Photo: Scott Olson/Getty Images

Sears Holdings (Nasdaq: SHLD) is preparing for a possible bankruptcy filing that could come as soon as this week, ahead of a $134 million debt payment due Monday, according to WSJ. The company also yesterday added restructuring expert Alan Carr to its board of directors.

Why it matters: Sears was to the last century of American retail what Amazon has become to this century — Trailblazing, ubiquitous and iconic.

  • Wild card: Eddie Lampert, the company's CEO, largest shareholder and largest creditor, who believes a bankruptcy filing could be Sears' reputational death knell. He's proposed a severe slim-down plan that would include divestitures of real estate and the Kenmore brand, the latter of which he offered to buy for $400 million.

The bottom line:

"This is the inevitable end game of an effective liquidation process that has been going on for many years. Throughout that time the sale of various assets along with injections of cash from Eddie Lampert have kept the ailing retailer from going under. However, the activity is akin to bailing out water from a holed ship: It keeps the vessel afloat for longer but does nothing to sort out the underlying problem."
Neil Saunders, GlobalData Retail

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