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, the DIY houses built from kits Sears once sold in its famous catalog.

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.

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 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).

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.

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

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.

GameStop stock began a meteoric rise in January 2021, rallying from a low of $2.57 to as high as $438 when Keith Gill helped mobilize retail investors to drive prices higher

Keith Gill was a financial advisor who posted on social media under usernames including "Roaring Kitty." Backing from Chewy founder Ryan Cohen, who became GameStop's CEO, took things up a notch.

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.

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.

American Express briefly owned Lehman Brothers

In 1984, Shearson, a retail banking company and American Express subsidiary, bought the investment banking company Lehman Brothers—best known for its historic 2008 collapse—for $360M. The businesses were then called Shearson Lehman/American Express. American Express spun off Lehman Brothers with an IPO in 1994 that attracted nearly $3B in new capital.

Amazon founder and billionaire Jeff Bezos' wealth primarily stems from his Amazon ownership stake.

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.

Larry Fink cofounded BlackRock with a $5M investment from Blackstone cofounder Stephen Schwarzman in 1988, before officially severing ties with Blackstone in 1994.

Estée Lauder's son, Leonard Lauder, transformed Estée Lauder into a global powerhouse

Leonard Lauder became president of Estée Lauder Companies in 1972 and is credited with much of the brand's expansion. Under his leadership, the company launched new lines like Aramis and acquired luxury brands to bolster its position in the luxury beauty market.

How to make a billion dollars, with Brad Jacobs

Brad Jacobs is a serial entrepreneur who has launched eight billion-dollar enterprises during his storied financial career. With companies focused in energy, waste, and more, Jacobs has stuck to a roll-up playbook of consolidating small players into one conglomerate within an industry, a common tactic of similar private equity firms. This podcast from Founders summarizes Jacobs' book detailing his approach.

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.

Bezos owned roughly 8% of Amazon as of 2025

Three decades after founding Amazon, Jeff Bezos has built a sprawling empire of businesses and financial interests. Other large stakeholders in the company include Amazon CEO Andrew Jassy and Bezos’ ex-wife MacKenzie Scott. This article provides more details on who owns how much of Amazon.

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.

A landmark hedge fund court case once reshaped high finance

Hedge fund traders tied to insider trading by probing prosecutors are relatively rare. When billionaire hedge fund legend Steve Cohen, founder of SAC Capital, pleaded guilty to trading on inside information, Wall Street trembled. The outcome of the case remains a cautionary tale for traders today.

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.

Family Dollar and Dollar Tree merged in 2015 before splitting in 2025

Dollar Tree completed its acquisition of Family Dollar for about $9B in 2015. However, in 2025, Dollar Tree sold Family Dollar to private equity firms Brigade Capital Management and Macellum Capital Management for just over $1B after Family Dollar lagged in performance.

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.

How a Reddit thread drove GameStop's stock price up and gutted the pockets of short sellers

In 2021, many hedge funds felt like GameStop was overvalued and began placing short positions. However, users in the "r/WallStreetBets" subreddit felt like the hedge funds were too aggressive in their short positions and rallied together to purchase large amounts of GameStop stock, pushing the stock price up. As the stock price rose, hedge funds began buying back their shares to cover their short positions, which also began pushing the stock price up in what's called a "short squeeze."

In 2012, Bill Ackman's hedge fund, Pershing Square, took a $1B short position against supplement company Herbalife after discovering that 82% of the company's distributors never made a profit, calling it a true pyramid scheme.

A deep dive into Enron, one of the largest accounting scandals in history

Investing comes with great opportunities for reward, but it also carries great risk. Investors learned that the hard way when Enron collapsed. Everyone lost money—from the largest institutions on Wall Street to mom-and-pop investors who bought S&P 500 index funds. This series from American Scandal starts with a close-up into an investment manager at Enron who started to unravel the accounting scandal happening behind the scenes. Listen here.

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.

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

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.

Listen to Keith Gill's testimony from the GameStop hearing

"I am not a cat, I am not an institutional investor, nor am I a hedge fund." That's how Keith Gill, aka Roaring Kitty, kicked off his testimony before Congress on the wild trading action in GameStop stock. Lawmakers took notice of the meme stock craze, and the collapse of hedge fund Melvin Capital, opening up an investigation into what exactly moved so much money.