For Mr Miller's bosses, however, fortunes look brighter.
Laments like Mr. Miller's have surfaced repeatedly in recent years, amid a wave of bankruptcies in the US retail sector that has claimed household names such as Toys R Us, Payless Shoe Source and Nine West.
Eileen Appelbaum, co-director of the Center for Economic and Policy Research in Washington, says those deals limited Sears' ability to invest in the future – just as the need to compete with online shopping made those investments critical.
ESL has defended its actions, saying "all transactions were done in good faith, on fair terms" in order to keep Sears in business.
It said it was confident that its process for reviewing deals for conflicts of interest was "unimpeachable".
They cite concerns like those of Ms. Appelbaum and Mr Miller's.
"ESL's current bid to 'save' the company is nothing but the final fulfilment of a years-long scheme to deprive Sears and its creditors of assets and its employees of jobs while lining Lampert's and ESL's own pockets," attorneys for a group of unsecured creditors wrote.
But that was an exception, contingent on those firms' largesse.
Who will the 'retail apocalypse' claim in 2018?
Carrie Gleason, who helped organise the worker campaigns as a policy director for Organization United for Respect, says the Toys R Us bankruptcy marked a "breaking point" for broader awareness of the way business strategies contributed to retailer failings.
But with retail's struggles expected to continue, more pressure is needed to bring change, Ms. Gleason says.
"This is not going to be the last [bankruptcy]," she says.