Kmart chairman Edward Lampert listens during a news conference to announce the merger of Kmart and Sears in New York . Kmart is acquiring Sears, one of the most venerable names in U.S. retailing, in a surprise $11 billion deal that will create the nation's third-largest retailerKMART SEARS MERGER, NEW YORK, USA

Shares of Sears Holdings Corp. fell 26.5 percent Wednesday in pre-market trading on rumblings that the retailer could be far closer to a bankruptcy filing than initially thought.

At 9:23 a.m., shares of Sears were trading at 43 cents on the NasdaqGS exchange.

Company chairman and chief executive officer Edward S. Lampert has been trying to effect a bailout over the last few weeks that would eliminate $4.35 billion of Sears’ debt load. It has $134 million in debt due on Monday. The company on Tuesday said it added restructuring expert Alan J. Carr to its board.

Lampert’s plan includes his hedge fund ESL Investments buying $1.47 billion in Sears assets that includes its Kenmore brand and the Sears home improvement and services businesses. The Sears chairman holds a 50 percent stake in the company. That stake includes a 31 percent stake in personal holdings and a 19 percent stake held by ESL. Lampert is also the chairman of ESL.

Fitch Ratings, a credit ratings agency, said last month that even if Lampert were able to help Sears with a bailout, it might not be enough to avoid a bankruptcy filing. The ratings agency said Sears has annual liquidity needs in “excess of $600 million.”

And Lampert himself last month, when Sears posted second-quarter results, raised the possibility of a bankruptcy filing. According to a Wall Street Journal report late Tuesday, Sears is working with M-III Partners to prepare the filing. And CNBC said the company has been in talks with banks regarding financing while in bankruptcy court.

When Lampert took Kmart and merged it with Sears, Roebuck & Co. in 2005 to create an $11 billion deal to form Sears Holdings, the combined entity was projected to have annual revenues of $55 billion and more than 3.500 stores in operation. Sears now has 866 stores in operation. A further consolidation of its retail space would likely have implications for many of its retail competitors, such as J.C. Penney and Kohl’s.

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