo, Mental Floss, MTV, and The Huffington Post. His TV appearances have ranged from BBC News to The View. He lives in New York.

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“[I] would willingly risk my life tho’ not my Character to exalt my Station.”

Hamilton’s early years are murky. Historians debate the details. Yet there can be no doubt that he’s the only Founding Father whose mother, Rachael Fawcett, was accused in court of “whoring with everyone.”

This wasn’t a happy home. This wasn’t a happy place. On the Caribbean island of St. Croix, several years before Hamilton’s birth, Rachael was “twice guilty of adultery,” according to her first husband, which, in those enlightened times, gave him the legal right to toss her into prison. So he locked her in a dungeon. (I’ve been inside the prison cell. It’s dark, hot, and has a tiny window that looks out on the clear blue sea, almost as a taunt.)

With Rachael behind bars, her husband hoped that “everything would change to the better and that she, as a wedded wife, would change her unholy way of life and live with him.” Ah, true love! He let her out of jail. Somehow the plan backfired, the dungeon failed to melt her heart, and Rachael fled and didn’t look back.

She took a ferry to an even smaller island, St. Kitts, that throbbed with the sugar and slave trades. She met a Scot named James Hamilton. On an even smaller island, Nevis, Rachael gave birth to two boys, one named Alexander. She was still married to the dungeon-master of a first husband, however, which meant that Alexander Hamilton, technically, was born a bastard. The first husband eventually filed for a separation; the divorce papers called her “shameless, rude and ungodly” and the mother of “whorechildren.”

The family soon moved back to St. Croix. The island was brutal. Alexander, or Alex, as he was called as a toddler, grew up in a land that had 90 percent of its population chained in slavery. The slaves made the sugar. “The whites lived in fear of slave rebellions. By law, every white man had to be armed with a gun, sixteen cartridges with balls, and a sword or cutlass,” explains biographer James Flexner. “To keep terror perpetually alive among the blacks, it was legislated that if a slave struck a white man, he would lose the hand he struck it with. If he drew blood, he could be executed.”

Then things took a turn for the worse.

Alex’s father went bankrupt and left home. (Historians still aren’t sure why.) Then the family got sick. Rachael caught tropical fever, confining her to a bed that would drip with blood, sweat, and vomit. The house had only one bed, which meant that Alex either slept next to his coughing mother or he slept on the floor. The doctors treated Rachael with “bloodletting” and “alcohol for her head.” He was eleven when she died. The probate court ruled that Alex would get nothing from her modest estate, as he and his brother were “obscene children.”

Then things took a turn for the worse.

Alex’s cousin volunteered to look after the boys, but for reasons still unknown he committed suicide. The legal record states that he “stabbed or shot himself to death.” His grandmother died. His uncle died. His aunt died.

Yet Alex refused to think like a victim. When he was just twelve years old, he wrote to his friend Edward Stevens (or “Neddy”), declaring:

My Ambition is [so] prevalent that I contemn the grov’ling and condition of a Clerk . . . to which my Fortune condemns me and would willingly risk my life tho’ not my Character to exalt my Station.

He ends the letter on one of history’s great non sequiturs: “I shall conclude saying I wish there was a war.”

It’s Hamilton’s oldest surviving letter. Even as a child he burned with a desire to do whatever it takes--work harder, get smarter, prove valor on a battlefield--to improve himself . . . so long as it did not compromise his honor.

There’s one more lesson here. The letter contains another, trickier, more archaic passage that isn’t quoted as often:

I’m confident, Ned that my youth excludes me from any hopes of immediate preferment nor do I desire it, but I mean to prepare the way for futurity . . . My folly makes me ashamed and [I] beg you’ll conceal it, yet Neddy we have seen such schemes successful when the Projector is constant.

Okay, some real talk: On the first read, that paragraph is nearly incomprehensible. Yet it contains the keys to Hamilton’s playbook. Douglas Hamilton (the fifth great-grandson) thinks of this advice all the time, he lives by it, and he shares it with his grandchildren, who are often baffled. “People ask me, Projector? What the hell does that even mean?” 

Let’s look at the sentence again: 

. . . we have seen such schemes successful when the Projector is constant . . .

 The Projector is the thing that is projecting an outcome, the thing doing the work. You. If the projector is constant--with steady work--then you can prepare yourself for a better future. This is how you rise above your station. 

He had no parents, no inheritance, no formal education, and no obvious path to success. Yet he knew it was possible. He believed. From the very beginning, it would always be Alexander Hamilton against the world.

That’s a fair fight.

Steal (New Skills) from Every Job 

“[A childhood job in a trading shop was] the most useful part of [my] education.’ ”

Think back to your first job. Maybe it was delivering pizzas, waiting tables, or sacking groceries. Hamilton had a job like that. When his mom was still alive he helped her run a shop below their home, and then, when still a kid (possibly as young as eight), he worked at a trading shop called Beekman and Cruger. It’s the kind of job that most kids hate. He must have swept the floors, wiped the counters, and spent hours tediously double-checking the inventory.

Yet the job offered something more. For perhaps the first time in his life, Hamilton began to glimpse a larger world. Some quick context: When people say that Hamilton was from “a forgotten spot” or “the middle of nowhere,” that’s not entirely true. Every morning, as a fleet of ships hugged the wharfs of St. Croix, he woke up to a bustling commercial hub. Sugar was to the Caribbean what oil now is to the Middle East. The “white gold” could make or break empires. (How valuable was the Caribbean? In the treaty of 1763, after a military defeat, France was forced to give Britain either most of Canada or the tiny islands of Martinique, Guadeloupe, and St. Lucia. They thought about it for maybe five seconds. Then they kissed Canada goodbye.)

Hamilton saw all of the wheeling and dealing. Since the shop traded with all parts of the globe, it forced him to learn about things like foreign exchange rates and currency fluctuations--French livres, German marks, Danish kroner. He learned bookkeeping. Inventory control. When cargo sailed to the docks of St. Croix, young Hamilton unloaded the goods and lugged them to a Scale House, where he measured the lumber, pork, fish, rope, cattle, and corn. (The Scale House still exists. And it’s only a Frisbee toss away from where his mother was once imprisoned, which means he saw the jail every day.) He did his chores well. So his boss, the Dickensian-named Nicholas Cruger, soon gave him more clout: Alex would decide where the cargo should be sold, when to sell it, and how much it should cost.

“The when to sell sounds obvious, but it’s not always,” explains historian Michael E. Newton. Hamilton once inspected a boatload of scrawny mules. “A...