The Rise and Fall of Sears: America’s Forgotten Retail Giant

Boom and Bust

Boom and Bust

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How did Sears, once the world's largest retailer with the tallest tower, end up filing for bankruptcy in 2018?

In 1886, Richard Sears started with a simple crate of watches, eventually building a catalog empire known as the Wish Book. By 1973, the company stamped its dominance on the skyline by opening the Sears Tower in Chicago. Despite this massive success in retail history, the firm struggled to adapt as the market changed around it.

The narrative of this business failure is often simplified, but the reality involves a series of strategic distractions. While competitors focused on logistics and stores, Sears pivoted toward financial services, acquiring Dean Witter and launching the Discover Card. This video examines the full timeline from the height of the catalog era to the 2005 Kmart merger and the eventual 2018 Sears bankruptcy.

Did your family order from the Sears Wish Book? Let me know in the comments — I read every one. Subscribe to Boom and Bust — every week, the full story of how a legendary company rose, and how it fell.

0:00 The Fall of a Retail Giant
0:55 The Freight Agent's Big Idea
2:11 The Wish Book Revolution
4:22 Moving from Catalog to Concrete
9:06 Socks to Stocks: The Great Distraction
19:50 The Final Hedge Fund Chapter