January 2, 2026
wolterke/Depositphotos.com
As Sears Faces Demise, What Can Be Learned From its Legacy?
As 2025 drew to a close, only five Sears locations remained in operation stateside — in Braintree, Massachusetts; Concord, California; El Paso, Texas; Orlando, Florida; and Coral Gables, Florida. That’s a paltry number compared to the countless locations the retailer once boasted across North America, having become a retail institution since having been founded in the late 1800s.
“If this is really the final chapter of one of the country’s most storied retailers, then it will represent the chronicle of a retail death foretold, reflecting not only changing consumer behavior but also mismanagement and poor strategy,” wrote Forbes contributor Mark Faithfull in a recent analysis.
A large constituent piece of Sears’ downfall is laid at the feet of hedge fund manager Edward Lampert, who managed a controversial takeover of Sears over two decades ago, in 2003. Following that, a merger with Kmart was enacted, in the hopes of reviving the fortunes of two businesses in decline.
“But in truth the bet was less on a phoenix-like retail revival and more on the latent value of the company’s enormous property portfolio. Sears owned much of the real estate for its vast network of stores, an asset Lampert believed could be unlocked even as the retail business withered,” Faithfull wrote.
Sears, Once the ‘Amazon of the Gilded Age’ and Then a Retail Titan For Much of the 21st Century, on its Last Legs
From its position as the “Amazon of the Gilded Age,” as Heroes, Heroines, and History dubbed it, to its position as a mainstay of ’70s and ’80s families through its iconic Wishbook catalogs, Sears now faces complete extinction after a less than stellar recent history.
As Faithfull pointed out, neither of Lampert’s stated goals for Sears materialized. The retailer failed to make inroads following the Kmart team-up, continually losing ground to competitors — particularly as e-commerce began making rapid gains, and Walmart and other physical retail giants gobbled up market share.
“Many reasons have been cited for the company’s demise. Critics claim the company made many mistakes and couldn’t keep up with the likes of Walmart and Amazon. This might be true, but Sears taught America how to shop and for that reason, its legacy will no doubt remain intact,” HH&H recounted.
Now, Seritage Growth Properties, a REIT explicitly and solely designed to maximize value from Sears’ locations, stares down the very end of the line for its remaining Sears holdings. Shares have tumbled to $3.33 as of Jan. 2, from a high of $50, and Seritage may now be looking to get out of the game entirely.
“The goal is to sell the remaining Seritage assets as quickly and profitably as possible, but we are also very open to an alternative transaction that could enhance shareholder value,” Adam Metz, CEO of Seritage, told the New York Times.
BrainTrust
Cathy Hotka
Principal, Cathy Hotka & Associates
Allison McCabe
Director Retail Technology, enVista
David Slavick
Co-Founder & Partner, Ascendant Loyalty
Recent Discussions
Discussion Questions
What are some timeless, and timely, lessons that can be gleaned from the retail legacy left by Sears?
Do you think there is any significant value left in the Sears assets held by Seritage? Does the brand hold any residual value?
What was the turning point for Sears, from industry leader to what little remains?
Poll
Loading …
Sears didn’t die…it was murdered. The lesson I take away from this is that once an enterprise stops looking ahead, it falls behind quickly. What a shame.
Mic drop. Nothing else to say.
Sears’ fall from retail leadership is one of the great cautionary tales in modern commerce — a story that feels eerily like Dr. Ian Malcolm’s line in Jurassic Park: “your scientists were so preoccupied with whether or not they could that they didn’t stop to think if they should.” For decades, Sears dominated U.S. retail by pioneering the mail-order catalog and building a massive network of stores, private brands like Craftsman and Kenmore, and consumer credit services. But as shopping preferences evolved — particularly with the rise of e-commerce — Sears failed to evolve its business to meet those changing behaviors. It discontinued its iconic catalog in 1993, just as the internet was emerging as the next frontier of remote shopping, and never built the kind of digital-first infrastructure that could have carried its brand into the 21st century. That retreat from innovation, combined with underinvestment in store experience and misguided strategic decisions, left Sears unable to compete with both digital natives and more nimble brick-and-mortar rivals.
As for Seritage and residual value, the picture is complex. Seritage Growth Properties was created in 2015 to unlock value from Sears’ real estate, but by the time the strategy was underway, the retailer itself was too far down the decline curve and store closures eroded much of the income base Seritage counted on. Today most of its leased properties are no longer tied to Sears, and Seritage is offloading assets, highlighting that the real estate value had to be monetized outside of the original retail engine that once anchored it. While some parcels may still have development value, the idea that Sears’ former footprint could magically revive the brand ignores the core issue — relevance to the consumer. The brand itself holds only residual nostalgia value at this point; unless resurrected with a radically new value proposition and execution model, the Sears name alone won’t drive meaningful retail demand in today’s competitive marketplace.
The turning point for Sears’ slide from industry leader to near-extinction wasn’t a single event so much as a series of strategic missteps and failures to adapt. The company’s reluctance to fully embrace the shift toward digital shopping and omnichannel experiences, its treatment of stores as liabilities rather than assets, and overly financialized leadership decisions — including asset sales and spin-offs that weakened its operating base — all contributed to a progressive erosion of relevance. By the time Sears finally filed for Chapter 11 in 2018 with billions in losses, it had lost its connection with how consumers wanted to shop and what they expected from a modern retail experience. Retailing is a relentless exercise in meeting the evolving preferences of consumers, and Sears’ inability to do so ultimately sealed its fate — a lesson for every retailer that complacency breeds obsolescence. As a Chicago native and a life-long retailer, this story “hurts my heart.”
The timeless lesson is simple: you’re never too big to fail.
A simple cautionary tale – if you overleverage, your ability to quickly pivot and correctly merchandise your store is severely limited. If you do this for 3 decades, you’ve dug your own grave.
If you own property that once was the crown jewel of the neighborhood and over 30 years that physical location goes to ruin what do you have? Real estate mismanagement and 100% reluctance to evolve, invest, innovate you get what you deserve. Very sad. When I joined in 2008 4,100 stores, $55B sales and stock traded at $120 on NYSE. We did our very best teamed w brilliant leaders and contract partners. Shop Your Way Rewards was voted best in the world in 2011 having amassed 150,000,000 active members. Kept the chain afloat for many years!
If you stand still, you’ll get run over. (especially while looking behind you)
Sears’ retail legacy still holds insights around successful merchandising, branding and customer loyalty. A few:
- Customers trust retailers who explain the value equation in a way they understand. Sears’ own “Good, Better, Best” program communicated an easy to understand decision tree on hundreds of products around quality and price.
- Invest in your own-label products with purpose and criteria. Only put your name on products you really believe in and stand by. Craftsman Tools and Kenmore were built to last with confidence building guarantees.
- Democratize and build trust in unseen products through visuals. The visually pleasing catalogue made it easy for customers to imagine them having and using the products. And the Wish Book created an emotional bond for generations.
Ultimately Sears created their own avalanche (among many other things) by getting complacent and not disrupting their own successful model before competitors did. By the time a hedge fund manager bought it to run and fleece the assets, that was the nail in the coffin.
Much has been written about the demise of Sears that it’s difficult to add any new context now. That said, not only did Sears watch the retail world pass it by for decades while doing little to nothing to adapt their retail business, they were also led to slaughter by leadership that knew little about retail, but had dollar signs in their eyes over the real estate Sears had amassed. When the narrative was more about unlocking value from real estate to “enhance shareholder value” you knew that the retail business had nothing to offer. When did you hear a statement from Eddie Lampert that referred to retail operations? Essentially, never. The lesson to be learned is that once a large retailer is taken over by a real estate and financial leader with little to no retail experience, you know the end is near. It may be a slow death march, but it’s a death nonetheless.
Sears was already in trouble when Lampert took it over. If it weren’t, he would not have been able to get control of it. There was never an objective to revive Sears. The only purpose was to drain its assets—the objective from Day 1.
The customers and employees hoping merchandising and retail operations would improve never stood a chance in this debacle. Would have been better off shutting the doors early and quickly selling off the real estate and assets for everyone involved.
Sears’ story ended well before Lampert took over. It was a classic case study of a large, successful company that failed to see the future. If you are interested, compare the DJI members in 1950 with those today. The Sears story applies to most.
Sears suffered from self inflicted wounds over time as it stopped being an innovative retailer and turned into a real estate holding company. It is an object lesson to all retailers that maximizing short term financial performance through asset management is a road to failure with no return
Sears was more than the sum of it’s parts, servicing many consumers who had limited access to merchandise, until the customer was lost in the shuffle. Greed eroded any and all trust with the consumer. Then Sears collapsed under its own weight.
The single lesson is that retailers should be run as retailers – not as financial or real estate playthings. If the retail core is solid, then it is reasonable to engage in secondary activities. But when those ancillary things become the primary purpose, it is a recipe for disaster.
The lesson is good for any business. Change is consistent. Keep up with it. Customers’ preferences and expectations evolve over time and can be influenced by new, forward-thinking competitors (think Amazon vs. Sears). If you know your customers, listen to your customers, and adapt based on what you learn from them, you will find yourself changing and evolving to keep up with “modern retail.”
More Discussions
Did Holiday 2025 Mark a Shift Into the ‘Agentic Shopping’ Retail Era?
Salesforce data suggests that holiday 2025 was the retail period in which agentic shopping turned the…Should Facial Recognition for Theft Get Another Look?
Retailers and consumers are hotly debating facial recognition tech: theft deterrent, privacy overstepping, or both?Will Retail Bifurcation Persist (or Intensify) in 2026?
Recent Placer.ai data indicated a deepening divide within retail, at least pertaining to foot traffic.
Sears didn’t die…it was murdered. The lesson I take away from this is that once an enterprise stops looking ahead, it falls behind quickly. What a shame.
Mic drop. Nothing else to say.
Sears’ fall from retail leadership is one of the great cautionary tales in modern commerce — a story that feels eerily like Dr. Ian Malcolm’s line in Jurassic Park: “your scientists were so preoccupied with whether or not they could that they didn’t stop to think if they should.” For decades, Sears dominated U.S. retail by pioneering the mail-order catalog and building a massive network of stores, private brands like Craftsman and Kenmore, and consumer credit services. But as shopping preferences evolved — particularly with the rise of e-commerce — Sears failed to evolve its business to meet those changing behaviors. It discontinued its iconic catalog in 1993, just as the internet was emerging as the next frontier of remote shopping, and never built the kind of digital-first infrastructure that could have carried its brand into the 21st century. That retreat from innovation, combined with underinvestment in store experience and misguided strategic decisions, left Sears unable to compete with both digital natives and more nimble brick-and-mortar rivals.
As for Seritage and residual value, the picture is complex. Seritage Growth Properties was created in 2015 to unlock value from Sears’ real estate, but by the time the strategy was underway, the retailer itself was too far down the decline curve and store closures eroded much of the income base Seritage counted on. Today most of its leased properties are no longer tied to Sears, and Seritage is offloading assets, highlighting that the real estate value had to be monetized outside of the original retail engine that once anchored it. While some parcels may still have development value, the idea that Sears’ former footprint could magically revive the brand ignores the core issue — relevance to the consumer. The brand itself holds only residual nostalgia value at this point; unless resurrected with a radically new value proposition and execution model, the Sears name alone won’t drive meaningful retail demand in today’s competitive marketplace.
The turning point for Sears’ slide from industry leader to near-extinction wasn’t a single event so much as a series of strategic missteps and failures to adapt. The company’s reluctance to fully embrace the shift toward digital shopping and omnichannel experiences, its treatment of stores as liabilities rather than assets, and overly financialized leadership decisions — including asset sales and spin-offs that weakened its operating base — all contributed to a progressive erosion of relevance. By the time Sears finally filed for Chapter 11 in 2018 with billions in losses, it had lost its connection with how consumers wanted to shop and what they expected from a modern retail experience. Retailing is a relentless exercise in meeting the evolving preferences of consumers, and Sears’ inability to do so ultimately sealed its fate — a lesson for every retailer that complacency breeds obsolescence. As a Chicago native and a life-long retailer, this story “hurts my heart.”
The timeless lesson is simple: you’re never too big to fail.
A simple cautionary tale – if you overleverage, your ability to quickly pivot and correctly merchandise your store is severely limited. If you do this for 3 decades, you’ve dug your own grave.
If you own property that once was the crown jewel of the neighborhood and over 30 years that physical location goes to ruin what do you have? Real estate mismanagement and 100% reluctance to evolve, invest, innovate you get what you deserve. Very sad. When I joined in 2008 4,100 stores, $55B sales and stock traded at $120 on NYSE. We did our very best teamed w brilliant leaders and contract partners. Shop Your Way Rewards was voted best in the world in 2011 having amassed 150,000,000 active members. Kept the chain afloat for many years!
If you stand still, you’ll get run over. (especially while looking behind you)
Sears’ retail legacy still holds insights around successful merchandising, branding and customer loyalty. A few:
Ultimately Sears created their own avalanche (among many other things) by getting complacent and not disrupting their own successful model before competitors did. By the time a hedge fund manager bought it to run and fleece the assets, that was the nail in the coffin.
Much has been written about the demise of Sears that it’s difficult to add any new context now. That said, not only did Sears watch the retail world pass it by for decades while doing little to nothing to adapt their retail business, they were also led to slaughter by leadership that knew little about retail, but had dollar signs in their eyes over the real estate Sears had amassed. When the narrative was more about unlocking value from real estate to “enhance shareholder value” you knew that the retail business had nothing to offer. When did you hear a statement from Eddie Lampert that referred to retail operations? Essentially, never. The lesson to be learned is that once a large retailer is taken over by a real estate and financial leader with little to no retail experience, you know the end is near. It may be a slow death march, but it’s a death nonetheless.
Sears was already in trouble when Lampert took it over. If it weren’t, he would not have been able to get control of it. There was never an objective to revive Sears. The only purpose was to drain its assets—the objective from Day 1.
The customers and employees hoping merchandising and retail operations would improve never stood a chance in this debacle. Would have been better off shutting the doors early and quickly selling off the real estate and assets for everyone involved.
Sears’ story ended well before Lampert took over. It was a classic case study of a large, successful company that failed to see the future. If you are interested, compare the DJI members in 1950 with those today. The Sears story applies to most.
Sears suffered from self inflicted wounds over time as it stopped being an innovative retailer and turned into a real estate holding company. It is an object lesson to all retailers that maximizing short term financial performance through asset management is a road to failure with no return
Sears was more than the sum of it’s parts, servicing many consumers who had limited access to merchandise, until the customer was lost in the shuffle. Greed eroded any and all trust with the consumer. Then Sears collapsed under its own weight.
The single lesson is that retailers should be run as retailers – not as financial or real estate playthings. If the retail core is solid, then it is reasonable to engage in secondary activities. But when those ancillary things become the primary purpose, it is a recipe for disaster.
The lesson is good for any business. Change is consistent. Keep up with it. Customers’ preferences and expectations evolve over time and can be influenced by new, forward-thinking competitors (think Amazon vs. Sears). If you know your customers, listen to your customers, and adapt based on what you learn from them, you will find yourself changing and evolving to keep up with “modern retail.”