Why does Eddie remind me of Clark Griswold in the National Lampoon's Vegas Vacation? He keeps betting away, getting nowhere in the process. It would have done him good to BK maybe five years ago. Only instead of a casino, this is about selling SHLD piecemeal. How is he going to get rich off of 300-some-odd stores (in a market that will soon be supplying more commercial real estate than the demand, seeing how retail is imploding). Same thing with Seritage...rents for commercial retail will not be so high with retailers closing stores.
How will he realize a ROI on SHLD's IP when the bills are coming due for things like the pension? The Craftsman sale will be mostly going towards pension obligations. Who knows how much Kenmore/DieHard will bring in, or for that matter, the auto centers and the service company. If anything else gets sold before BK, SHLD will burn it up in no time in operating costs. If it sticks around up to BK, naturally, it will go for pennies on the dollar (heck, the IP will not get SHLDs asking price even before bankruptcy...most stronger companies work this to their advantage by paying a pittance for an asset that a weak company would rather have sold, just to have some cash flow).
Eddie may be in line as a creditor come BK and he will get his stores but how much will they be worth? I'm betting not much. There's a whole lot of negative to go with the soon-to-be flooded commercial retail RE market, like old asbestos-ridden stores attached to declining/dying/dead malls (take your pick) or in an area where merchant activity largely packed up and left a decade ago. If those stores sit too long the tax bills and upkeep will catch up. Cities may start fining for empty and/or derelict buildings.
Something to think about. I don't think Eddie will be getting quite the payday everyone is thinking of.
I really, truly believe Eddie is in way over his head and it will turn out that he will have lost a LOT of money. I'm betting that by the end, he will have invested more than what he gets back, even after the ring-fenced assets are transferred to him during BK.