It might not happen, but most of the financial guys are saying something will. Not sure that Sears will disappear completely, but changes are definitely coming. Some have suggested that they go back to being a mail-order company like they were originally, just be internet based. Not sure how that would work out, but their stores are pretty sorry. No updates in decades, usually empty, piss poor displays, etc.
At the least, I would suspect that their profitable brands would be parted out and sold off. Kenmore and Craftsman could both live on without Sears, and I'm sure someone would be interested in buying them if it came to that.
Craftsman stuff is pretty hit and miss now, a lot of their tools are made overseas. Supposedly most of the higher end hand tools are still made here, I pretty much only buy the "professional" grade stuff. Their standard tools don't seem that high quality, and their "Evolve" brand is made in China.