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The potential bankruptcy of Sears is really a lesson in timing: It might have had a shot if its chief executive, Eddie Lampert, had ripped off the Band-Aid six years ago.

A deadline for Sears to make a $134 million debt payment hits on Monday, and the company has already missed payments to some vendors, Reuters reported on Thursday. Mr. Lampert, who is also the chairman and top shareholder of Sears, has bailed out the chain in the past. He and his fund, ESL Investments, are owed $2.5 billion as a creditor. His proposal to infuse $480 million into Sears and carry away some assets has been rebuffed by a special committee of directors. Other creditors have reached the end of their rope.

It’s easy to see why. Even among a sea of retail failures — from Toys “R” Us to Mattress Firm, which filed for bankruptcy protection last week — Sears’ failure is dramatic. Mr. Lampert acquired the company in an $11 billion deal in 2005, and merged it with Kmart, which he already owned. The market capitalization of Sears has fallen from nearly $30 billion to around $40 million in a decade.