If you walked into a Sears in 2026, you’d probably feel like you stepped into a "liminal space" meme. The lights are dim. The shelves are half-empty. It’s a ghost of a retail empire that once defined the American middle class. At the center of this slow-motion collapse is one man: Eddie Lampert.
For years, people called him the next Warren Buffett. He was the wunderkind who went from a Goldman Sachs arbitrage desk to running his own hedge fund, ESL Investments, by age 26. He even survived a terrifying 28-hour kidnapping in 2003, reportedly talking his way out of it by promising his captors millions.
But his legacy isn't tied to his survival or his Yale degree. It's tied to the messy, controversial, and ultimately devastating decline of Sears Holdings.
The $11 Billion Gamble That Changed Everything
In 2004, the retail world was stunned. Kmart, which had just crawled out of bankruptcy, was buying Sears, Roebuck & Co. for $11 billion. It was Lampert’s brainchild. He believed that by merging these two struggling giants, he could create a powerhouse capable of taking on Walmart and Target.
At first, the market loved it. Sears Holdings stock soared, hitting over $190 a share in 2007. Lampert was the richest man in Connecticut. He didn't focus on "retail" in the traditional sense, though. He didn't care about floor displays or fashion trends. He cared about the data. He cared about the real estate.
While competitors were pouring money into store renovations and e-commerce, Lampert was doing something different. He was cutting costs. He was buying back stock to keep the price high. Most famously, he restructured the company into 30 separate business units.
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He wanted them to compete with each other. He thought "internal free markets" would spark innovation. Instead, it sparked a civil war.
Department heads started fighting over floor space. The "tools" guys wouldn't talk to the "appliances" guys. Marketing budgets were slashed. By the time Amazon really started eating everyone's lunch, Sears was too busy fighting itself to fight back.
Was Sears Holdings a Retail Play or a Real Estate Strip?
This is the big question that still haunts the business world. Did Eddie Lampert actually try to save Sears, or did he just want the land under the stores?
Critics, including former executives and disgruntled creditors, have long alleged that Lampert was "stripping" the company of its most valuable assets. Look at the timeline:
- 2014: Sears spins off Lands’ End.
- 2015: Sears sells 235 of its best properties to Seritage Growth Properties, a real estate investment trust (REIT) where Lampert was the chairman and a major stakeholder.
- 2017: The iconic Craftsman brand is sold to Stanley Black & Decker for $900 million.
The irony? As Sears got more desperate for cash, it ended up borrowing money from Lampert himself. By 2018, ESL Investments was the company’s largest creditor and its largest shareholder. He was the landlord, the lender, and the boss.
When Sears Holdings filed for Chapter 11 bankruptcy on October 15, 2018, it felt like the inevitable end of a long, painful slide. But Lampert wasn't done. In a move that felt like a movie plot, he won a bankruptcy auction in 2019 with a $5.2 billion bid to buy the remaining assets through a new company called Transformco.
Where Things Stand in 2026
Honestly, the "new Sears" is barely a retail company anymore. As of early 2026, the number of full-line Sears stores on the U.S. mainland has dwindled to a handful—roughly five to eight locations, depending on which closing sales are currently active. Places like Burbank, California and El Paso, Texas still host these retail relics, but they feel more like museums of the year 2005 than modern stores.
Transformco has pivoted almost entirely to real estate development. They aren't trying to sell you a Kenmore dishwasher as much as they are trying to turn old mall parking lots into "multifamily residential units" (apartments).
The Financial Reality
Despite the destruction of value for common shareholders, Lampert has remained a billionaire. While his net worth took a hit—dropping from over $3 billion at his peak to around $2 billion in the mid-2020s—his stakes in AutoZone and AutoNation have kept him afloat.
He still lives in a $40 million mansion in Miami’s Indian Creek Village, often referred to as the "Billionaire Bunker." He still owns the Fountainhead, a 288-foot superyacht.
What Most People Get Wrong About the Sears Collapse
It’s easy to say "Amazon killed Sears." That's the lazy answer.
The truth is more nuanced. Sears survived the Great Depression. It survived World War II. It was the original "everything store" long before Jeff Bezos was born. It died because of a failure to invest.
Retail is a high-capital business. You have to fix the roofs. You have to update the checkout systems. You have to make people want to be there. Lampert’s philosophy was that capital should be allocated to the highest return, and in his mind, that was never a new coat of paint for a store in a dying mall.
He bet on a loyalty program called Shop Your Way, thinking data and digital coupons could replace the physical experience. He was wrong.
Practical Takeaways from the Lampert Era
If you’re a business owner or an investor, there are some pretty harsh lessons to be learned from the Sears saga:
- Financial engineering isn't a strategy. You can’t "math" your way out of a bad customer experience. If the stores are dirty and the staff is unhappy, the stock price will eventually reflect that.
- Silos are deadly. Pitting your own departments against each other for resources might sound "Ayn Randian" and cool in a boardroom, but in practice, it just breaks the company.
- Watch the "Double-Ended" deals. When a CEO is also the lender and the landlord, the conflict of interest is unavoidable. Investors should always look at these "related-party transactions" with a skeptical eye.
The story of Sears Holdings and Eddie Lampert is a cautionary tale for the ages. It’s a reminder that even the biggest icons can fall if they lose sight of the people who actually keep them alive: the customers.
For those interested in the remaining footprint, you can still find Sears Home Services operating in many areas. They still repair appliances, even if the store where you bought the appliance is now a pile of rubble or a luxury apartment complex.
To see the current list of remaining Sears and Kmart locations, or to track the ongoing redevelopment of their real estate, you can monitor Transformco’s property portfolio or local commercial real estate filings in your city. It's the best way to see which mall anchor is about to become a condo next.