How one supplement company cost a short seller $1B

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.

Watch the infamous live feud between Bill Ackman and Carl Icahn from 2013 in the fallout of a billion-dollar accusation that Herbalife was a pyramid scheme.

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.

Shorting is a high-risk and expensive investment strategy that hedge funds specialize in

Most investors buy stocks with the expectation that those stocks will be worth more tomorrow than they are today. Short selling, known as “shorting,” a stock is the opposite: The investor is betting the stock will drop in value.

Hear why one short seller thinks short selling is now more important than ever.

How one man placed the first short against the Dutch East India Company

Isaac Le Maire, a Dutch businessman and cofounder of the Dutch East India Company, is said to be history's first short seller, betting against the Dutch East India Company's stock price. Le Maire, who had been fired from the spice trading company over an unclear financial dispute, began spreading false rumours about the company to encourage people to sell their stock in order to tank its value.

Porsche briefly made Volkswagen the most valuable company in the world in 2008

In the wake of the 2008 global financial crisis, hedge funds began placing short positions on German automaker Volkswagen. Around the same time, Porsche began acquiring a majority stake in Volkswagen, which decreased the amount of available shares, or the "stock float." Porsche then announced that it owned more than 74% of the company, prompting short sellers to realize they had placed more short positions than were logistically possible given that less than 6% of the company's shares were available to trade. In what is largely recognized as the biggest short squeeze in history, Porsche made $10B, and hedge funds lost more than $30B.

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.

Many hedge funds use short selling as an alternative investment strategy to offset risk

Hedge funds typically use a "long-short" investment strategy—where funds diversify by investing in a mix of long positions and short positions—to balance risk and maximize profits. Including short positions gives hedge funds some protection against downturns in the market, although the strategy can have uncapped losses for investors.

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."

Some experts and investors think short selling—a strategy in which investors bet that a stock will drop in value—helps keep the market healthy.

Bear raiding is a manipulative tactic to bring a stock price down—and part of why short selling can be controversial

Bear raids occur when short sellers use manipulative tactics—like spreading false rumors or coordinating trades—to artificially drive down a stock's price and profit from short positions. Although bear raids are an illegal form of market manipulation, they can spook investors, prompting large selloffs of shares and causing a company's value to plummet. As a result, investors may be hesitant to invest in the company in the future, creating a feedback loop of stock downturn.

How Jim Chanos used a Wall Street Journal article to uncover Enron's fraud

After seeing an article in the Wall Street Journal about the unclear financials of energy companies, Chanos' firm Kynikos Associates began investigating the finances and accounting of Enron, an American energy corporation that was the seventh-largest company at the time. The firm ended up making $500M on its short positions against Enron.

Retail investors are getting burned by long/short strategies

In the US, many retail investors lack the SEC-mandated status (a high enough net worth, income, and other factors) to directly invest in hedge funds. The regulator considers hedge funds too risky for the masses. Hedge fund-like strategies have emerged as a workaround, despite potential pitfalls.

A short squeeze happens when short sellers increase stock prices by buying shares back quickly

When short sellers realize their positions may be incorrect—usually triggered by increasing share prices—they often try to quickly buy back their shares in order to minimize their total losses. When this happens on a large scale, that buying activity can drastically increase to represent the seemingly high demand for that stock. The result is called a "short squeeze," which refers to short sellers literally being squeezed out of their positions by rising prices.

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 the early 2000s, Warren Buffett invested $1M in an index fund to show that passively managed investments would outperform hedge funds—making the point that actively managed funds are not worth the management fees they charge.

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.

In 2008, the 'Big Short' mastermind Michael Burry made more than $700M.

Who is Michael Burry?

Michael Burry is best known for shorting the mortgage bond market in 2007. Before the Great Recession, the legendary investor’s firm took a stake in GameStop and argued the company was being undervalued in 2019. Learn more about Burry’s historical impact on markets here.

What happens when a hedge fund grows too big, too fast?

Dmitry Balyasny, who heads what has become one of the top US hedge fund firms, got a crash course in finance as a teenager, when he started trading stocks—and started losing money. Balyasny went on to lose a whole lot more money. But, this time, it wasn’t his to lose. To find out more about his firm’s remarkable comeback, read this article.

See a real-time list of the most shorted stocks in the US

Every two weeks, the Nasdaq and New York Stock Exchange release the stocks with the most short positions. Some of the companies with the highest short positions as of early 2026 were Hims & Hers and Groupon.

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.

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

Peloton's founder once said the company 'sells happiness' before a disappointing initial public offering

Ahead of the company's IPO, Peloton founder John Foley told investors that "on the most basic level, Peloton sells happiness." However, the inspirational sentiment didn't stick with investors—the company closed the day of its IPO with stocks trading down 11% from the IPO price. (Some users may experience a paywall.)

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.

WellHub is a startup serving roughly 4 million people in 11 countries, providing broad wellness benefits to employees

Valued at $2.4B in 2025, the company helps workers get gym access and meditation apps, in addition to basic healthcare. Listen to the founder of the company, Cesar Cevalho, explain how he scaled the company with Jeff Berman.

Activist investors use large ownership positions to influence companies

By holding large ownership positions, which often come with leveraged access to a company's board or the ability to force a shareholder vote, activist shareholders can change a company's corporate governance, leadership, and overall direction. Critics argue that activist shareholders hurt companies in the long term by prioritizing short-term higher shareholder returns over sustainability and growth efforts.

Read a primer on Elizabeth Holmes, the disgraced founder of biotech startup Theranos who was sentenced to prison for defrauding investors.

After an estimated $8B in customer funds were lost through a cryptocurrency scheme likened to a Ponzi scheme, FTX founder Sam Bankman-Fried was sentenced to 25 years in prison.

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.

The Heinz Company acquired Weight Watchers for $71M in 1978 before selling the company to private equity firm Artal Luxembourg in 1999 for about $735M—more than 10 times the amount Heinz paid for it.

The controversial 'Peloton Wife' ad from 2019 cost the company more than $1B in market value

The 2019 ad of a man gifting his wife a Peloton exercise bike sparked a wave of controversy, with some calling the ad sexist and fatphobic. The ad's backlash decreased the company's market value by $1.6B.

One $100 investment in the Medallion Fund skyrockets over time

The Medallion Fund, the famously secretive quant fund that invests billions of dollars for the partners and employees of a single firm with a legendary track record, has trounced the market for more than three decades. While its results are an extreme outlier, this visualization showcases the power of compound interest.

How a failed investment bank almost became the name of a whiskey line

In the fallout of the Great Recession of 2008, Barclays bought several assets from the failed investment bank Lehman Brothers in a fire sale and maintained the company's trademark, despite the bank's collapse. Tiger Lily Ventures attempted to launch a whiskey line parodying the name, but the product was rejected in court due to questions over Barclays' maintenance of the trademark.

Hedge funds make money from imposing steep fees on investors, as well as from investment performance

Hedge funds often operate on a "2 and 20" model: Investors pay fund managers a 2% management fee, and the hedge fund keeps 20% of their profits. (The 2% is imposed annually, irrespective of performance.) Hedge funds are known for chasing big returns—and taking big risks to get them. This explainer not only breaks down how they work in detail, but also the strategy first introduced in 1949 that still shapes hedge fund investing today.

Supplement sales soared during the pandemic, alongside growing distrust of the health establishment, amplifying a trend that endures—even when some of the products don't even work.

Soybean oil fraud almost decimated American Express in 1963

A New York commodities trader who had defrauded the American government over uninspected meat for school lunches, Anthony "Tino" De Angelis, used American Express warehouses to sell soybean oil. However, Angelis had actually filled the tanks with water and placed just enough soybean oil on top of the tanks to pass inspection. American Express was liable for many of the tanks and its stock faced a huge downturn, opening the door for a then 33-year-old Warren Buffett to make his first purchase in the company.

Hear what Michael Burry thinks about the possibility of an AI bubble

Since his success shorting subprime mortgage-backed securities in 2008, Burry's positions have often become influential, sparking conversations on platforms like X. In 2025, Burry drew attention for betting against Nvidia and Palantir for being overvalued companies.

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.

'The Fund' exposed culture problems and scandals at Bridgewater Associates

In 2023, Rob Copeland—who covered Bridgewater Associates for The Wall Street Journal for 10 years before moving to The New York Times—wrote a book that drew from interviews, company documents, and meeting recordings. "The Fund" highlighted sexual harassment scandals, a company contract to hire strippers, and a toxic company culture. Dalio has criticized the author for being sensational and a gossip.

The 'Two and Twenty' structure allows hedge funds and private equity firms to earn significant returns

With this structure, firms charge limited partners or "LPs" a 2% management fee for overseeing the fund (assets under management or AUM) and take 20% of the fund's overall profits (carried interest). Many private credit funds also operate under this structure.

Mark Zuckerberg was nearly fired from his own company after refusing to sell Facebook to Yahoo for $1B

In 2006, Yahoo tried to buy Facebook for $1B. Despite enthusiasm from nearly all of Facebook's management team and board (which included PayPal cofounder and famed investor Peter Thiel at the time), then 22-year-old Zuckerberg turned down the offer, insisting that Yahoo undervalued the company and didn't have a clear vision for the future. Zuckerberg has since said he regrets not being clear about his intentions to grow the company with his team before the Yahoo bid, as almost all of the company's management team left after he turned down the offer.

Investors need a 'margin account' to short sell stock

Margin accounts are leveraged accounts through brokerage firms that allow investors to make trades without the full amount of capital on hand. Similar to a secured loan, margin accounts often require some form of collateral and typically have a cap on how much investors can borrow. However, trading with a margin account is much riskier than a traditional investment account. Fees and charged interest are due on margin accounts, regardless of trade performance, meaning it's possible for investors to lose more money than just their initial investment.

Ray Dalio allegedly punched one of his early bosses

Before founding his hedge fund, Dalio traded commodities and futures. In 1974, Dalio allegedly punched one of his departmental bosses, causing him to lose his job at Shearson Hayden Stone. He founded Bridgewater Associates the following year. (Some users may experience a paywall.)

A Saudi Arabian sovereign wealth fund divested from LIV Golf after pumping more than $6B into the PGA's controversial rival

The Saudi Arabian Public Investment Fund was the primary backer of LIV Golf, and at one point held more than 90% of the league's ownership stake. Famous golfers, like the three-time Masters' champion Phil Mickelson, criticized the league for "sportswashing" Saudi Arabia's questionable human rights record.

'The Great Onion Corner:' Hear how short-selling onions ended with a ban on onion futures

In the early 1950s, onion farmer and produce trader Vince Kosuga cornered the onion market, resulting in a 1958 ban on onion futures from Congress. After stockpiling onions and buying onion futures, Kosuga then began shorting them. Then, he released his accumulated surplus of onions, driving the price down to essentially zero, and cashed in his short positions.

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.

More than 400 investors turned Peloton down in its initial funding rounds

Peloton founder John Foley said investors rejected the company's initial funding requests because there was no clear indication of what the market for at-home fitness classes looked like. Ultimately, more than 200 angel investors gave the company its first round of cash. (Some users may experience a paywall.)

Read about why bans on short selling are a controversial policy

Generally, short selling is legal, but regulations often restrict short positions when a stock has experienced a sharp price decline (more than 10% in one day). However, negative feedback loops in times of financial crisis have given short selling a bad reputation. The government has temporarily banned short selling during previous market downturns—like The Great Recession of 2008 and the early months of the COVID-19 pandemic—but experts argue whether those bans actually improved market stability or just distorted prices.