He is totally out of touch with reality. He has made his managers too afraid to tell him the truth; he doesn't want to hear it.
He's also raided his own company's real estate assets, transferring them over to another corporate holding entity he controls, at discount prices below going market rates. If the allegations of lawsuits brought on by Sears shareholders are true, he has basically been stealing billions from the company to line his own pockets. Maybe he doesn't actually care so much about the wellbeing of the Sears company, just wants to ravage it for all it's worth.
A real Wall Street shark.
He can conveniently blame the death of his company on online competition from Amazon, but in this economic climate, Sears should not be struggling. Per capita retail spending is actually slightly up from what it was before the Recession, and rising rents cannot explain the problem either since Sears actually owns (or used to own) a large amount of its stores.
Sears stores are going out of business right and left, all their brand name appliance names are being sold off, and no one is buying from their online site.
Of course, the way he's set up everything, even if his company goes under, he still wins.
This just sounds like another case of private equity using leveraged buyouts to parasitically raid publicly-traded companies, leaving big companies a hollowed out shell of their former selves and screwing the other shareholders.
By the way, who are these shareholders that are getting screwed?
It's mostly older retired people with pension funds. Public teachers, for example. The state has set up a pension fund system for them, with investments in corporate stock like Sears, even if these teachers do not know it.
You could (indirectly) own Sears stock without even knowing it, if you have a mutual fund in your retirement savings investments, or if you are a public employee and they have set up a retirement pension system for you.
If enough of these stocks go under, then they'll have to modify the terms of the pension system and reduce your retirement payments.