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I think Lampert sort-of-kind-of knew what he was doing.  I agree he had an ulterior motive and was playing hedge fund high finance games to position himself to receive the greatest financial benefit if Sears turned around, while minimizing his exposure.

I think however two things happened over the years that got in his way.  First, I think Lampert got into his head the idea that he wanted to be known as the guy who turned around an American icon like Sears as well as KMart. It wasn't enough to be rich, or known as an investment whiz kid, he wanted to be known as a brilliant businessman.   Jack Welsh, Bill Gates, Warren Buffet, and ... Eddie Lampert!  One little known fact is that Lampert was the largest shareholder at AutoNation, at one point owning more than half the company.  Guess who started buying a lot of AutoNation stock, while Lampert sold, and a couple years ago became AutoNation's new largest shareholder?  Bill Gates.  Lampert wanted to be an investment whiz like Buffet, and a business whiz like Gates.  So perhaps he didn't just tear up the company and sell for parts like your average hedge fund type.  Instead he wanted to satisfy his ego and really turn it around.

Second, I don't think the Board and pesky things like SEC let him do all the things he wanted to do. Even the stock market didn't let him do what he wanted.  A few years ago Lampert gave a memorable public rant when Sears released quarterly earnings, complaining that companies like Tesla and Uber can burn through millions of dollars loss every week, and yet are cheered by the market.  Yet Sears sales don't *increase* enough, and the stock drops off a cliff.

And of course, it's obvious that Lampert is actually no brilliant businessman.  So buh bye Sears.

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Department store chain Sears won a reprieve from liquidating Friday after its chairman, Eddie Lampert, submitted a bid in an effort to buy the retailer and keep it alive, people familiar with the situation tell CNBC.

Lampert's hedge fund ESL Investments put forward his tentative proposal for Sears earlier this month with his formal submission due today.

A bid could help divert liquidation, but may not necessarily. Sears' advisors have until Jan. 4 to decide whether ESL is a "qualified bidder." Only then, could ESL take part in an auction against liquidation bids on Jan. 14. They will weigh the value of Lampert's bid against offers to liquidate the company.

https://www.cnbc.com/2018/12/28/sears-chairman-eddie-lampert-submits-bit-for-company.html

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They were Amazon with their mail order catalogs before the internet existed.

All they had to do was embrace changing times.

Goodbye.

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Looks like Lampert is executing his end game now.  Let the clock run out to show the creditors and the Board that his $4.6 billion bid is in the only bid in town.  And he's got some new backers on board. From https://www.reuters.com/article/sears-bankruptcy/sears-chair-lampert-makes-46-bln-bid-to-keep-retailer-alive-sources-idUSL1N1YX16V

"The offer came after Sears’ existing lenders Bank of America Corp and Citigroup Inc, as well Royal Bank of Canada, which was not previously a lender, agreed to provide a $950 million asset-based loan and a $350 million revolving credit line to back Lampert’s bid, the sources said."

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Pouring good money after bad. The brand is worthless.

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Isn’t it the land he’s after? Bankrupt away debt, keep hard assets like standalone stores that represent buildable land in good areas.

Quoted:
Department store chain Sears won a reprieve from liquidating Friday after its chairman, Eddie Lampert, submitted a bid in an effort to buy the retailer and keep it alive, people familiar with the situation tell CNBC.

Lampert's hedge fund ESL Investments put forward his tentative proposal for Sears earlier this month with his formal submission due today.

A bid could help divert liquidation, but may not necessarily. Sears' advisors have until Jan. 4 to decide whether ESL is a "qualified bidder." Only then, could ESL take part in an auction against liquidation bids on Jan. 14. They will weigh the value of Lampert's bid against offers to liquidate the company.

https://www.cnbc.com/2018/12/28/sears-chairman-eddie-lampert-submits-bit-for-company.html

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Where will I go for my action-wear slacks?

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So if they go bankrupt, who will replace my Craftsman tools when they break?

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So if they go bankrupt, who will replace my Craftsman tools when they break?

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Is it against the CoC to post pictures of inside Sears corporate or the stores?  I see all these post, yet wonder how many have some pictures.