Part 7: The Early 20th Century: Teddy’s Swagger and Hoover’s Crash (1900s–1930s)

As the 20th century cracks open, America stumbles out of the Gilded Age with all the dignity of a frat boy waking up on a stranger’s lawn. The population explodes—76 million by 1900—fed by immigrants pouring off ships in droves, lured by a promised paradise that’s mostly propaganda. The nation’s industrial furnace blazes, belching steel and bravado faster than Europe can figure out what hit it. The Civil War is ancient history, the frontier is a pile of bones, and the U.S. is hellbent on proving it can throw elbows on the global playground.

It kicks off dramatically enough with an explosion: the USS Maine goes up in flames in Havana harbor in 1898, a mystery the yellow press blames on Spain with all the subtlety of a Fox News chyron. Cue the Spanish-American War—a ten-week smash-and-grab dressed in patriotic drag. Teddy Roosevelt, all swagger and mustache, charges up San Juan Hill, and within months, America snatches Puerto Rico, Guam, and the Philippines. Cuba gets a sham “independence” with Uncle Sam’s strings attached, while the Philippines endures a bloody guerrilla war, politely termed “benevolent assimilation,” resulting in 200,000 Filipino casualties—an early American demonstration that “liberation” usually means someone else’s funeral.

Roosevelt rides that imperial bravado into the White House by 1901, where he turns his manic energy inward, busting monopolies and reluctantly signing laws after Upton Sinclair’s nauseating exposé, The Jungle, makes everyone afraid of their lunch. Sure, trusts get slapped and meat inspection becomes a thing, but robber barons still clink champagne glasses, workers still lose limbs in factories, and America’s progressive makeover mostly glosses over the grime rather than scrubbing it clean.

When Europe decides to self-destruct in 1914, America plays it smart at first—selling weapons and food to anyone with a wallet, while President Woodrow Wilson preaches lofty neutrality. But German U-boats torpedo U.S. ships, and by 1917, Wilson flips from preacher to war hawk, tossing 2 million doughboys into Europe’s blood-soaked trenches. The Allies win by 1918, at the price of 116,000 American lives and countless shattered psyches. Wilson swaggers into Versailles pitching his League of Nations, an idealistic scheme doomed by America’s allergic reaction to global cooperation—Congress sneers, rejects it, and the nation retreats into isolationist sulking.

The Roaring Twenties stumble in, drunk on bathtub gin and jazz, with Wall Street peddling the fantasy of infinite riches. Flappers dance, speakeasies boom, and stocks inflate like birthday balloons—until the music abruptly stops in October 1929. The market crash vaporizes $30 billion overnight, banks collapse, and the Great Depression arrives like an unwanted relative who won’t leave. By 1933, a quarter of the workforce stands idle, breadlines stretch around city blocks, and shantytowns sarcastically named “Hoovervilles” mock President Herbert Hoover’s pathetic response of “rugged individualism”—code for “you’re on your own, bitch.”

Nature piles on with Dust Bowl storms choking the Great Plains, sending desperate Okies streaming west with nothing but empty pockets and fading dreams. Enter Franklin Roosevelt in 1933, flashing his New Deal smile and tossing lifelines—jobs, dams, Social Security—to a drowning nation. It’s relief, not revolution; minorities and sharecroppers still get stiffed, Jim Crow still rules the South, but at least someone’s pretending to care. Banks reopen, factories sputter back to life, and capitalism lives to screw another day.

Imperialism, idealism, innovation and greed. America learns it can bully globally, get rich off bloodshed, and blow the winnings in a heartbeat. Teddy’s bravado, Wilson’s naïve dreams, and Wall Street’s reckless binge are more proof America could punch above its weight, fall flat on its face, and still dust itself off with a cocky grin and a wink.