By the time Sears Holdings filed for bankruptcy in 2018, it had surely reached some sort of financial engineering singularity, if such a thing is possible. Under Eddie Lampert's majority ownership and executive stewardship as CEO, a headache-inducing web of interrelated financial relationships had been created around and through the retailer. When all the asset sales, spinoffs and loans were finalized over the course of more than a decade, Lampert and his hedge fund were Sears' largest shareholder and lender, as well as a major landlord and supplier. Read more at Retail Dive.