In 1995, a WIRED cofounder challenged a Luddite-loving doomsayer to a prescient wager on tech and civilization’s fate. Now their judge weighs in.

Sale believed society was on the verge of collapse. That wasn’t entirely bad, he argued. He hoped the few surviving humans would band together in small, tribal-style clusters. They wouldn’t be just off the grid. There would be no grid. Which was dandy, as far as Sale was concerned.

“History is full of civilizations that have collapsed, followed by people who have had other ways of living,” Sale said. “My optimism is based on the certainty that civilization will collapse.”

That was the opening Kelly had been waiting for. In the final pages of his Luddite book, Sale had predicted society would collapse “within not more than a few decades.” Kelly, who saw technology as an enriching force, believed the opposite—that society would flourish. Baiting his trap, Kelly asked just when Sale thought this might happen.

Sale was a bit taken aback—he’d never put a date on it. Finally, he blurted out 2020. It seemed like a good round number.

Kelly then asked how, in a quarter century, one might determine whether Sale was right.

Sale extemporaneously cited three factors: an economic disaster that would render the dollar worthless, causing a depression worse than the one in 1930; a rebellion of the poor against the monied; and a significant number of environmental catastrophes.

“Would you be willing to bet on your view?” Kelly asked.

“Sure,” Sale said.

Then Kelly sprung his trap. He had come to Sale’s apartment with a $1,000 check drawn on his joint account with his wife. Now he handed it to his startled interview subject. “I bet you $1,000 that in the year 2020, we’re not even close to the kind of disaster you describe,” he said.

Sale barely had $1,000 in his bank account. But he figured that if he lost, a thousand bucks would be worth much less in 2020 anyway. He agreed. Kelly suggested they both send their checks for safekeeping to William Patrick, the editor who had handled both Sale’s Luddite book and Kelly’s recent tome on robots and artificial life; Sale agreed.

“Oh, boy,” Kelly said after Sale wrote out the check. “This is easy money.”

Twenty-five years later, the once distant deadline is here. We are locked down. Income equality hasn’t been this bad since just before the Great Depression. California and Australia were on fire this year. We’re about to find out how easy that money is…

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