Sears Holdings' bankruptcy

Sears had been a dominant force in American retail for most of the 20th century, pioneering the mail-order catalog and later the suburban department store, but it struggled for decades to adapt as discount chains, then Walmart and eventually online retailers like Amazon undercut it on price and convenience. Hedge-fund manager Eddie Lampert took control of the company after engineering its 2005 merger with Kmart, and over the following years pursued a strategy of cutting costs and spinning off valuable real estate and brands into separate entities, even as he personally became the company's largest creditor through his hedge fund's loans to it — a structure critics said benefited Lampert at the expense of the retailer's survival. Sears Holdings filed for Chapter 11 bankruptcy protection on October 15, 2018, listing roughly $11.3 billion in debt against about $7 billion in assets, after years of store closures had already shrunk the chain from more than 3,500 stores to under 700. Lampert's hedge fund ultimately bought the remaining stores out of bankruptcy in 2019, keeping a small footprint of Sears and Kmart locations operating.