When I was a kid, the holiday season started when the Toys R Us catalog appeared in the mail, or perhaps inserted into the Sunday Boston Globe.
That catalog features basically every toy and game we could ask for during the holiday season. Almost every child in the nation has had the same experience, and if you’re lucky, you might visit Toys R Us to make your holiday wish list.
The toy brand was everywhere. It seemed like part of the community that would always be there. However, that did not happen.
Toys R Us died for a variety of reasons. It took on a ton of debt due to a leveraged buyout, which weakened its ability to adapt to a changing retail environment. If the chain had focused on an experimental model, leaned into collectible games that people needed a place to play, and made other changes, it would probably still be a national player today.
instead Toys R Us never developed, and both Walmart and Target carried the toys, often at lower prices. Those giants, along with Amazon, helped the struggling toy chain to its demise by cutting thousands of papers.
A brand that seemed to be loved by every kid, that was once a must-visit store if you needed toys, became irrelevant, cash-strapped, and ended in 2017 after failing to reorganize under a Chapter 11 bankruptcy filing.
Toys R Us was a cautionary tale about retail satisfaction. As a former general manager of a large independent toy store, I can confidently say that a model may have been found to save the chain.
Yes, Target and Walmart drove customers away from the stores I ran, but those chains also ignored expensive hard-to-sell board games and collectible miniatures. If Toys R Us had pivoted, its leveraged buyout made difficult by the cash crunch, there were clear ways it could compete.
Toys R Us, however, was not the only tragedy in American retail. Sears was an even steeper decline as the company dwindled to the sad remnants of America’s largest retailers — essentially Walmart, Target, and the Amazon of its time — clinging to existence.
Sears’ decline from operating nearly 3,000 stores worldwide and being the dominant brand in American retail took time and incredible mismanagement.
In 2018, after it emerged from Chapter 11 bankruptcy, Sears had only 700 stores and approximately 68,000 employees. The chain was about a third of the size it was at its peak, but it was still a major 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 Corp.’s 2018 Form 10‑K filed with the U.S. Securities and Exchange Commission (SEC).
However, as the chain moved away from catalog-based department stores and malls, it 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. “Lost sight of the fact that change is a constant.”
Many trace the beginning of the end to Sears’ 2004 merger with Kmart, but the original 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 gambled on real estate instead of focusing on sales. No senior executive could have stopped the next year”. There is news in the gazette.
Portell told the newspaper, ‘The management mistake Sears made was that they never got to the point where they could stop the free fall.
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GlobalData managing director Neil Saunders was not kind in his assessment of the brand’s failure.
“Sears will now serve as a case study in how not to run a retail operation,” he told CBS. “It also serves as an example that even the most powerful and innovative brands of the time can easily fail in a retail environment where change and evolution are the order of the day.”
Only five Sears stores remain. Shutterstock
Year 1886 : Richard W. Sears sells its first watch that Sears started out as.
Year 1887: Sears forms a partnership with Alvah C. Roebuck, forming Sears, Roebuck and Co. Source: Transform
Year 1893: Sears, Roebuck & Co. Officially appeared and began expanding its mail-order list over the clock. Source: CNBC
Early 1900s: Catalog business expands dramatically; Sears became a staple for rural America through its mail-order service. Source: Transform
Year 1925: Sears opens its first brick-and-mortar retail store (in its mail-order complex in Chicago). Source: CNBC
Year 1927: The launch of the in-house brand Kenmore (appliances) and the renowned appliance brand Craftsman moves Sears beyond just catalogs and general merchandise into a home-goods, appliance and hardware identity. Source: Transform
Mid-20th Century (1940s-1960s): Sears becomes one of the largest and most influential retailers in the United States (thanks to both mail-order and its expanding retail presence).
1973: Construction of the Sears Tower in Chicago is completed; At the time, it became the tallest building in the world – a symbol of Sears’ dominance.
1985: Sears invests in financial services by launching the Discover Card.
1990s: Increasing competition from discount retailers and changing consumer habits begin to erode Sears’ dominance. Its retail model, once centered around catalog and full-line stores, is starting to show signs of strain. Source: CNBC
Early 2000s: Sears tries to diversify and restructure to stay relevant.
2005: Sears attempted a turnaround by merging with Kmart, formed under former Sears Holdings Corp. executives.
2010s (leading up to 2018): years of declining sales, store closings, and underinvestment; Sears fails to adapt quickly enough 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/Chairman Eddie Lampert) buys the remaining Sears assets at auction, including several store leases, forming a transformation to run the remainder.
2019-2021: Progress in closing large stores. In early 2020, dozens more store-locations shutter; Certain categories of end stores close (eg auto centers).
December 2022: Small format “Sears Hometown” stores (which were previously closed) file for Chapter 11 bankruptcy, and all remaining Hometown stores are slated for liquidation.
August 2024: Demolition begins at the old Sears headquarters site (in Hoffman Estates, Illinois), indicating that the demolition was once the corporate headquarters.
August 31, 2025: The last Sears store in Puerto Rico closes, further reducing the chain’s global physical presence.
2024-2025: The company’s footprint shrinks drastically. Only till 2025 five Sears stores in the U.S. remain open Source: CNN
Sears has five remaining stores, and one of them is in jeopardy.
“A standalone store in Coral Gables, Florida, could be demolished to build 1,000 housing units. The other four malls operate – in Braintree, Massachusetts; Concord, California; El Paso, Texas; and Orlando, Florida. All of those malls are owned by Simon Property Group,” Simon Property Group, MNL reported.
According to retail experts, there is almost no chance of the chain making a comeback.
There is no chance the remaining stores will be profitable, said Neil Saunders, managing director of retail at research firm GlobalData.
“Sears was not profitable back in the day when it was a very large company with purchasing power,” he told CNN. “Only a small number of stores are profitable with the idea being for birds.”
Stores may exist only, Saunders suggested, to book an accounting loss for tax purposes.
Mark Cohen, a former Sears Canada executive who previously headed retail studies at Columbia University, blamed management.
“If you’re in retail and you’re trying to sell electric typewriters or videotapes that nobody wants to buy anymore, you’re in for a world of hurt,” Cohen said., who blames Lampert for the store’s current state. “But customers didn’t stop buying circular saws or screwdrivers and hammers or tools. If you’re in retail and you sell things that people want to buy, your success or failure is based entirely on the skills you bring to the table. He had none.”
Related: Costco pulls popular product line from its 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 preferred source by clicking here.
