Sears Holdings Corp. (SHLD) shares collapsed to a fresh record low Wednesday amid reports the struggling retailer could seek bankruptcy protection in the coming days as it scrambles to appease creditors ahead of a looming debt payment deadline next week.

The Wall Street Journal reported that Sears has hired bankruptcy advisors M-III Partners LLC to help it prepare for a possible Chapter 11 filing, just one day after it added restructuring expert Alan Carr to its executive board ahead of an Oct. 15 payment deadline for $88.5 million in outstanding Sears bonds -- alongside $44.5 million in company loans -- that could test the group's balance sheet as it struggles to survive long enough to tap into the consumer spending boom expected in this year's holiday shopping season. 

Carr, who also heads Drivetrain LLC, a restructuring consultancy, will remain on the Board until Sears' 2019 shareholders meeting, the company said Tuesday in an SEC filing, with CEO Eddie Lampert extolling his "deep experience as a director for companies that went through complex organizational change." 

Sears shares were marked 36.5% lower in the opening minutes of trading in New York Wednesday and changing hands at a record low 37 cents each, move that values the Hoffman Estates, Ill.-based retailer at just $44 million.

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Last month, Lampert's ESL Investments Inc. filed a restructuring plan with the SEC that included the sale of its encumbered real estate portfolio and debt swaps with second-lien and unsecured creditors, a move it said would reduce the department store chain's current $5.6 billion in debt to about $1.2 billion, cut annual interest expense by $33 million to $88 million and extend debt maturities.

However, Lampert, who serves as both group chairman and CEO, is also its controlling shareholder and perhaps Sears' most important creditors. In fact, an analysis of Sears' debt by TheStreet's sister publication, The Deal, found that at least $1.6 billion of Sears Holdings loans are held by affiliates of Lampert's ESL Investments.

"Conceivably, Sears could enter bankruptcy, shed some of its debt, strike deals with other lenders and Lampert could wind up with ownership of whatever's left, including a significant amount of potentially valuable real estate," TheDeal's Stephanie Gleason argued.

That might not be much consolation for a company that has shed more than $11 billion over the past six years, shuttered hundreds of stores, fired thousands of employees and watched its stock fall from a record $133 a share in the days leading up to the global financial crisis to its penny stock valuation of today.

"We will now be working aggressively to execute liability management transactions so that we can extend our runway and continue executing on our transformation strategy," Sears told employees last month. "At the same time, we'll continue to move forward with our other planned liquidity and cost measures."