On March 6, 1995, WIRED’s executive editor and resident techno-optimist Kevin Kelly went to the Greenwich Village apartment of the author Kirkpatrick Sale. Kelly had asked Sale for an interview. But he planned an ambush.

Kelly had just read an early copy of Sale’s upcoming book, called Rebels Against the Future. It told the story of the 19th-century Luddites, a movement of workers opposed to the machinery of the Industrial Revolution. Before their rebellion was squashed and their leaders hanged, they literally destroyed some of the mechanized looms that, they believed, reduced them to cogs in a dehumanizing engine of mass production.

Sale adored the Luddites. In early 1995, Amazon was less than a year old, Apple was in the doldrums, Microsoft had yet to launch Windows 95, and almost no one had a mobile phone. But Sale, who for years had been churning out books complaining about modernity and urging a return to a subsistence economy, felt that computer technology would make life worse for humans. Sale had even channeled the Luddites at a January event in New York City where he attacked an IBM PC with a 10-pound sledgehammer. It took him two blows to vanquish the object, after which he took a bow and sat down, deeply satisfied.

Kelly hated Sale’s book. His reaction went beyond mere disagreement; Sale’s thesis insulted his sense of the world. So he showed up at Sale’s door not just in search of a verbal brawl but with a plan to expose what he saw as the wrongheadedness of Sale’s ideas. Kelly set up his tape recorder on a table while Sale sat behind his desk.

The visit was all business, Sale recalls. “No eats, no coffee, no particular camaraderie,” he says. Sale had prepped for the interview by reading a few issues of WIRED—he’d never heard of it before Kelly contacted him—and he expected a tough interview. He later described it as downright “hostile, no pretense of objective journalism.” (Kelly later called it adversarial, “because he was an adversary, and he probably viewed me the same way.”) They argued about the Amish, whether printing presses denuded forests, and the impact of technology on work. Sale believed it stole decent labor from people. Kelly replied that technology helped us make new things we couldn’t make any other way. “I regard that as trivial,” Sale said.

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 this 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. As the time to settle approached, both men agreed that Patrick, the holder of the checks, should determine the winner on December 31. Much more than a thousand bucks was at stake: The bet was a showdown between two fiercely opposed views on the nature of progress. In a time of climate crisis, a pandemic, and predatory capitalism, is optimism about humanity’s future still justified? Kelly and Sale each represent an extreme side of the divide. For the men involved, the bet’s outcome would be a personal validation—or repudiation—of their lifelong quests.

Sale’s provocative book, Rebels Against the Future, is just one title in a shelf-full of works urging a return to a preindustrial life. His fervor for the simple life took root early. John Kirkpatrick Sale grew up in a close-knit suburb of Ithaca, New York, one of three sons of William F. Sale Jr., who taught literature at Cornell. Sale père was a legend in the field; his students included Kurt Vonnegut and Harold Bloom. Kirkpatrick Sale felt that his tiny community was idyllic. When a plan was proposed to merge his local school into the Ithaca district, young Sale spoke out against it. “Something in my genes flatly resisted the idea of leaving a human-scale school for the vagaries of education down in the city of Ithaca,” he later wrote. (Ithaca at the time had all of 30,000 inhabitants.)

Kirkpatrick attended Cornell, the family institution. He studied history, but with an eye toward journalism. Even then he was a rebel. In the late 1950s, there was no war to protest against, but there was a policy called in loco parentis, which put school administrators in charge of moral probity. Sale, who was the former editor of the student newspaper, was enraged by a proposal to ban unchaperoned coeds from off-campus parties. He helped incite close to 1,500 people to demonstrate. In the hubbub, the dean of men got hit by an egg, and protesters hurled rocks and smoke bombs at the beleaguered university president. Sale was suspended, as was his roommate, novelist-to-be Richard Fariña.

Even back then, Sale distrusted computers. With another classmate, he cowrote a sci-fi musical about escaping a dystopian America ruled by IBM; it features an evil computer. If this sounds at all Pynchonesque, it’s probably because Sale’s cowriter was Thomas Pynchon. Nonetheless, a line in it foreshadows Sale’s later work. “All we want is someplace where every time we turn around we don’t see that idiot damn machine staring at us,” one character gripes. This is 1958.

After college, Sale worked for a leftish publication and spent time in Africa. Returning to the US as the counterculture was gaining steam, he became fascinated with the pivotal antiwar group Students for a Democratic Society, and he wrote the definitive book on the organization. He later said that the immersion “radicalized me in a way beyond where I’d been.”

During the ’70s, he began formulating a philosophy that took cues from the budding environmental movement. “I was at the dining table one morning thinking about the human scale in architecture, and how modern architecture had completely lost it,” he says. It got him thinking more broadly about the shortfalls of city planning, and then of how nations are organized. He realized he had always been, as he puts it now, an “anarchocommunalist.” With thoughts of the convivial village of his childhood in mind, Sale began advocating for decentralized, self-sufficient systems—with life organized at “human scale,” which became the title of a book-length manifesto. One of his treasures was a collection of books that once belonged to E. F. Schumacher, the author of Small is Beautiful.

Sale’s work intertwines two threads: bitter condemnation of so-called progressive civilization and idyllic blueprints for a stripped-down life. For the 500th anniversary of Columbus’ landing, he wrote a book bemoaning the ruination of North America. The title said it all: The Conquest of Paradise. In another book, After Eden, he postulated that everything began going downhill when humans started hunting large game, kicking off a relentless trend of destroying the natural world. He often finds himself defending Paleolithic societies; his outrage at the term “cavemen” surpasses even the indignation of the hirsute figure in the Geico commercial.

While none of Sale’s own tomes became runaway best sellers, he says that some of them made back their considerable advances. “They were talked about even when disagreed with,” he says. For many years, he was a fixture on the lecture circuit, and he estimates he visited at least 250 college campuses.

And then came the Rebels book. His take on the Luddite story provided a novel counterpoint to the media’s swooning over the nascent internet, and Sale had a pop culture moment. (I wrote about the book myself in Newsweek.) In its pages, Sale aired out the civilization collapse theory that he’d been developing for years. “If the edifice of industrial civilization does not eventually crumble as a result of a determined resistance within its very walls, it seems certain to crumble of its own accumulated excesses and instabilities within not more than a few decades, perhaps sooner,” he wrote.

Sale’s Cassandra-like warning got less attention than the stunt he used to promote it. “I had TV people from all over the world come to me, often with their own used computers so I’d have something to hit,” he says. He readily complied. But that was not his usual MO. “Kirk was always somewhat aloof, in a grand sort of way,” his former editor Bill Patrick says. “Just a bit aristocratic—academic, the stodgy English professor as opposed to the wild and crazy drama teacher.”

Despite all the smashed machinery, the Luddite book was also not a best seller, according to Patrick. But one copy, circulated in advance of its June publication, ended up on the San Francisco desk of WIRED’s executive editor, Kevin Kelly.

At the time, WIRED was two years old. Kelly had been a key player in its origin, urging founders Louis Rossetto and Jane Metcalfe to move to San Francisco to launch it. Under Kelly’s leadership, it became a flagship not only of the new wave of tech and internet but of a techno-optimistic way of thinking: Hackers and entrepreneurs would solve our problems.

Kelly had come to the post through a nontraditional path. Growing up in a New Jersey bedroom community, Kelly seldom traveled. But in his freshman, and only, year at the University of Rhode Island, he read books that convinced him he’d find a better education on the road. He was also inspired by the do-it-yourself ethos of the Whole Earth Catalog, the legendary 1960s book of tools for hippie agrarianism. He decided to tour Asia, indulging his passion for photography by capturing images of the most remote spots he could find.

The journey, lasting for the better part of a decade, transformed him. “I was in very remote parts of Asia, parts which were literally medieval societies in every respect, from the dress, architecture, beliefs, behavior,” he says. “I saw completely vehicle-less cities—people throwing garbage in the streets, no toilets. That’s not even to mention the hinterland villages, which were without even metal.” When he returned to the US in 1979, he had a deep appreciation for the technology that made life easier.

Kelly got a job in a biology lab at the University of Georgia and, on the side, began writing about his views and his travels. He became a computer enthusiast when he discovered that his Apple IIe could connect him with fascinating communities. He stumbled on the Electronic Information Exchange System, an early online conferencing system, and through it he got to know Stewart Brand, founder of the Whole Earth Catalog. Impressed with Kelly’s writing, Brand offered him a job editing the in-house magazine, Co-Evolution Quarterly, which was still devoted to the tools-for-living ethos of the original catalog. Later, Kelly merged the tree-hugging magazine with another Brand publication covering software and called it the Whole Earth Review. “All the organic farmers were completely outraged that we were now having reviews of software in their magazine,” Kelly says. He would tell them, You don’t understand, this is the next big thing. Just like plows and gro-lights and fertilizer, software was a tool. They all belonged on a continuum of technology that lifts our existence out of the difficult conditions he saw farmers coping with in his travels. “I got to experience the world without technology,” he says. “So when people were talking about kind of getting rid of technology, I was like, no, no, no, you have no idea.”

And that’s why Kelly found the ending chapters of Rebels Against the Future so offensive. Kelly had no problem with critiques of technology. He had once edited an issue of the Whole Earth Review headlined “Computers As Poison,” and even WIRED deviated on occasion from its ’90s-era optimism to call out the tech world’s flaws and foibles. But Sale’s rhapsodic embrace of what he called “human scale” attacked progress. In his travels, Kelly also had seen how modern industry and tech could improve lives. Sometimes he liked to return to the remote villages he had visited in his youth. He saw a factory pop up where a rice paddy had been, and the villagers who had been barefoot on his first visit were now wearing sandals. As industry grew in the cities, people eagerly abandoned their human-scale existence for something different.

“They’re leaving villages that have organic food and beautiful scenery, and beautiful architecture and very strong families,” Kelly says. “Why do they do that? Because they have choices. They don’t have to be what their father or mother was, which was basically a farmer or housewife. They could maybe be a mathematician, maybe they could be a ballerina.” (Government policy may have made migration less of a choice.)

As he stewed over Sale’s message, a thought bubbled up. When Kelly gets a fresh idea, his impulse is to say, “Let’s do it!” He had read about the history of bets in science—one in particular was Julian Simon’s 1980 challenge to biologist Paul Erlich’s claim of impending resource scarcity—and liked the idea of intellectual opponents taking a public stand. “I didn’t know what we were going to bet about,” Kelly says. “I wanted him to be accountable for that romantic nonsense that he was spouting.”

Sale didn’t see things that way. “I knew the whole thing was a setup,” he says. Despite feeling conned, Sale never considered just tossing Kelly out. “We were professionals,” he says.

For more than two decades, the two bettors didn’t speak. But as the deadline drew near, Kelly set out to contact Sale. “He kind of fell off the map,” Kelly says. When Kelly eventually reached him by email, Sale was surprised to hear from his old adversary.

Sale had not forgotten the bet. He’d mentioned it in various interviews, as if recounting an amusing anecdote. But until it came due, he hadn’t reflected much on it. “It had nothing to do with my journey,” he says. When someone told him there was a website of Long Bets where people could make their own side bets on his wager with Kelly, Sale shrugged it off, befuddled.

Over the past 25 years, Sale had continued to write about decentralization and simplicity. But he had a harder time getting published. He had been unable to sell the major houses on a jeremiad against tourism, another attack on computers, or his takedown of the Emancipation Proclamation, which he self-published in 2012, arguing that Lincoln did Black people no favor by freeing them without a means to gain equality. He also became enamored of the breakup of the US as a way to achieve his small-town-bordering-on-tribal way of life.

In the mid-2000s, Sale cofounded the Middlebury Institute to promote the idea of secession. If states peeled off from the union, the theory went, Sale’s decentralized vision might get a little closer to reality. He was disappointed that the movement did not gain steam when George W. Bush was reelected. His romance with decentralization even led him to a blinkered view of the Confederacy, which he lauded for its commitment to concentrating power locally. (Sale told The New York Times he would personally prefer to live in the independent state of Hudsonia, a territory that would include New York City and the Hudson River Valley.)

Sale remained convinced that civilization was doomed. Years earlier he had advised his two daughters not to have children; they ignored him. Now he had an adult granddaughter to whom he’d one day likely offer the same advice. “She’ll probably ignore me too,” he told an interviewer this year.

So Kelly should not have been surprised at what Sale had to say in March 2019, on their first contact in decades. Collapse is coming, he said. Then Sale shared the news that he was writing a book about the bet.

The book is called The Collapse of 2020—and yes, the neo-Luddite’s latest work is available on Kindle. In fact, Sale has made compromises with technology. He recently moved back to Ithaca with his wife to be near family. He does have a computer, as well as a printer, a land line, a stove, two televisions, and four radios. He draws the line at microwaves and smartphones. Despite believing that social media has “a visible deleterious effect,” he has a public Facebook page.

In May 2020, Sale and Kelly settled on the terms of the decision. Their editor, Bill Patrick, would name the winner. Kelly proposed that Patrick wait until the last day of the year to issue his verdict, giving civilization every possible chance to self-destruct. Kelly wrote up a four-page essay to press his case. Sale suggested that Patrick read his book. But Patrick had free reign in making the determination.

When Sale and Kelly made the bet, they had assumed that by 2020 the winner would be obvious. Maybe all it would take was a look around: Is civilization still here, or not? It clearly is still kicking around. But the pandemic, its economic consequences, and the worsening climate crisis have made things interesting. What would Patrick say?

Bill Patrick lives outside of Boston, editing, ghostwriting, and book-doctoring on a freelance basis. He’s long since left his old job at the textbook publisher where he’d gotten to know Kelly and Sale. But when Kelly asked him if he still had the checks from the 25-year-old bet, he knew just where to look. He pulled open a file cabinet in his home office, flipped to a manila folder, and there were the two checks, preserved in a ziploc bag.

Patrick has his own views on technology. “I’m from the ’60s,” he says. “When computers came along, I did not view them as the next wave of liberation.” He appreciates the beauty of engineering but disdains what he feels is the arrogance of technology people. “And now the evils are very apparent,” he says. He is not on Facebook and uses a simple cell phone, not a smartphone.

In assessing the bet, he is taking a judicial stance, viewing his role more as a critical reader of the two men’s arguments than as an assessor of the world. “I am not an oracle,” he says. “I’m just me.” He decided to stick to the terms Sale had suggested on the fly on March 6, 1995. Even if it wasn’t quite fair to Sale. Patrick had a lot of sympathy for his point of view, but he felt that Sale’s extremism hurt his cause. “I wish Kirk had taken more time to become a better informed critic,” he says, adding that his broad dismissal of technology left him out of touch with reality. More relevant to the bet, though, was the way Sale had rashly agreed to terms that made victory contingent on worst-case scenarios. “Kirk was naive to accept on the spot,” he says.

Sale says that, even in retrospect, he couldn’t have come up with a better answer. “I said ‘collapse’ at dinner parties, but no one ever asked me to be specific,” he says. Moreover, Sales’ Collapse of 2020 book, which came out last January, includes an untimely concession. The very fact that his book exists, he wrote, is the equivalent of tossing his cards face down on the table: If society had in fact collapsed, there would be no books, self-published or not. “So let me just admit that I was wrong,” he wrote. “But … not by much. And not totally.” Yet shortly after the book appeared, global events seemed to tilt in Sale’s favor. The pandemic’s effect on physical and economic health, Donald Trump’s destabilization of democracy, and ever more extreme weather nudged civilization closer to the precipice. Could it be that while we haven’t retreated to caves and hovels, Sale’s predictions have landed in the ballpark of reality?

That’s what Patrick had to determine. In early December he began writing up his decision. Despite his wariness toward tech, he had no intention of jumping on the current techlash bandwagon. Instead, the bet was constructed on three clear conditions, and Patrick would consider each one separately, as if judging a boxing match round by round.

Economic Collapse. Sale predicted flatly that the dollar and other accepted currencies would be worthless in 2020. Patrick points to the Dow at 30,000 and the success of new currencies such as Bitcoin. “Not much contest here,” Patrick writes. Round goes to Kelly.

Global Environmental Disaster. Kelly tried to argue that despite worsening climate change, people are still living their lives pretty much as usual. “If this is a disaster, that is not evident to Earth’s 7 billion inhabitants,” Kelly wrote in his four-page argument. But Patrick isn’t convinced. “With fires, floods, and rising seas displacing populations; bugs and diseases heading north; ice caps melting and polar bears with no place to go; as well as the worst hurricane season and the warmest year on record, it’s hard to dispute that we are at least ‘close to’ global environmental disaster,” Patrick wrote in his final decision. This one is Sale’s.

The War Between Rich and Poor. Sale’s book cites devastating statistics on income inequality and the frayed social fabric. If he had written his book after the pandemic, the picture would be even worse. But are the classes at war? Patrick notes that in the decades since Kelly and Sale made the bet, breathtaking economic development has reshaped China and India, among other countries. On the other hand, he points to undeniable social unrest, even in the United States, with Trumpites taking to the streets with semiautomatic weapons, and massive protests against police abuses. He calls this round a toss-up, with an edge to Sale.

Round by round, the outcome would seem to make it a draw. But when making the final call, Patrick stuck to the language of the original bet. In that fateful Greenwich Village encounter, Sale called for a convergence of three disasters. “Kirk must hit the trifecta to win, meaning that all three horses of his apocalypse must come through,” Patrick wrote. “Only one of his predictions was a winner; one came in neck and neck; and one was way back in the pack.”

So on December 31, Patrick declared Kelly the winner in an email to the bettors. “But it’s a squeaker and not much cause for celebration,” he concluded.

It’s also not terribly satisfying. Because Kelly’s upbeat views seem to have crossed the finish line as Sale’s apocalyptic horsemen were closing fast, 2020 offered no clear verdict as to civilization’s fate—or where we will be in the next 25 years.

That’s due both to the extraordinariness of 2020 and to the bettors’ own limitations. They staked out extreme positions in a world that’s always likely to regress to the mean. Sale failed to account for how human ingenuity would keep us from getting tossed into forests and caves. Kelly didn’t factor in tech companies’ reckless use of power or their shortcomings in solving (or sometimes stoking) tough societal problems.

They’re also as entrenched as ever. Despite this miserable year, Kelly is boosting his optimism to a higher gear. With tech’s help, he believes, the world’s woes will be resolved. “In 25 years, poverty will be rare, and middle-class lifestyle the norm,” he wrote in his submission to Patrick. “War between nations will also be rare. A bulk of our energy will be renewables, slowing down climate warming. Life spans continue to lengthen.” He’s working on a book he calls Protopia.

Sale believes more than ever that society is basically crumbling—the process is just not far enough along to drive us from apartment blocks to huts. The collapse, he says, is “not like a building imploding and falling down, but like a slow avalanche that destroys and kills everything in its path, until it finally buries the whole village forever.”

Kelly wrote to Sale on New Year’s Day, instructing him to direct the $1,000 to Heifer International, a nonprofit that gives away breeding pairs of animals. Sale puzzled him by replying, “I didn’t lose the bet.” Kelly assumed he hadn’t seen Patrick’s decision, and he had the editor resend it.

But Sale had read it—and rejected it.

“I cannot accept that I lost,” he wrote to Patrick. “The clear trajectory of disasters shows that the world is much closer to my prediction. So clearly it cannot be said that Kevin won.”

Like the raging denialist in the White House, the cantankerous anarchocommunalist has quit the game after the final score left him short. Sale says he is seeking some sort of appellate relief, if only by public opinion, when in fact the rules included no such reconsideration. Kelly is infuriated. “This was a gentleman’s bet, and he can only be classified as a cad,” he says. Kelly warns Sale that history will recall him as a man who doesn’t honor his word. But Sale doesn’t believe that there will be a history. For Kirkpatrick Sale, collapse is now, and all bets are off.

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