Firstly, Sears could easily be lumped in with JCPenney, Red Lobster—even Howard Johnson’s—all of which appealed to the very middle-est of the middle class. As that previously broad group of factory workers, tradesmen, and middle managers has largely been hollowed out and divided into lower and upper middle classes, it was almost unavoidable that Sears would have a great deal to lose.
That said, I think Sears could have handled its inevitable fall from the top a little more adeptly, although I disagree with the notion that Sears was poised for success and just dropped its mail order and online divisions a little too early.
Even if the company had made a more concerted effort to break into e-commerce, I don’t think Sears could have been Amazon because it was an organization too steeped in century-old blue chip thinking. I doubt the suits who brought you the carefully written Wish Book ever would have allowed customers to write their own reviews—“What if they say something bad about the product? Why, I never!” Such a large and bureaucratic entity couldn’t foster the kind of disruptive thinking that builds empires in the Internet era.