Evaporating Share Value
Lampert has maneuvered out of tight spots before, most famously when he persuaded four men who kidnapped him in January 2003 to let him go after holding him for 30 hours, blindfolded and handcuffed, in a motel bathroom. But saving sinking Sears required more than fast-talk.

His last idea was a debt restructuring that received little or no support from other creditors, who saw it as a scheme to allow ESL to be paid for Sears’s real estate, according to a person with direct knowledge of the situation. Part of this Lampert plan was to have unsecured creditors swap their debt for equity, a fool’s trade in the view of most analysts.

Related: How Sears Got Left Behind as Walmart, Amazon Took Over Retail

There’s no question Sears has cost him, and not only in reputation: He saw about $240 million worth of stock that he personally purchased evaporate as the shares tumbled. Another $287 million that he received in compensation has all but disappeared. ESL has lost $65 million just this year.

Earning Fees
The hedge fund’s assets plummeted to around $1 billion from $15 billion in 2006 as the portfolio shrank from a half-dozen to the one massive crapshoot on Sears. The big-name investors exited, and so did Goldman Sachs Group Inc. clients who had come into ESL as part of a $3.5 billion capital raise in late 2007 and early 2008.

Still, as Sears’s major debt holder, with roughly half of the company’s $5.3 billion total, ESL saw a bit of upside, extracting more than $200 million in interest payments a year.

And Lampert carved out what looked like -- and in some cases might yet be -- saves for himself, with spinoffs that gave him chunks of equity in new companies. One was Seritage Growth Properties, the real estate investment trust that counts Sears as its biggest tenant and of which Lampert is the largest shareholder; he created it in 2015 to hold stores that were leased back to Sears -- cordoning those off from any bankruptcy proceeding. He and ESL got a majority stake in Land’s End Inc., the apparel and accessories maker he split from Sears in 2014.

‘Colossal Failure’
The Sears Canada Inc. gamble was a fumble; that spinoff began liquidating one year ago. Lampert and ESL together had almost $300 million in that stock and both rode it to zero, though they did pocket $25 million in special dividends. Lampert is the chief shareholder in the Sears Hometown and Outlet Stores Inc., a stock that has tanked along with its former parent.

All those spinoffs robbed Sears of assets when it needed them, said Mark Cohen, a former CEO of Sears Canada and frequent Lampert critic who’s an adjunct professor of retail studies at Columbia University. “This completely unconventional way of managing a business might have been an interesting alternative operating strategy were it not for the fact that it has been a colossal failure.”

Over the years of propping Sears up, Lampert threw his own money into the effort, and his friends and supporters said this wasn’t only in self interest: He wanted to keep the lights on and people employed. He and ESL were willing to lend at much lower rates than others were demanding. He had Sears pay almost $2 billion into the unfunded pension plan in the past five years.