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The Greatest Trades of All Time: A Journey Through the World’s Most Notorious Investment Successes


© Finbold
© Finbold

In the world of finance, there are trades that are remembered not just for their returns, but for the audacity, timing, and brilliance with which they were executed. Some of these trades were a result of meticulous planning, others of pure intuition, and some were simply lucky breaks. But regardless of how they happened, each of these trades left an indelible mark on the financial world. In this article, we’ll look at some of the greatest trades of all time—trades that turned ordinary investors into legends, reshaped markets, and in some cases, even changed the course of history.


1. George Soros and the British Pound: "The Trade of the Century"


Arguably one of the most famous trades in history, George Soros' shorting of the British pound in 1992 is known as "The Trade of the Century." Soros, the founder of Quantum Fund, made a bold bet against the pound, predicting that the UK would be forced to devalue its currency after joining the European Exchange Rate Mechanism (ERM).


The Trade:


Soros’ fund amassed a position of around $10 billion in shorting the British pound. On Black Wednesday, September 16, 1992, the UK government was unable to defend the pound’s value against the Deutsche Mark, as speculators—including Soros—had anticipated. The Bank of England was forced to withdraw the pound from the ERM, devaluing it by 15% overnight.


The Outcome:


Soros made a profit of $1 billion in a single day, and his reputation as one of the greatest investors of all time was solidified. This trade is often cited as an example of successful macroeconomic speculation, showing the immense power of currency movements and the potential for massive profits when a market turns in your favour.


2. Jesse Livermore and the 1929 Stock Market Crash


Jesse Livermore, often referred to as the "Boy Plunger," was one of the most legendary stock traders of the early 20th century. Livermore made a fortune by short-selling stocks during the 1929 stock market crash, a move that made him one of the few to profit from the devastating downturn that would lead to the Great Depression.


The Trade:


Livermore had been observing the stock market's frothy speculative behaviour and had built up significant short positions in stocks. As the market began to crumble in late 1929, Livermore’s shorts continued to grow in value as the stock market tumbled. He was one of the few who had positioned himself to take advantage of the collapse.


The Outcome:


By the time the market bottomed out in 1932, Livermore had reportedly made $100 million—a massive fortune at the time. His success during the Great Depression cemented his place in the annals of trading history, and his methods and philosophies are still studied by traders today. His story is also a cautionary tale, as he later lost his fortune due to his inability to manage risk and his reliance on speculation.


3. Paul Tudor Jones and the 1987 Stock Market Crash


Paul Tudor Jones is widely regarded as one of the most successful hedge fund managers in history. He is particularly famous for predicting the 1987 stock market crash, a catastrophic event that wiped out 22% of the stock market’s value in a single day, the biggest drop since the Great Depression.


The Trade:


Jones had a strong conviction that the stock market was too overvalued and that a significant correction was imminent. In the months leading up to Black Monday on October 19, 1987, Jones and his firm made large short positions, betting against the market. When the crash finally came, Jones was positioned perfectly, profiting from the massive sell-off.


The Outcome:


Paul Tudor Jones is said to have made $100 million in profits from the trade, cementing his reputation as a market genius. He went on to build Tudor Investment Corp into one of the most successful hedge funds in the world. The 1987 crash trade remains one of the most celebrated trades in the history of Wall Street.


4. The Hunt Brothers and Silver (The Silver Bubble of 1980)


In the late 1970s and early 1980s, the Hunt brothers—Nelson Bunker Hunt and William Herbert Hunt—attempted to corner the silver market, betting that the price of silver would rise substantially.


The Trade:


The Hunt brothers began buying up massive quantities of silver, accumulating between 100 and 200 million ounces of the precious metal. Their goal was to drive up the price of silver by creating artificial scarcity, ultimately attempting to control the market. At its peak, the price of silver skyrocketed from around $6 an ounce in 1979 to nearly $50 an ounce in early 1980.


The Outcome:


While initially successful, the Hunts were eventually unable to sustain their positions. The price of silver collapsed in 1980 when the COMEX (the commodities exchange) changed its margin rules, and the market adjusted to the overvaluation. The Hunts were left with massive losses, and the brothers were forced to declare bankruptcy. Despite their failure, their attempt to corner the silver market remains one of the most audacious and ultimately disastrous trades in history.


5. Carl Icahn and the TWA Takeover


Carl Icahn, a corporate raider and activist investor, has made a career out of identifying undervalued companies and aggressively pursuing changes that would unlock value. One of his most iconic trades came in the 1980s when he took over Trans World Airlines (TWA).


The Trade:


Icahn purchased a significant stake in TWA, which was struggling financially. He then engaged in a bitter battle with the airline's management, ultimately taking control of the company. He sold off parts of the business to generate cash and increased shareholder value, a move that often comes with criticism but also massive rewards for investors like Icahn.


The Outcome:


Icahn eventually sold TWA for a significant profit. His success with TWA demonstrated his expertise in corporate governance and restructuring, and it established him as one of the leading activist investors of his time. Icahn's ability to unlock value in struggling companies is still a key aspect of his investing style today.


6. Michael Burry and the 2008 Housing Market Crash


Michael Burry is best known for his prediction of the 2008 financial crisis and his massive bet against the U.S. housing market. Burry, who was managing Scion Asset Management, saw the warning signs of the subprime mortgage collapse long before it became a crisis.


The Trade:


Burry placed significant short positions on the subprime mortgage market by buying credit default swaps (CDS), essentially betting that the mortgages would fail. His bet was based on his analysis that the housing market was in a massive bubble, with many mortgage lenders extending loans to borrowers who were unlikely to repay them.


The Outcome:


When the housing market collapsed, Burry’s bets paid off. His fund made over $700 million, and he was heralded as one of the few investors who saw the crisis coming. His story was famously told in the book and film The Big Short. Burry’s trade is considered one of the most prescient and profitable bets against a financial system in history.


These trades represent a range of strategies, from speculative shorting to contrarian investing, each demonstrating the potential to make monumental profits. While some of these trades led to massive success, others resulted in dramatic failures, reminding us of the immense risks involved in high-stakes trading. What unites these stories is the boldness and insight that led to their execution, and the willingness to take on the market with intelligence, foresight, and occasionally a bit of luck.


These greatest trades of all time offer valuable lessons in risk management, timing, and the importance of having a deep understanding of market dynamics. Whether they were driven by instinct or research, these trades will forever be remembered as defining moments in the history of finance.


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