Lampert, through his hedge fund ESL Investments, has agreed to give the company a $500 million loan backed by Sears' properties.
Backing the loan with Sears' real estate means that if the company goes under, Lampert and ESL could be among the first to collect, according to bankruptcy experts.
It's the second time in a week that Lampert has thrown money at the business to keep it alive.
Sears shares have rallied by as much as 20% in the past five days, and they were up about 2% on Wednesday's news.
Last week, Sears announced that it had obtained a loan called a secured standby letter of credit from ESL for an initial $200 million, with the option to expand the amount to $500 million.
Sears says it will use the newest loan to fund operations while it prepares to market and sell some of its real estate. The proceeds of the future sale will be used to pay off its debt, the company said.
Sears shares.(Markets Insider)
Sears has previously raised money by selling off its real estate.
In 2015, Sears launched and spun off a real-estate investment trust called Seritage Properties and sold 235 of its stores in a lease-back arrangement to the new company. Sears made $2.7 billion off the sale.
The retailer continues to pay rent to Seritage for most of the stores, but it has started closing some of them.
Seritage announced Wednesday that Sears would terminate leases on 19 properties. Sears did not respond to requests for comment on whether those 19 properties were in addition to the 48 closings that Business Insider reported last week.
Over the past two years, Lampert and his hedge fund have loaned Sears more than $800 million — not including these most recent cash infusions — to keep the business in operation.
In the most recent quarter, Sears' revenue fell by 13% to $5 billion and losses widened to $748 million from $454 million in the period last year.
Same-store sales dropped 7.4%, including a 10% decrease at Sears stores and a 4.4% decrease at Kmart stores.
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