I think Sears would have been much healthier, much longer, if Kmart would not have swallowed it. If Eddie had never been involved, then the many billions that were frittered away on stock buybacks would have been used to maintain stores, buy merchandise, etc.
But really, it goes back to Alan Lacy, who was never CEO material. He was afraid to do anything -make any investment. What should have happened was that the mall-based stores be sold, and have the company migrate to new locations closer to the customers, which were focused on soft goods, or appliances, or tools. We stayed mall-based, and full line store based far beyond what made sense. Consequently, we were unable to make the changes needed later on.
Perfectly put by @TSqMvUC-xoi.