@wwj - You stole the words out of my mouth. There has been so much speculation as to when Sears will die. I have been hearing this speculation for quite a while, actually, I've heard it since I started with the company in 2013.
There is no doubt that Sears Holdings will not go through bankruptcy, we just don't know when. Just as we think "this is it", Lampert comes to the rescue with a cash infusion (loan). I don't think that he will continue doing this for much longer, and most likely, that's when we will enter our final stages of our demise.
He's been doing this since 2014, $500 million here, $100 million there. It all adds up and it is just not sustainable. His potential ROI seems pretty dismal. Retail property is in overabundant supply. Look at what happened in the 2008 real estate crash, thousands of homes suddenly on the market, so home prices went south. Same kind of thing is going to happen with retail real estate. Even Target and Walmart are closing stores; our typical store is an older building located in an area with average or less-than-average potential while their properties are usually newer with more potential, so Lampert is at a disadvantage on that front. Some are "ring-fenced" for pension, others are free for the taking as his collateral in a bankruptcy event, but can he sell them and realize a gain on these transactions?
There isn't a whole lot left in the IP (intellectual property) portfolio. Kenmore and DieHard are all that are left, maybe SYW too and a few "small potatoes" (e.g. Simply Styled). There wasn't exactly a line of companies wanting to buy Craftsman, of which I believe the proceeds of that sale went towards the pension and short term obligations, so who will buy Kenmore and DieHard (and SYW, etc), and in the event of a bankruptcy, assets usually don't go for top dollar.
I'm not even a hedge fund guy and I can see that he has an albatross on his hands. I wonder if or when he realizes this, and if he does realize the huge flop this has been, is he taking strategic steps to salvage as much of his ROI as possible? Is he "underwater"?
The world today is a lot different than it was in 2004. This real estate play has been a losing battle. I'm surprised he didnt just walk away from this a few years ago.