I discussed this with folks who have been around since the 70’s with SEARS.
This guy came in with one goal. Reap the rewards of the giant. He won.
The biggest surprise was that he ran it as long as he did. He bought KMart out of bankruptcy for the real estate value, and quickly monetized that, then bought Sears. Some folks thought he’d run through that like he did the good KMart assets. But he put 10 years into trying to keep the chain running. So this wasn’t your typical investment banker looting.
Looks like he may be willing to take one more round with a few hundred stores. I can’t see where the pleasure is worth the pain at this point. Maybe nostalgia on his part.