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…