Part 2: Pilgrims, Puritans, and the Art of Ruining a Good Thing (1600s–1700s)

If Columbus was the guy who crashed the party, the early English settlers were the dickhead buddies he texted the address to really ruin things. These weren’t the noble pioneers of your school play; they were a mix of greedy chancers, religious nutjobs, and suckers who thought a boat ride could fix their problems. Starting in the early 1600s, they stumble across the Atlantic—first to Jamestown, then Plymouth, then Massachusetts Bay—each group proving that a fresh start doesn’t mean a clean slate, just a new place to fuck up. What they build is less a shining beacon than a flickering neon sign reading “Plunder N Pillage.”

First up is Jamestown, the Virginia Company’s 1607 get-rich-quick scheme that lands 104 men and boys on a swampy hellhole in what’s now Virginia. These aren’t rugged survivalists; they’re a ragtag crew of “gentlemen”—code for lazy aristocrats who think digging is beneath them—plus some laborers and a dream of gold that’s about as realistic as a unicorn ranch. They pick a spot with brackish water, malaria-ridden mosquitoes, and no food, because apparently “planning” was too much of a pain in the ass. The Powhatan, the local confederacy led by Chief Wahunsenacawh (aka Powhatan), watch these idiots starve and bicker, probably wondering if they’re a threat or just a funny white joke. By the first winter, two-thirds of them are dead—some from hunger, some from disease, and at least one from a musket ball to the leg in a fight over who gets the last soggy biscuit.

Enter John Smith, the pint-sized braggart who turns Jamestown into his personal action movie. He strong-arms the survivors into planting crops and trading with the Powhatan, who reluctantly toss them corn to keep them from keeling over entirely. The Pocahontas story gets trotted out here—Smith claims she saved him from execution, but it’s more likely a ritual misunderstanding he spun into a PR win. She’s 11, he’s 27, and the Disney vibes are nowhere to be found in the real story. By 1609, Smith’s back in England, and Jamestown hits the “Starving Time”—a winter so bad they’re eating rats, boots, and, yeah, each other. One guy kills his pregnant wife, salts her, and snacks on her before they catch him. The Virginia Company sends reinforcements, but it’s less a rescue and more a corporate bailout for a colony that’s less profitable than a lemonade stand in a blizzard.

The Powhatan try to coexist—trading food for tools—until the English get greedy. Tobacco saves Jamestown’s bacon in the 1610s, thanks to John Rolfe (who later marries Pocahontas, now a kidnapped convert named Rebecca), but it’s a land-hungry crop. The settlers start muscling onto Powhatan turf, and by 1622, the tribe’s had enough. They launch a raid, kill 347 colonists, and nearly wipe the place out. The English retaliate with a decade of vengeance, poisoning peace talks (literally, at one point) and shrinking the Powhatan’s world. By the 1640s, Jamestown’s a tobacco-fueled feudal state, importing African slaves in 1619 to keep the profits rolling—because why stop at screwing the natives when you can screw a whole new continent too?

Then come the pilgrims, the Mayflower weirdos who hit Plymouth in 1620, a year after Jamestown’s slave ships dock. They’re Separatists—Puritans too hardcore for other Puritans—fleeing England’s “sinful” ways for a blank canvas to paint with gloom. Half die that first winter, shivering in their piety while the Wampanoag, led by Massasoit, send Squanto to teach them corn and patience. The 1621 harvest bash—later Thanksgiving—feels like a win, but it’s a Trojan horse. More ships follow, smallpox tags along, and by the 1670s, Massasoit’s son Metacom (King Philip) is fighting a losing war. His head ends up on a pike in Plymouth, a grim holiday centerpiece for 20 years.

Up north, the Puritans proper land in Massachusetts Bay in 1630, led by John Winthrop and his “city on a hill” sermon that’s more of a threat than a theological pep talk. They’re better funded than the pilgrims, more organized than Jamestown, and twice as judgmental. Church is law, fun is sin—dancing’s out, Christmas is canceled, and witches are fair game. The 1692 Salem trials see 20 people hanged or crushed because some girls threw fits and the town lost its mind. Dissenters like Roger Williams and Anne Hutchinson get exiled—Williams to Rhode Island, Hutchinson to a grave in New York after a native raid the Puritans cheer as God’s will. The Pequot aren’t so lucky; in 1637, the English torch their village, killing hundreds, and sell the rest into slavery.

The natives—Powhatan, Wampanoag, Pequot—start strong, trading and tolerating, but end up squeezed out. By the 1700s, English numbers hit 50,000, while tribal lands shrink under deeds and diseases they didn’t sign up for. Jamestown’s a slave-powered cash cow, Plymouth’s a pious footnote, and Massachusetts is a theocratic pressure cooker. This isn’t the plucky settler saga you memorized for a Monday morning test—it’s a three-ring circus of greed, zealotry, and collateral damage, starring folks who fled oppression only to perfect it.

Meet the new world, same as the old world.