Sears failed to evolve in a changing economy

Sears filed for Chapter 11 bankruptcy in 2018

Although the retailer may have failed financially speaking, some argue that longevity in itself is a success—the brand operated for over 130 years before that bankruptcy filing, after all.

Inside one of the last Sears stores in the US

Sears was once one of the most successful businesses in the US. Today, there aren’t many Sears stores left in the nation, and the ones that are still around feel more like ghost towns than meccas of retail history.

Explore a Sears historical timeline

Sears has existed for over 130 years, and is remembered for much more than its 2018 bankruptcy, from the Sears and Roebuck’s catalog to Discover Card and Allstate Insurance.

Former Sears CEO and hedge fund manager Eddie Lampert was a reclusive billionaire who was once kidnapped from his home in Greenwich, Connecticut by criminals looking to get rich.

Multiple business choices may have hindered Sears’ financial success

There’s no shortage of potential culprits for Sears’ death, from hedge fund manager Eddie Lampert, to Amazon, to the 2008 stock market crash.

Scroll through a Sears historical timeline, starting in the year 1886

The Sears story starts with railroad worker Richard Sears purchasing a declined shipment of watches for a discounted price. An interactive historical timeline chronicles the history of Sears from then onwards.

See America's top companies by revenue in 1994 versus 2023—Sears isn't on the 2023 list, while Amazon isn't in the 1994 edition.

Sears once tried to become a tech company

In 1984, Sears arguably created one of the first online retail services, called “Prodigy,” in 1984 alongside IBM and CBS. But it was more of a WeChat than an Amazon, offering a variety of other services to users a few years before the dot com era.

Sears used to sell entire DIY houses in its catalog

From 1908 through the 1940s, Sears sold DIY house kits starting at $600. An estimated 100,000 homes were built, but fewer than 5,000 have been identified today.

How Sears helped create Discover Card

Sears owned the financial services company Dean Witter, which rolled out the Discover Card in 1986. The Discover Card is just one of many Sears inventions that seems to have outlasted Sears’ peak popularity, including Allstate Insurance and the clothing brand Lands End.

The Sears catalog sold some weird products before it folded, including drugs

At various times in its existence, the Sears catalog sold everything from heroin to tombstones. But by the 2000s, the catalog was no longer in publication.

A private equity firm led the leveraged buyout of Toys 'R' Us before the company's bankruptcy

After being acquired by two private equity firms and a real estate company for more than $6B in 2005, Toys 'R' Us filed for bankruptcy in 2017. Many point to the $400M a year the company had to pay to service its debt, as well as increased competition from online retailers like Amazon, for draining its profits and ultimately dragging it under.

Some argue the Sears catalog undermined Jim Crow laws in the rural South

When the Sears catalog was popularized, Black Americans didn’t always have an easy time shopping in US stores due to racism and Jim Crow laws. Some say that the Sears catalog was radical at the time for helping Black Americans avoid retail shopping in the South—often a negative experience.

There's a group of people hunting down the remaining Sears and Roebuck homes, the DIY houses built from kits Sears once sold in its famous catalog.

Claire's has filed for bankruptcy multiple times

Between competition from online retailers such as Shein and Temu, and too many physical stores for today's retail climate, Claire's has had a difficult time modernizing.

Explore Sears’ holiday Wish Book catalogs dating back to 1930

The Sears Wish Book was a holiday-themed version of its catalogs that helped people make Christmas gift wish lists and more from the 1930s until the early 2000s. See what they looked like with editions in this archive.

There's a group of people hunting down remaining Sears and Roebuck homes

This podcast episode dives into the history of Sears and Roebuck houses, including the people searching for these real estate relics today. Many of them were destroyed or renovated beyond recognition, so they're not easy to find or identify.

Sears and Roebuck once sold DIY house kits

Between 1908 and 1940, "kit homes" that buyers could build themselves were advertised in Sears’ famous catalog—and many of them are still standing today.

North American department store retail groups report sales declined from 2018 to 2023

That's according to a recent report from Bain & Company that dives into consumer sentiment around department store shopping and explores a potential reset for the industry.

Investment banking giant Lehman Brothers filed for bankruptcy in September 2008 when it had $619B in debt, making it the largest bankruptcy ever in the US

Nearly all of its 26,000 employees immediately lost their jobs. But in London, a few hundred remained tucked away, working for another decade to wind down the bank’s European business.

Even iconic companies can get dropped from the Dow

The Dow’s lineup evolves as the economy changes. General Electric, part of the original 1896 index, was removed in 2018, after 122 years. ExxonMobil, once the world’s largest company, was replaced by Salesforce in 2020.

The Sears Tower was the world’s tallest building for about 25 years

Originally constructed in 1970, the Sears Tower in Chicago was later renamed the Willis Tower shortly after Sears headquarters moved out of the building.

In 2006, Macy's was worth $20B—but as of 2024, its market cap was just under $5B

Macy's went from roughly 800 to 500 stores within the same time period. Macy’s has spent the recent years since the pandemic closing swaths of stores.

Every year, nearly 500,000 bankruptcies are filed in the US.

See which companies folded and which survived the dot-com crash

Companies that primarily used the web as a platform for doing business were more vulnerable than companies that created technology. While hardware and software companies managed to make it to the other side, most e-commerce companies took a brutal beating and share prices plummeted.

As of 2024, Macy’s wanted to monetize its store closures through real estate deals

In a 2024 earnings call, Macy’s noted that while it’s remodeling and investing in some of its brick-and-mortar locations, it seeks to shutter other stores in lower-performing locations. It’s estimated that Macy's will close 150 locations through 2026.

Why did WeWork fail and why it's still around

Once valued at $47B, WeWork promised to revolutionize office space—but rapid expansion, financial red flags, and a pandemic-driven shift in work culture led to its 2023 bankruptcy. This overview looks at its rise and fall, and what’s next for the coworking giant.

In 1994, Amazon was founded as an online bookseller

Books were just the start, as founder Jeff Bezos' ultimate goal was to create an "everything store," using the internet to transcend the physical limitations of brick-and-mortar retail. The Seattle-based Amazon gradually added CDs and consumer electronics, becoming a dominant e-commerce player in the late 1990s, and one of the few dot-com companies to make it through the bust.

Macy’s announced a series of pandemic-era store closures in January 2021

Specifically, as mall foot traffic declined, Macy’s sought to grow elsewhere (as did many other retailers around the same time).

Walmart has historically been one of Amazon's largest competitors

While Walmart has been America's largest retailer by revenue for over three decades, Amazon is now fighting for the title, seeking retail supremacy. In this podcast episode from the Wall Street Journal, Sarah Nassauer explores the efforts Walmart has taken to keep its crown.

Red Lobster lost $11M on endless shrimp promotions—but its real estate holdings were what dragged it to bankruptcy

Golden Gate Capital, a PE firm, bought Red Lobster in 2014 for $2.1B. Golden Gate then sold Red Lobster's real estate, more than 500 storefronts, which generated $1.5B in revenue and helped finance the PE firm's acquisition of the company. Analysts say increased debt, high rent costs, and low equity put Red Lobster in an impossible position, leading to its 2024 bankruptcy filing—although the shrimp bill probably didn't help.

After making its US debut in 2015, Shein's sales surged during the pandemic—in 2023, the fast fashion company was valued at roughly $66B.

The Failure Museum is a curated collection of over 1,000 items representing failed products and companies

Sean Jacobsohn, a tech investor and founder of the Failure Museum, uses items from failed businesses to explain the six primary forces behind their flops, from a Theranos mug to a Blockbuster membership card.

In 1965, Warren Buffett took over Berkshire Hathaway, a failing textile company

After buying bulks of its stock, Buffett then flipped Berkshire Hathaway into the most successful and largest holding company in the world, which owns companies like Geico, Duracell, and Fruit of the Loom.

Pets.com is one of the most emblematic dot-com companies

Pets.com—an e-commerce pet store webpage—is a prime example of dot-com companies burning through investments. Despite being a popular and well-known brand, the company struggled to generate enough revenue to become profitable. After raising approximately $82.5M in its February 2000 initial public offering, Pets.com filed for bankruptcy in November of that same year.

GE’s removal marked the end of an era for the Dow

General Electric, the last surviving original Dow component, was dropped in 2018, after years of decline. Its exit symbolized the fading dominance of industrial giants and the index’s shift toward technology and healthcare.

Samsung makes much more than smartphones

Samsung is best known for its highly popular smartphones and related consumer electronics. But the business, first created in 1938, is a conglomerate invested in container shipping, tank building, and even real estate construction like the Burj Khalifa. Its annual $200B in revenue comprises 20% of South Korea's gross domestic product. Watch this video for more on this diverse, enormous company.

11,000 new US dollar stores opened between 2007 and 2017

Dollar store retailers experienced significant fiscal gains during the 2010s, which were then accelerated by the COVID-19 pandemic. But in recent years, dollar stores have been closing in large numbers and suffering financial hardship. Experts point to Walmart's strategy of decreasing prices to cater to inflation-fatigued customers, and point out that when Walmart does well financially, dollar stores typically suffer.

In 2025, Weight Watchers filed for Chapter 11 bankruptcy after reporting revenue and profit losses for multiple consecutive years, with its stock price losing about 99% of its value between 2018 and 2025.

Amazon's success is attributable, in large part, to founder Jeff Bezos’ vision

Bezos parlayed a career on Wall Street into founding an online bookstore that would evolve into the largest online retailer in the world. Bezos’ story is characterized by his relentless focus on innovation and on the customer experience at Amazon.

Sophia Amoruso's company Nasty Gal was worth $100M at its peak

In 2006, Sophia Amoruso started an eBay shop that would later transform into the clothing company Nasty Gal. However, Amoruso’s rags-to-riches success with Nasty Gal didn’t last. After multiple rounds of layoffs and employee complaints, the company filed for bankruptcy in 2016.

Before Lehman Brothers filed for bankruptcy in 2008 with more than $600B in debt, the Federal Reserve tried to orchestrate a private deal to save the then-fourth-largest investment bank in the US.

Bezos has frequently cited a 1999 article titled Amazon.bomb to illustrate how dire the early predictions about Amazon got

Over the years, Amazon founder Jeff Bezos often recalls how wrong the predictions in the 1999 Barron’s cover story were. Among other things, that article declared Amazon’s entire business model to be unsustainable and destined to fail, noting its lack of profit and dependence on a massive amount of capital to fund its growth.

IPOs that failed

Plenty of private companies fail once they try to go public. Failing can mean shares sell for less than their initial asking price on its IPO date, or it can look like a company pulling out of the IPO process at the last minute. Some companies with failed IPOs include Pets.com, Etsy, and Robinhood. Learn more about these companies and others here.

Starbucks operates more than 38,000 stores on six continents

The brand started with a single Seattle cafe and grew into an international sensation, thanks to former CEO Howard Schulz’s bold move toward “reigniting the emotional attachment with customers” rather than focusing on expansion.

WeWork, once a unicorn, declared bankruptcy in 2023

This podcast episode chronicles the complete rise and fall of WeWork—from its founding in 2010 to its eventual 2023 bankruptcy.

The main bank serving Silicon Valley startups and venture capitalists collapsed in 2023

Silicon Valley Bank—the 16th largest bank in the US—served many tech startups in the area as well as many venture capitalists. The bank collapsed in 2023—in a single day, bankers took out $42B.

Walmart was the first traditional retailer to crack the $1T club

In early 2026, the company joined major tech companies Nvidia, Apple, and Meta (among others) as one of the rare firms with a market capitalization beyond $1T. See the latest top companies here.

23andMe declared bankruptcy in March 2025

The consumer genetic testing company, which offered detailed genetic profiles from users' saliva samples, suffered financially after they suffered a major data breach affecting almost 7 million customers in 2023. Its flagship product was a one-time genetic analysis which also made retention of users challenging.

See the growth of US consumer debt

Americans reached an all-time high debt burden in 2024. Data compiled from The Kaplan Group shows the evolution of auto loans, mortgages, credit card debt, and student loans from 2003 to 2023, and finds that after a brief decline after 2008, the total debt burden grew rapidly.