The Big Question

What is the greatest upset in history?

Graham Roumieu

James T. Campbell, history professor, Stanford

Arthur Ashe’s defeat of a seemingly invincible Jimmy Connors in the 1975 Wimbledon final. The qualities of character Ashe displayed—grit and guile, patience and deflection, gentleness alloyed with fierce self-belief—were precisely those that had enabled him and millions of others to endure and ultimately transcend the serial assaults of Jim Crow.

Linda Greenhouse, lecturer, Yale Law School

The collapse of the Soviet bloc. The disappearance of the U.S.S.R. and its empire ushered in a complex and perhaps no less frightening world, but to anyone who grew up during the “duck and cover” height of the Cold War, it remains an amazing event—if not the biggest upset in history, then at least in the lifetime of those still on this planet.

Chris Berman, ESPN commentator

The night Chaminade University beat Virginia in college basketball. It was 1982, and I was on SportsCenter with Tom Mees when the message came across the wire. We said, “We can’t go with this—this is a mistake!” But then someone ran out with a piece of paper: “Resending, correct: Chaminade 77, Virginia 72.” With one minute left, we said, “We can’t tell you what happened, but the No. 1 team in college basketball has lost to—we don’t even know who they are.”

Nina Totenberg, legal-affairs correspondent, NPR

The famous 1948 headline is “Dewey Defeats Truman.” Truman’s election victory was so unexpected, so unpredicted by polls or pundits, that the president held the errant newspaper over his head the day after the election. That says it all.

James M. McPherson, author, Battle Cry of Freedom

Harry Truman’s victory over Thomas Dewey in the presidential election of 1948. Nearly everyone had predicted a Dewey victory, and the Chicago Tribune famously misreported his triumph in its early edition. I was 12 years old, and knew Dewey would win, because my parents and grandparents said he would. I still remember the egg on their faces.

Cass Sunstein, legal scholar

The rise of Christianity. Two thousand fifteen years ago (give or take), Jesus Christ was crucified. Whether or not you think that he was the son of God, no oddsmaker would have predicted that today the faith of billions would bear his name.

J. R. Moehringer, novelist and journalist

How could it not be the Battle of Thermopylae? For a few days in 480B.C., 300 Spartans held off the entire Persian army, which was set to conquer the world. Though allwere killed, they won what Montaigne called a triumphant defeat, slowing the Persian onslaught and inspiring Greece to ultimate victory. If not for Thermopylae: no Socrates, no Plato, no Aristotle, no democracy, no Western civilization.

Jon Wertheim, executive editor and senior writer, Sports Illustrated

The food truck. Those pedigreed chefs and their molecular gastronomy? Concept restaurants with pairing menus? They’ve been supplanted in the food revolution by the plucky upstarts, the fleet of vehicular kitchens now ubiquitous in every city. No seating? The chef doubles as cashier? Who cares? We love our $6 burritos and bento boxes. Runner-up: Buster Douglas defeating Mike Tyson.

Eric Foner, historian

The abolition of slavery in the United States. On the eve of the Civil War, slavery was the most powerful economic institution in the country, worth more than the banks, factories, and railroads put together. Slaveholders had dominated the federal government since its creation. No one anticipated emancipation anytime soon. This is why Lincoln, shortly before his death, called the end of slavery “astounding.”

Patton Oswalt, comedian and author, Silver Screen Fiend

Mammals winning out over the dinosaurs. Whatever upset the balance—asteroid, climate change, clumsy time travelers—gave us the space to climb down from the trees and take over the planet. I wouldn’t have bet on our ancestors against the thunder lizards, but here I sit, typing on my laptop, which I’m now going to use to look at porn. Thank God our side won, huh?

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