Sears Holdings Corp. is back at the cash machine that apparently is Edward S. Lampert.

The department store amended, for the second time in a little more than two weeks, a loan agreement with JPP LLC and JPP II LLC, entities controlled by Lampert’s hedge fund ESL Investments Inc., to tap another $40 million in financing. Lampert, Sears’ chairman and chief executive officer, just loaned the company $100 million in the same fashion, presumably in time for the holiday season.

The new amendment also allows for an additional $60 million to be drawn by mid-November, if additional collateral is put up, which would bring the amended loan amount to $200 million. Sears’ current debt to Lampert through the JPP entities is $524.1 million, according to a disclosure filed with the Securities and Exchange Commission.

While the initial incremental loan was due to be repaid in April, the date has been pushed back to May, but it’s still backed by 66 real property assets. The remainder of the outstanding loan is not due until 2020.

A Sears spokesman said the loan will be used to fund Sears’ operations.

“We continue to focus on actions to provide the company with additional financial flexibility to generate liquidity and demonstrate our ability to manage our business while meeting all of our financial obligations,” the spokesman added.

As for whether the $60 million also available under the second amendment is likely to be drawn, the spokesman declined to speculate.  

When the first $100 million was tapped early this month, a spokesman rejected the idea that the loan signaled any issues Sears was having getting back to profitability, an eventuality the retailer has promised.

Nevertheless, Sears remains on shaky ground. It’s been on the watchlists of debt monitors like Fitch Ratings, which said in August that a Sears is likely to default on its outstanding bonds sometime next year, and Moody’s, which has a Sears rating implying “significant probability of default” within two years.

In what could be another sign of Sears’ future, one of its biggest supporters, Bruce Berkowitz earlier this week left the company’s board of directors.

Berkowitz founded and manages Fairholme Capital Management LLC, the retailer’s second-largest shareholder, which made its first investment in Sears about a decade ago.  

Fairholme still maintains about 26 percent of the company, but just prior to Berkowitz’s exit, Fairholme liquidated one of its funds that held about 1 percent of its Sears holdings.

Fairholme also holds a sizable stake in bankrupt Sears Canada and over the summer, Berkowitz and Lampert said they were considering a joint investment in the retailer, which broke off from Sears Holdings in 2012. The deal fell through and Sears Canada last week was forced to liquidate.

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