‘Transparent Terms’
Nothing Lampert won out of Sears’s spinoffs was the result of special treatment, said Paul Holmes, a spokesman for ESL. “As we have said previously, the Land’s End and Seritage transactions were carried out on transparent terms that delivered value to all Sears shareholders and every shareholder had the same opportunity to participate.”

The defeat of a bankruptcy filing won’t dull Lampert’s passion, according to people close to him. He’ll continue to lead his low-key billionaire life, reading, riding his racing bicycles and spending time on his 288-foot yacht. (Lampert named it The Fountainhead, after the 1943 novel by Ayn Rand, whose books glorify individualism and the pursuit of riches.) And looking for deals. It hasn’t been unusual for him to walk out in the middle of dinner parties organized by his wife to hunch over his phone or a computer in another room, according to people who have attended the events, and on occasion, he hasn’t shown up for the meal at all.

Hitting Home Runs
Lampert started ESL -- for Edward Scott Lampert -- in 1988 after three years at Goldman. Richard Rainwater, who oversaw the Bass brothers fortune, staked him $28 million to get going.

By the time he was 43, he was a billionaire three times over. He hit home runs, the most impressive with the auto-parts retailer AutoZone and the car seller AutoNation Inc. His clients saw annualized returns of more than 20 percent after fees until 2001. Even with the Sears fiasco, an investor who has been with Lampert from the beginning would now still be enjoying an annualized return of about 12 percent.

He had what looked like another success on his hands in 2002, when he bought Kmart’s unsecured debt for around $700 million. Within two weeks, he’d orchestrated the retailer’s exit from bankruptcy and emerged as its biggest shareholder.

Kmart was throwing off cash back then, and Lampert masterminded the merger with Sears. It wasn’t immediately a disaster, but losses started piling up.

Four CEOS
Sears rolled through four CEOs in eight years, and Lampert took over in January 2013. But he shows up at the headquarters outside Chicago only a few times a year. He prefers to beam in from his office in Florida; while he still owns a home in Connecticut he lives most of the time in a $40 million estate on Indian Creek, an island in Key Biscayne that’s home to two dozen or so of Miami’s uber wealthy.

As he cut costs to the bone, he pitted executives against one another in a battle for scarce resources in a sort of a retail Hunger Games, people who worked for him said. He ruffled feathers by being a micro manager with little interest in heeding the advice of top executives, according to one former high-ranking employee, who like others interviewed for this story asked not to be named for fear of angering Lampert. Another person recalled an uncomfortable conference call during which Lampert cut off one of his own executives, with an investor also on the line, with a quiet but dismissive, “That’s idiotic.”

Perhaps his biggest misstep was thinking he could power through the recession. He had the opportunity to cancel a massive number of leases on Sears stores in the aftermath of the financial crisis, according to people familiar with the company. Instead, he renewed them.

Rainwater, who died in 2015, had pulled his money out of the fund when Lampert decided to move beyond picking stocks to takeovers and buyouts, thinking the young man wasn’t ready. Part of it, Rainwater told the Wall Street Journal in 1991, was what he saw as the downside to Lampert’s exceptional drive: “He’s so obsessed with moving in the direction he wants to move that people get burned, trampled on, run into.”