The company is in talks for financing that would fund operations through bankruptcy, said the person, who asked not to be identified because the discussions are private.
Lampert - Sears' largest shareholder and creditor and the owner of the hedge-fund ESL Investments - asked creditors last month to refinance $1.1 billion in debt before the October 15 payment, according to a filing with the U.S. Securities and Exchange Commission.
Lampert's efforts to keep Sears out of bankruptcy have included shedding hundreds of unprofitable stores: Sears and Kmart had some 3,500 locations when they merged under Lampert in 2005; now there are about 900 nationwide. The Journal also reported the billionaire Lampert, who has rescued the company in the past, could make the payment to avert an in-court restructuring. Lampert and ESL are the company's two largest shareholders. The company is now $5.6 billion in debt.
The company separately said it named restructuring expert Alan Carr to its board of directors. While the SPDR S&P Retail ETF (XRT) is up 6.5% year to date, and fellow department stores like Macy's (M), Kohl's (KSS), and Nordstrom (JWN) have climbed more than 30% since the start of the year, Sears has lagged-and how.
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.
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But the retail landscape is littered with out-of-business brands that tried to reorganize in the bankruptcy process and liquidated their businesses instead.
Sears, which was the world's largest retailer in the 1960s, has been struggling in recent decades, in the face of declining foot traffic at its brick-and-mortar stores as online shopping gains popularity. Share prices of JCPenney, Kohl's and Bed Bath & Beyond were up as of midday Wednesday, which Kopsky said was an indication that the market believes Sears will file for bankruptcy and that those retailers will benefit in the near term.
Sears was at one point America's largest retailer and its largest employer.
In July, Sears closed its last store in Chicago, once its hometown.
The 125-year-old company, which has not turned a profit since 2010, has approached several banks to prepare for a bankruptcy filing, according to CNBC. Toys "R" Us' creditors lost faith in the retailer after revenue during last year's holiday season failed to meet their expectations.