Sure the market change fast, but remember that the likes of Target was years away from an Internet retail presence when Eddie took over, while he managed to lose a metric bu-t-ton ok the Seritage properties and even the near unassailable competitive is Sears appliance, mattresses and tools, because he thought he could economize Sears like AutoZone.
From 425 go forward to Shaq's shoe size is pretty darn impressive, and between cons like Innovel, DieHard, Citi, Craftsman, he's almost managed to pay off the interest from the borrowing fiascos that came from Sears and the the huge money borrowed for Seritage. It's kind of funny how he always bragged about not selling Sears stock then dumping them in the pink sheets at the final minute. If he'd sold near the top he might still be held as today's great financial engineers instead of one of a historically inept CEO.
He bought into his own hype that he was a misunderstood once in a generation transformational genius without understanding that statisticians had modern efficiency practices and metrics had long left his primitive 20th century math in the dust. Should have stuck to wheeling and dealing. Speed of turnover is everything for ROI, and it's weird that he couldn't apply that to real estate, retail, or even financial engineering which was his alleged area of expertise. Well, he surely was misunderstood, because no one could figure out why he seemed to be deliberately and aggressively losing money like his life depended in it.