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I'm under the impression him and his group became controlling shareholders of Sears and asset stripped it. That is technically legal but Sears sued him for infringing on the other shareholder's rights during the process. https://en.wikipedia.org/wiki/Asset_stripping Lampert is also part of the group offering the lifeline loan. So he helped drain the company and is now going to profit from the loan to keep them alive.

Or he’ll lose his money on the loan too. That $500 million will all go down the drain if the company doesn’t have a turnaround. A loan is giving someone else money and you only profit if they pay you back in full with interest after all.

I saw a different article criticizing him for basically throwing his money away trying to keep Sears going... http://money.com/money/5498143/eddie-lampert-trying-to-save-...

> While Lampert hasn’t suffered like his employees, Sears’ decline has cost him: Since taking over as CEO in 2013, he’s lost almost half his fortune – once as large as $3.1 billion. During his peak before the financial crisis, Lampert managed over $15 billion at his hedge-fund. As his bet on Sears soured over the years, more and more investors abandoned him. By the end of 2017, ESL managed only $1.3 billion, according to filings with the Securities and Exchange Commission.

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