Where did stores like JCPenney and Sears go wrong so they either have to file for bankruptcy or close multiple stores?

The management of these stores saddled the stores with debt, and their death knell was hastened by debt service.

In order to eliminate the debt, the companies sold assets (as stated in the other answers), and rewarded upper management for “saving” the company. Many times we see this with leveraged buyouts, where the employees purchase the company, the current management gets their “golden parachute”, and the new managers sell off the assets to keep the company alive.

Since the asset sales only service the debts, there is no money for expansion, product development, and marketing — While they flounder and fail, Amazon and more nimble businesses take their unhappy customers to newer, more customer focused operations.

Most of the people involved in these schemes have loyalty only to the dollars they can generate, and not to the long term employees, customers, or business relationships built over many years of profitable business dealings.

Not all businesses fell victim to this; The CEO of Target, Brian Cornell, pivoted as his stores serviced the internet customers who are willing to get their products with internet initiated “contactless pickups”. Targets stores are basically warehouses selling food, toothpaste, bicycles, and more. Costco has a business philosophy that keeps them profitable and works hard to ward off the short term profiteers. Home Depot Booted Bob Nardelli from the CEO spot, only to have him resurface at Chrysler; He has since moved on.

JC Penney and Sears are bellwethers of an idolized and not to distant past that needed to be changed, but took too long to adapt. Working at Sears in Massapequa, NY, helped pay my college tuition. Perhaps Lowes (the new champion of Craftsman brand tools) will revitalize the brand and their world-famous lifetime guarantee. (FYI — Craftsman is made by Stanley Black and Decker now).

I will miss the old Sears, but get 5% using my Amazon store card — and free delivery with Prime.