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.

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.

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.

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.

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

A podcast episode dives into the history of Sears and Roebuck houses, including the people still 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.

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 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.

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.

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 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.

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.

PetSmart and Hilton are among 10 of the most famous leveraged buyouts in history

Some of the most famous leveraged buyout deals include Blackstone's 2007 acquisition of Hilton Hotels, in which Blackstone took the then-public company private and then returned it to the public markets in 2013. A British PE firm bought PetSmart for $9B in 2014—one of the most expensive leveraged buyouts since 2007.

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.

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.

Hear how the Piggly Wiggly grocery store founder attempted to squeeze short sellers by cornering the grocery store's stock

Founded in 1916 in Memphis, TN by Clarence Saunders, Piggly Wiggly was the first modern grocery store with aisles for customers to shop for themselves. In 1922, investors placed short positions, sensing that the stock may be overvalued after several Piggly Wiggly franchises in the Northeast went bankrupt. Saunders attempted to squeeze short sellers by taking out $10M and buying up nearly 99% of all available Piggly Wiggly stock. Ultimately, the fiasco ended with Piggly Wiggly's stock being permanently banned from the New York Stock Exchange and Saunders leaving Piggly Wiggly and filing for bankruptcy.

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.

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).

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

From personal hardships to major corporate collapses like Enron and Bed Bath & Beyond, filing for bankruptcy isn't a quick fix or a “get-out-of-jail-free” card—it’s a complex, structured process offering debt relief or repayment options.

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.

Explore America’s top companies by revenue in 1994 versus 2023

America’s top companies by revenue have changed a lot in the past few decades. Sears, for instance, isn’t on the 2023 list, while Amazon isn’t in the 1994 edition.

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.

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.

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.

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.

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.

How one supplement company cost a short seller $1B

Pershing Square, a hedge fund founded and run by Bill Ackman, put short positions on Herbalife in 2012, because it believed the company was a pyramid scheme. Ackman's longtime rival and legendary investor Carl Icahn began buying Herbalife shares, causing the stock price to rise—ultimately hurting Pershing Square's short position.

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.

In early 2021, GameStop's stock surge brought retail investing into the spotlight

Using platforms like Robinhood, everyday investors became a growing presence in financial markets during the Gamestop short squeeze, revealing the influence retail investors can have on the market.

How ‘vulture’ hedge funds make money

Some hedge funds specialize in snapping up distressed assets, like failing newspaper chains, and further stripping down their operational expenses in a bid to make a profit from the initial capital outlay. Delve into how one secretive firm known for the practice operates—and what’s at stake for the broader economy.

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.

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.

Should companies be owned by their workers?

In the last half-century, so-called private equity has transformed industries by purchasing private companies, cutting costs, loading up debt, and then selling the business at a premium—all at a huge profit to the investors. Workers, on the other hand, are often left with nothing. Listen to how both pro-worker economists and a private equity stalwart are trying to shift ownership to workers—a growing tactic proven to improve worker satisfaction and company value.

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.

Bezos' wealth primarily stems from his Amazon ownership stake

Three decades after founding Amazon, Jeff Bezos has built a sprawling empire of business and financial interests. A chart from Visual Capitalist details his many business interests outside of Amazon, including his ownership of the Washington Post; his private aerospace company, Blue Origin; and his personal stake in companies ranging from Airbnb to Uber and Google.

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.

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.

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.

Private equity firms often use leveraged buyouts to acquire new companies

In a leveraged buyout or "LBO," private equity funds finance acquisitions with debt secured by the target company's assets and cash flows. The PE firm aims to improve operations and leverage the company's profile to pay down debt, thereby increasing equity value.

Cheap debt and relatively minimal regulation have fueled private equity's expansion in recent years.

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.

Tesla short sellers benefited from the company's poor performance in 2025

Tesla was widely considered the most-shorted stock until 2024, despite consistent short-seller losses. Between 2016 and 2020, short sellers reportedly lost more than $11B as Tesla's stock price continued climbing. However, long-held short positions began paying out in 2025 as Musk's foray into politics and his eventual feud with President Trump hurt Tesla's stock performance. In 2025, Tesla short sellers made more than $10B.

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.

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.

Many retail investors exited the stock market after 2008, leading to a drop in individual market participation

That changed thanks to GameStop, federal stimulus checks, and strong corporate results in the first quarter of 2021. This chart plots how much retail investors poured into the market each day, reaching records in early 2023.

See Berkshire Hathaway's current market cap and cash on hand

Warren Buffett's holding company, Berkshire Hathaway, has one of the highest-valued stocks in history due to its collection of successful companies. As of 2024, Berkshire owned companies including Dairy Queen and GEICO.

SoftBank lost billions of dollars on WeWork. Meanwhile, WeWork’s founder walked away a billionaire

In the years leading up to WeWork’s bankruptcy, the tech holding company SoftBank invested roughly $16B into the company.

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.