Sears filed for Chapter 11 bankruptcy in 2018

Sears failed to evolve in a changing economy

At its peak, Sears was the largest retailer in the world, making elite objects accessible to the middle class. But in 2018, the company officially filed for bankruptcy due to massive debt and losses.

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.

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.

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.

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.

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.

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.

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.

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.

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

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 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.

What is Chapter 11 bankruptcy?

While there are multiple types of bankruptcies, Chapter 11 is probably the one you've heard about the most. Technically speaking, Chapter 11 bankruptcy involves a reorganization of a business's assets and debts under court supervision. Companies such as Red Lobster, WeWork, and Party City have all filed for Chapter 11 bankruptcy in recent years. Learn more about it here.

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.

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.

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.

Hooters filed for bankruptcy in March 2025 after being operated by two very distinct operations

For years before that filing, the restaurant group had been operated by two different companies: one owned by private equity, and the other that includes the original founders.

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.

Chapter 7 and Chapter 11 filings can impact common stockholders

Publicly traded companies don’t file for bankruptcy out of nowhere—there are typically warning signs in a stock’s performance, quarterly earnings calls, and US Securities and Exchange Commission filings.

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.

Bankruptcy is a legal way to manage overwhelming debt, whether for individuals, corporations, or even local governments

Chapter 7 is for liquidating personal assets to clear debts, Chapter 13 allows a repayment plan for individuals, and Chapter 11 lets businesses reorganize to stay afloat.

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.

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.

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.

Credit scores seriously suffer when individuals file for bankruptcy, and there’s no easy fix

Those who file for Chapter 7 must wait 10 years before the bankruptcy is removed from their credit report. For Chapter 13, the wait time is seven years.

Congress has the power to enact laws related to bankruptcy, thanks to the US Constitution

It has done just that since 1800. This legislation, which outlines the various types of bankruptcy filings, has evolved over time. The most recent iteration is the Bankruptcy Reform Act of 1978, which introduced Chapter 11 filings in an effort to make the process easier for businesses and individuals.

Tom Petty used bankruptcy to change the music industry after resolving a dispute over how a label was treating him as an artist and self-producing an album that racked up $500K in debt.

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.

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.

The history of bankruptcy in the US dates back to the signing of the Constitution

In 1787, this founding document gave Congress the right to establish nationwide bankruptcy laws. Legislators took advantage of that power in 1800 when they passed the Bankruptcy Act of 1800, the first comprehensive bankruptcy law at the federal level.

The most common types of bankruptcy filings are Chapter 7, Chapter 11, and Chapter 13

However, there are actually six types in practice today. These less-common options can be lifelines for foreign businesses operating in the US, local governments, and farms and fisheries.

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.

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.

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.

Amazon didn't have a profitable quarter until 2001, more than 6 years into its existence

Jeff Bezos, however, took pride in Amazon's early unprofitability, reinvesting the money Amazon made back into its business, prioritizing investment into long-term growth and customer acquisition over short-term gains.

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.

Some people make too much money to file for Chapter 7 bankruptcy

Chapter 7 is the most popular type of filing for individuals needing relief. However, to be eligible, debtors must pass an income means test. At the most basic level, they must prove that their average monthly income over six months is below their state’s median. But there are exceptions.

Steve Jobs saved a nearly bankrupt Apple

Apple nearly went bankrupt in 1997, when the tech company had only three months of operational cash left. Apple's board ousted cofounder Steve Jobs in 1985, but he was brought back as interim CEO to revive the company when Apple purchased Jobs' company, NeXT.

A star investment banker was fired, launching a decade-long court fight

Star bankers are the core of an investment banking firm's business, so when Perella Weinberg let their restructuring guru Mike Kramer go in 2015, he sued, launching a ten-year legal fight.

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.

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.

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.

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.

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.

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.

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.

Filing for Chapter 7 bankruptcy can be complex

Debtors must know whether their liabilities are secured or unsecured and what type of assets they have. They also need to know what a filing can and can’t help them with.

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.

Watch a video that details the full history of Macy's

From the first Macy's Thanksgiving Day Parade to opening its flagship store in Herald Square, Macy's has a long and successful history despite its recent financial troubles.