When I was a kid, the holiday season started when the Toys R Us catalog came in the mail, or maybe it was inserted in the Sunday Boston Globe.
The catalog featured virtually every toy and game we could ask for during the holidays. Almost every kid in the country has had the same experience, and if you’re lucky, you might even visit a Toys R Us to make your holiday wish list.
The toy brand was everywhere. It seemed like he was part of the community that would always be there. However, this was not the case.
Toys R Us died for many reasons. It took on a lot of debt from a leveraged buyout that undermined its ability to adapt to a changing retail environment. If the chain had converted to an experiential model, geared toward collectible games that need a place for people to play them, and made other changes, it might still be a national player today.
Instead. Toys R Us never evolved, and Walmart and Target carried toys, often at lower prices. Those giants, along with Amazon, helped the beleaguered toy chain to its death with a thousand paper cuts.
A brand that seemingly every kid loved, which was once a must-visit store if you needed toys, had become irrelevant, cash-strapped, and in 2017 was liquidated after failing to reorganize under a Chapter 11 bankruptcy filing.
Toys R Us has been a cautionary tale about retail complacency. As a former general manager of a large independent toy store, I can credibly say that a model could have been found to save the chain.
Yes, Target and Walmart took customers from the store I ran, but those chains also ignored expensive, harder-to-sell board games and collectible miniatures. If Toys R Us had evolved, which made the cash crunch of the leveraged buyout difficult, there were clearly ways it could have competed.
However, Toys R Us was not the only tragedy of American retail. Sears was an even bigger drop, as the company went from being America’s biggest retailer — essentially the Walmart, Target, and Amazon of its day — to a sad relic clinging to existence.
Sears’ fall from operating about 3,000 stores globally and being the dominant brand in US retail took time and incredible mismanagement.
In 2018, after emerging from Chapter 11 bankruptcy, Sears had just under 700 stores and approximately 68,000 employees. The chain was about a third the size it was at its peak, but it was still a large retailer.
To put things into perspective, Sears’ total revenue fell from $36.1 billion in 2013 to $16.7 billion in 2018, according to Sears Holdings Corporation’s 2018 Form 10-K filed with the U.S. Securities and Exchange Commission (SEC).
Still, the chain, which had shifted from being catalog-based to department stores and malls, stopped innovating, according to former Sears executive Mark Cohen, now director of the retail studies program at Columbia Business School.
“The company has been in a death spiral for over a decade,” Cohen told CBS. “The fact that change is a constant has been lost.”
Many trace the beginning of the end to Sears’ merger with Kmart in 2004, but the underlying decline goes back further than that.
“The combined decline of Sears and Kmart, in terms of sales, is unprecedented,” said AT Kearney analyst Greg Portell. The seeds were planted by poor decision-making in the 1980s, when the company made a real estate play instead of focusing on sales.
“The management mistake that Sears made, in retrospect, was that they never got to a place where they could stop the free fall,” Portell told the newspaper.
More retail:
GlobalData managing director Neil Saunders was not kind in his assessment of the brand’s failure.
“Sears will now act as a case study in how not to run a retail operation,” he told CBS. “It also serves as an example that even the strongest and most cutting-edge brands can easily fail in a retail environment where change and evolution are the order of the day.”
Sears only has five stores left. Shutterstock
1886 : Richard W. Sears sells his first lot of watches which was the beginning of what would become Sears.
1887: Sears partners with Alvah C. Roebuck, forming what becomes Sears, Roebuck and Co. Source: Transformco
1893: Sears, Roebuck & Co. officially comes out and begins expanding its mail-order catalog beyond watches. Source: CNBC
Early 1900s: Catalog business expands dramatically; Sears becomes a staple for rural America through its mail order service. Source: Transformco
1925: Sears opens its first brick-and-mortar retail store (in its Chicago mail-order complex). Source: CNBC
1927: The launch of the in-house brand Kenmore (appliances) and the popular Craftsman tool brand moves Sears toward a home goods, appliance and hardware identity beyond catalogs and general merchandise. Source: Transformco
Mid-20th century (1940-1960): Sears becomes one of the largest and most dominant retailers in the United States (thanks to both mail order and its growing presence).
1973: Construction of the Sears Tower in Chicago is complete; at the time, it became the tallest building in the world—a symbol of Sears’ dominance.
1985: Sears ventures into financial services with the launch of the Discover Card.
the 1990s: Increased competition from discount retailers and changing consumer habits begin to erode Sears’ dominance. Its retail model, once centered on catalog and full-line stores, is beginning to show signs of stress. Source: CNBC
In the early 2000s: Sears is trying to diversify and restructure to stay relevant.
2005: Sears merges with Kmart to attempt a turnaround, forming Sears Holdings Corporation under former Sears executives.
2010s (to 2018): years of declining sales, store closures and underinvestment; Sears is failing to adapt quickly to the growth of e-commerce and changing retail trends.
October 2018: Sears Holdings files for Chapter 11 bankruptcy protection after decades of decline. Source: CNBC
January 2019: Hedge fund ESL Investments (affiliated with former Sears CEO/President Eddie Lampert) buys remaining Sears assets, including many store leases, through auction, forming Transformco to run what’s left.
2019-2021: Massive store closings progress. By early 2020, dozens more store locations are breaking ground; the final stores of certain categories close (eg Auto Centers).
December 2022: The smaller “Sears Hometown” stores (which had been spun off earlier) file for Chapter 11 bankruptcy, and all remaining Hometown stores are slated for liquidation.
August 2024: Demolition begins at the old Sears headquarters (in Hoffman Estates, Illinois), signaling the physical dismantling of what was once the corporate headquarters.
August 31, 2025: The last Sears store in Puerto Rico is closing, further reducing the chain’s global physical presence.
2024-2025: The company’s footprint is shrinking drastically. Only until 2025 five Sears stores remain operational in the US Source: CNN
Sears still has five stores, and one of them is clearly at risk.
“One freestanding store in Coral Gables, Florida, could be demolished to build 1,000 housing units. Four others operate in malls — in Braintree, Massachusetts; Concord, California; El Paso, Texas and Orlando Florida. All of these malls are owned by Simon Property Group, the nation’s largest mall operator,” CNN reported.
The chain has little chance of a comeback, according to retail experts.
There is no chance the remaining stores will be profitable, said Neil Saunders, director of retail at research firm GlobalData.
“Sears was not profitable back when it was a much larger company with buying power,” he told CNN. “The idea that it’s only profitable with a small number of stores is for the birds.”
Stores can exist, Saunders suggested, only to record accounting losses for tax purposes.
Mark Cohen, a former Sears Canada executive who was previously head of retail studies at Columbia University, laid the blame squarely on management.
“If you’re in retail and you’re trying to sell something that nobody wants to buy anymore, like electric typewriters or video cassettes, you’re in a world of hurt,” Cohen said., who blames Lampert for the current state of the store. “But customers haven’t stopped buying circular saws or screwdrivers and hammers or appliances. If you’re in retail and you’re selling things that people want to buy, your success or failure is entirely based on the kind of skill you bring to the table. He had none.”
Related: Costco is pulling a popular product line from warehouse shelves
This story was originally published by TheStreet on November 29, 2025, where it first appeared in the Retail section. Add TheStreet as a favorite source by clicking here.
