Sears Holdings, the parent company of Sears and Kmart, faces an October 15 deadline to pay $134 million on its debt. CEO and primary shareholder Eddie Lampert told the company's board that it was crucial it restructure more than $5 billion it owes "without delay," according to a recent regulatory filing.

Investors are giving up hope on a deal. Sears Holdings (SHLD) stock plunged 28% Wednesday. The stock has lost two-thirds of its already depressed value since Lampert announced the attempt to restructure the company's debt on September 24.


Sears revealed Tuesday night that investor Bruce Berkowitz of Fairholme Capital Management dumped 142,000 shares of Sears in the last few days, for only 59 cents to 65 cents a share. The sale represents just 8% of his remaining stake in the company, but it's not a good sign: He may be cutting some of his losses, because shareholders are typically wiped out in a bankruptcy.

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