Sears, Roebuck and Co.

Sears was Amazon before Amazon existed. The Sears catalog, launched in 1893, delivered everything from watches to entire houses to rural America. At its peak, Sears was the largest retailer in the world, the company that built the tallest building in the world (the Sears Tower, now Willis Tower), and the employer of 350,000 Americans.

Sears had every advantage. It had the logistics network, the customer data, the brand trust, and even an early e-commerce experiment (Prodigy, in the 1980s). It should have become Amazon. Instead, it became a case study in corporate decline.

Eddie Lampert's 2005 merger of Sears and Kmart created a company optimized for extracting value, not creating it. Stores rotted. Inventory thinned. Real estate was sold off. The Kenmore, Craftsman, and DieHard brands were licensed or sold. Lampert's hedge fund collected management fees while the company burned through $12 billion in cash. Sears filed for bankruptcy in 2018. A handful of stores remain, technically open, functionally dead.