CTRL+Z: Rewritten

Mikhail Gorbachev hits CTRL+Z

CTRL+Z: Rewritten

Show Notes

In 1991, the men around Mikhail Gorbachev spent two years begging him to send in the army and hold the Soviet Union together. He had already ordered three crackdowns that left unarmed civilians dead, but when it came time to crush the republics for good, he refused. By the end of that year the largest empire on earth had dissolved, and in Russia they have cursed his name ever since.

It almost went the other way. The crackdown his hardliners wanted had been on the table the entire time, and the only real questions were who would give the order and whether the soldiers would obey. Across the same years, the other great communist power made the move Gorbachev wouldn't, sending its tanks into Tiananmen Square, and it's still standing today, richer and stronger than the Soviet Union ever was.

What if Gorbachev had given the order himself?

This week we hit Control Z on the order Gorbachev refused to give, follow the surviving Soviet Union all the way to 2026, and find the lesson underneath: the choice his own country can't forgive is the one that ended the Cold War and set Eastern Europe free.

More from CTRL+Z: Rewritten

Oct 17, 2026

On Thursday, August 21st, 2008, Joe Biden sat in a dentist’s office while his wife had a root canal, and Barack Obama was choosing his running mate. For 2 months Obama had kept Hillary Clinton on his list, though his campaign manager and chief strategist wanted her off it. She had the smarts, discipline, and steadfastness he wanted, he told them, but Bill Clinton was a complication. If he picked her, he said, there would be more than 2 of us in the relationship. By December the former president had agreed to 9 rules on his foundation’s money so his wife could run the State Department. He had 2 choices. Call Biden at the dentist’s office, or offer the job to Clinton. He called Biden, who said yes. Clinton used a private email server as secretary of state, and the FBI director wrote Congress about it 11 days before she lost Michigan, Wisconsin, and Pennsylvania. Biden took the oath as the 46th president in January of 2021. What if he’d offered it to Clinton? This week we hit CTRL+Z on the call to the dentist’s office, and follow the ripple to today: Bill Clinton holding the Bible while Justice Ruth Bader Ginsburg swears in his wife as vice president, Secretary of State John Kerry receiving the coffins from Benghazi, a woman’s victory speech under the glass ceiling of the Javits Center, Donald Trump convicted by a Manhattan jury as his own TV channel covers the trial, and children taking class in tents on high school football fields in the fall of 2020. In 2026 Marco Rubio is the 46th president, Joe Biden is retired in Wilmington, and every public school built with federal money has a classroom outside, because one Thursday in August the call went to the Clintons’ house in Chappaqua.

Oct 10, 2026

On January 2nd, 1492, Ferdinand and Isabella took the surrender of Granada, and a 40-year-old sailor from Genoa watched from the crowd. For 6 years Christopher Columbus had asked them to pay for a voyage west to Asia, and twice their experts had told them the ocean was too wide. Within days they turned him down again, this time over his price: admiral, viceroy, and a tenth of the profit. He packed his charts on a mule and rode for France. Back in the camp, the king’s finance officer told the queen the whole fleet needed only 2,500 crowns, about a quarter of 1 percent of what the war had cost, and offered to lend it himself. She had 2 choices. Let him go, or send someone after him. She sent a court officer, who caught Columbus on a stone bridge 4 miles down the road. The contract was signed April 17th, 3 ships left Palos in August, and on October 12th a lookout sighted land in the Bahamas. What if she’d let him go? This week we hit CTRL+Z on the bridge at Pinos, and follow the ripple to today: a Genoese chartmaker growing old in a room over the harbor at Honfleur with Japan drawn 2,400 miles west of the Canaries, a Portuguese clerk writing Lisbon a letter about parrots from a beach in Brazil, a Breton captain named Jacques Cartier anchoring off Hispaniola in 1534, a grandson of Moctezuma ruling a city that buys its matchlocks from Norman traders, and a Spanish army marching out of the Netherlands because the king can’t pay it. In 2026 the 2 continents are called Santa Cruz, Portuguese is spoken from the Amazon to the River Plate, and Tenochtitlan is still on its lake, because one January a queen let a sailor keep riding.

Oct 4, 2026

Unfortunately, I came down with an illness this week that took my voice completely. So, instead of nothing, I'm sharing one of my favorite episodes to research:

Sep 27, 2026

On Easter Sunday, April 10th, 1803, Napoleon Bonaparte sat inside the palace of Saint-Cloud with 2 ministers who couldn't agree. One told him to sell the French colony of Louisiana before the Royal Navy took it for nothing. The other told him to keep it and send the 12 ships and 3,000 soldiers already waiting in a Dutch harbor. Britain was 38 days from declaring war, and an American named James Monroe was already riding for Paris with orders to buy one city, New Orleans, for 10 million dollars. He had 2 choices. Sign the order that sent the fleet, or sign the order that gave the whole territory away. At daybreak he told his treasury minister, "I renounce Louisiana." The United States paid 15 million dollars and nearly doubled in size. Britain declared war 18 days later. What if he'd listened to the other minister? This week we hit CTRL+Z on the palace at Saint-Cloud, and follow the ripple to today: a French garrison dying of yellow fever behind an earthen wall on the Chalmette plain, a British admiral landing troops through a Louisiana bayou 11 years before Andrew Jackson tries to take the same ground and fails, a Cherokee chief signing for land on the Arkansas river under the protection of the Crown, and a Canadian prime minister promising a railway from Montreal to New Orleans. In 2026 the Mississippi river is an international border for its entire length, and the customs post on the Memphis bridge flies a foreign flag, because one Easter Sunday a First Consul changed his mind by morning.

Sep 26, 2026

Just a quick update as to why there was no episode today and informing you that Episode 28 comes out tomorrow!

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