How the Richest Company in America Went Completely Broke: Sears

Henry Caldwell

Henry Caldwell

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In 1886, a railroad station agent in Minnesota sold a shipment of unwanted watches and built the largest retailer in American history. Sears, Roebuck and Company grew from a mail-order catalog business into a company that employed 350,000 people, owned the tallest building in the world, and put a Kenmore appliance in half the homes in the country. Craftsman tools, DieHard batteries, the Wish Book, Allstate Insurance, the Discover Card — all Sears. Then came the financial services gamble, the $3.9 billion loss, the death of the catalog, and a hedge fund manager named Eddie Lampert who merged Sears with Kmart and spent the next thirteen years extracting value until there was nothing left to extract. The Sears Tower is now the Willis Tower. Five stores remain. This is the full story of how it happened — from Richard Sears and Julius Rosenwald to the 2018 bankruptcy filing — told through the dollar amounts, the decisions, and the people who made them.
Sources:

Peter M. Ascoli, Julius Rosenwald: The Man Who Built Sears, Roebuck and Advanced the Cause of Black Education in the American South (Indiana University Press, 2006)
"The Rise and Fall of Sears," Smithsonian Magazine, July 2017
"Eddie Lampert Shattered Sears, Sullied His Reputation, and Lost Billions of Dollars. Or Did He?," Institutional Investor, December 2018
Sears, Roebuck and Company Complex, National Historic Landmark documentation, Library of Congress
"Sears Could've Been Amazon. Here's How It Blew Its Chances," Fortune, 2021
Willis Tower historical records, Skidmore, Owings & Merrill / Britannica