Via Crain's, Business Insider explains in detail how Eddie Lampert has structured his financial holdings so that he may benefit more from Sears' destruction than from its success:
For all the problems in Sears stores, Lampert has set up his various businesses in a way that means he has other ways to gain no matter what happens to the company.
ESL holds a majority share of Sears, and that stake has lost three-quarters of its value just in the past few years — more than $1.5 billion since early 2015 alone.
But Lampert, through ESL, has loaned Sears more than $1.12 billion and promised an additional $679 million over the past two years to help keep the company afloat. In return, Sears pays origination fees and interest directly to ESL, and, by extension, Lampert. A recent shareholder complaint claims that Lampert and ESL made at least $19 million in fees and interest payments from a $400 million loan in 2014.
Lampert and ESL could potentially seize stores and inventory if Sears can't pay its bills. That $400 million loan, for instance, is backed by collateral of 25 stores valued at $500 million total.
Even if the company went bankrupt, Lampert wouldn't walk away empty-handed, according to bankruptcy experts and former executives.
How on earth did Sears' board allow this to happen? Oh, right—Lampert owns 54% of the company, and so appoints the board.
There are shareholder lawsuits, of course, though it's doubtful they'll succeed. And so the murder continues.