People often blame Eddie for the fall of Sears, but Sears fell for reasons that have nothing to do with him. Look at JCPenney, Neiman Marcus, Forever 21, Sports Authority, Radio Shack, Payless Shoe Source, and J Crew. All major chains that went bankrupt for reasons that have absolutely nothing to do with Eddie Lampert. Eddie recognized from the very beginning that mall department stores as a universal destination were on the clock, and set about to transforming to company into one that would survive, and that the future was eCommerce. Target didn't start out as Target, it used to be Dayton Hudson. You can try out many formats, and many of them can fail. You only have to find the few that succeed, and that will bring you to the promised land. Eddie called Sears a $50 billion dollar startup, and it was true. Sears' purpose was to find the next big thing.
In the early days, he tried turning a number of Kmarts into Sears Essentials. People say he never invested in the stores, but that's not true. He invested heavily into remodels, did the test marketing, and spent a lot of cash and advertising. And the return on investment wasn't there. He learned then that pushing a lot of unnecessary investment into stores was not the future.
Instead, pushed forward with ideas like curbside pickup, Shop Your Way, and internally, Pebble. People may have scoffed at these, but the integrated retail shopping and social media experience has wildly succeeded in China. It has proven itself. Even the limited Amazon review system and GoodReads can be considered a primitive social networking system of sorts. He green lighted cloud projects at Sears and other significant technology initiatives. Perhaps they didn't pan out, but the idea was always to let Sears serve as an incubator, and separate out the company into independent units instead of letting groupthink suppress ideas, where the winners would get the most funding and snowball into success.
Unfortunately, Sears is not a startup, and did not get preferential treatment from the stock market or the media as enjoyed by Amazon, eBay, Netflix or Tesla. These companies are allowed to operate in billions of losses for years with favorable coverage and are allowed to raise unlimited capital which Sears was not unable to enjoy. Amazon happily ran Prime at a loss for years, before eventually having to double their membership price, and no analyst ever insisted on it no matter how much the company stonewalled them. Despite having many billions in assets which were successfully sold off, the press relentless attacked Sears and soured its relations with vendors causing friction and worry. Worst of all, Sears inherited the excesses of generations past, in the form of pensions and retiree insurance, billions in obligations that no newer company had dragging on their future like an anchor.
Eddie has been proven right. The future was malls as evidenced by retail failures. The future was always in eCommerce, and the social media + online sales model has been proven. Strong businesses like Lands' End and Seritage have been spun off as their own concerns, and Sears shareholders were rewarded with their own ownership. Sears and Kmart are still looking to leverage their core strengths to emerge and transform into a stronger entity than ever. All it takes is are great ideas and execution to build on that powerful core.