Is because no one believes that anyone could believes that anyone could have intentionally run Sears this badly for the past 14 years, or failed at the bankruptcy this hard for the last two months. Eddie doesn't understand capital, period. He's not just bad at it, he's a complete imbecile. Profit generating assets have to be maintained, or they lose value. Assets depreciate over time until they become worthless, but their lives can be extended. Money goes in, and if invested well, returns come out. To him, as an investor, it was never more than a magical black box where things happened as if by magic. Even after fourteen years, the lightbulb never went on.
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Stitch in time
The problems started the moment he bought the company. He never understood the basic idea that a stick in time saves nine. Fixing something early is very cheap. The longer you wait, the costs compound, until a hundred dollar fix turns into a million dollar one out of pure negligence. Costs compound. Again, Eddie does not understand the basic nature of capital, and that is why he failed.
Lampert kept pouring money into the company trying to keep it afloat - though it's a badly kept secret that he wasn't trying to save the stores. The only way Sears could pay him back was the real estate the stores held. That's one of the reasons this recent bid failed, was because he wanted them to give him the land in exchange for more cash to keep running. Investors finally said enough is enough, and they'd rather liquidate (and get a better deal on the remaining assets, including the real estate) rather than let Eddie try to buy them for pennies on the dollar.