Among other assets, Sears has a real estate portfolio that could be conservatively to fairly valued at over $2 billion, he said. The analyst was basing the estimate on the amount competing department store operator J.C. Penney (JCP) was able to borrow against its real estate, keeping in mind that Sears has more stores as well as locations that are as good as or better than J.C. Penney, he said.

There is also Sears Auto Center, the warranty business, and the 51% stake in Sears Canada (SCC) that has a market cap of C$1.7 billion ($1.5 billion), as well as the Craftsman, Diehard and Kenmore brands.

However, if the plan is to enact a turnaround, it's also "pretty clear [Lampert] has a lot of work to do to transform Sears," Tuhy added.

Lampert said in his annual chairman's letter that the company would focus on integrating e-commerce and mobile with brick-and-mortar, increasing the use of technology in Sears department stores and building the company's brands. However, the plan doesn't include putting money into renovating the chain's dilapidated stores, as The Deal previously reported, something that customers are unlikely to find inviting.

And there are plenty of other places for those customers to go including Home Depot (HD), Macy's (M) and the ever-present online giant (AMZN).

Sears Holdings could even resort to spinning off Kmart, one source said. It would likely not be until after a number of these moves that Sears would resort to a more radical financial restructuring or a bankruptcy filing, the person said.

In regard to Kmart, however, Tuhy said, "We consider the viability of Kmart (which represented around 41% of domestic sales in its latest fiscal year), as uncertain given its continued challenges as evidenced by its meaningful operating losses and market share erosion."

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