A Look at the Best Ever Trades in History - Traders Mastermind (2024)

Table of Contents
Let's look at some of the greatest trades ever made. Table of Contents Key Takeaways Jesse Livermore: The 1929 Market Crash Early career and trading strategies Shorting the market in 1929 Legacy and influence on modern traders Paul Tudor Jones: Profiting from Black Monday Background and trading style Predicting and profiting from Black Monday Lessons learned from Paul Tudor Jones’ success George Soros: Betting Against the British Pound The Quantum Fund and Soros’ investment strategy The trade that broke the Bank of England Impact on currency markets and modern trading Jim Chanos: Exposing Enron's Fraud Background and expertise in short selling Uncovering Enron’s deception The aftermath and lessons for investors John Paulson: Capitalizing on the Subprime Real Estate Crisis Early career and hedge fund success The subprime real estate trade Paulson’s continued market insights and trades Kyle Bass: Profiting from the Housing Collapse Background and investment philosophy The subprime bet and its payoff Lessons for traders from Kyle Bass’ experience Andrew Hall: The Remarkable Oil Trade Background and expertise in energy markets The bold oil trade Impact on oil markets and trading strategies Martin Armstrong: Predicting the 1987 Crash with Precision Background and development of Armstrong’s theories The accurate prediction of the 1987 crash Summary Frequently Asked Questions What is the best trade in history? Who is the most successful trader in history? Which was the most profitable trade? What is the significance of understanding the best trades in history? FAQs

Let's look at some of the greatest trades ever made.

A Look at the Best Ever Trades in History - Traders Mastermind (1)

Home » A Look at the Best Ever Trades in History

Want to learn about the greatest trades ever made?

Good, you’re in the right place…

From Paul Tudor Jonestrading Black Monday, to George Sorosbreaking the bank of England. Let’s explore who traded what, when, why and of course how much they made.

Table of Contents

Key Takeaways

  • Jesse Livermore, Paul Tudor Jones, George Soros, Jim Chanos, John Paulson, Kyle Bass, Andrew Hall, and Martin Armstrong are highlighted as some of the most successful traders in history, with notable trades that include shorting the market during significant downturns and predicting major financial crises.

  • Their legendary trades capitalised on market inefficiencies, advanced understanding of economic indicators, and strategic use of financial instruments such as credit default swaps, demonstrating both high-risk taking and acute market foresight.

  • These traders left a significant impact on trading practices and financial market regulations, reinforcing the importance of risk management, the influence of individual traders on the global financial markets, and the need for transparency in corporate governance.

Jesse Livermore: The 1929 Market Crash

Jesse Livermore, a name that reverberates through the annals of trading history, takes centre stage in our story. Known as the “Great Bear of Wall Street,” Livermore left an indelible mark on the world of trading.

His audacious bets and uncanny market predictions earned him a fortune and a reputation as one of the greatest traders of all time.

Early career and trading strategies

Livermore’s trading journey began at the tender age of 14 when he started working at Paine Weber & Co’s Boston stockbroking offices.

His keen eye for observation and sharp analytical skills led him to develop unique trading strategies that would later shape the course of his career.

At a time when insider trading was rampant and information was a luxury, Livermore used his understanding of bucket shops and critical junctures to time his trades to perfection.

His pioneering strategies in trading were a clear demonstration of his prophetic insight and shrewdness, paving the way for his later accomplishments.

Shorting the market in 1929

Livermore’s crowning achievement came in 1929 with the infamous stock market crash.

While others watched helplessly as their fortunes dwindled, Livermore saw opportunity…

Leveraging his understanding of market dynamics and over-leveraging, he established a short position on corporate stocks. His audacious bet paid off, earning him a profit of over $100 million and cementing his place in trading history.

Legacy and influence on modern traders

Livermore’s legacy extends far beyond his personal fortune.

His innovative trading strategies have shaped the world of trading, influencing countless traders and setting the foundation for modern trading practices.

His use of stop-loss orders and position sizing, his understanding of market psychology, and his emphasis on risk management are testaments to his far-reaching influence.

Of course you can’t really say you’re a trading until you’ve read the classic bookReminiscences of a Stock Operator.

Paul Tudor Jones: Profiting from Black Monday

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Next on our journey isPaul Tudor Jones, a titan of the trading world who made his mark during one of the darkest days in market history –Black Monday.

Jones, a visionary with a knack for spotting market trends, is renowned for turning calamity into opportunity.

Background and trading style

Jones’ journey into the world of trading began under the mentorship of his cousin William Dunavant Jr., a renowned cotton merchant.

With a degree in economics and an unquenchable thirst for success, Jones dived headfirst into the world of commodity trading.

Distinguishing himself from his contemporaries with his unique trading style and ability to identify market trends, Jones set the groundwork for his ensuing triumphs.

Predicting and profiting from Black Monday

The crowning jewel of Jones’ trading career was his prediction and profit from Black Monday.

Using the Elliott Wave Theory and technical analysis, Jones foresaw the devastating market crash that wiped out millions in a single day. But while others reeled from the shock, Jones profited, his prescient prediction earning him a cool $100 million.

Lessons learned from Paul Tudor Jones’ success

Valuable insights can be drawn from Jones’ triumphs. His adeptness at merging historical analysis with current market trends emphasises the necessity for a holistic approach to trading.

His daring investments and inclination towards risk-taking underscore that boldness is often rewarded in the trading world.

George Soros: Betting Against the British Pound

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Our journey takes us next toGeorge Soros.

Known as the “Man Who Broke the Bank of England,” Soros’ audacious bet against the British pound stands as one of the most legendary trades in history.

The Quantum Fund and Soros’ investment strategy

Soros’ accomplishments are a testament to his distinctive investment approach and the innovativeQuantum Fund.

Soros’ strategy was predicated on identifying vulnerabilities in the financial market and exploiting them.

His Quantum Fund, a privately ownedhedge fundwith a global footprint, became a testament to his investment acumen.

The trade that broke the Bank of England

Soros’ audacious bet against the British pound shook the foundations of the financial world.

By identifying the weaknesses in the European Rate Mechanism and leveraging these vulnerabilities, Soros made a fortune while simultaneously causing a financial earthquake in England.

Impact on currency markets and modern trading

Soros’ trade left a lasting impact on the world of trading and the global currency markets.

It highlighted the potential for extensive currency speculation and exposed the weaknesses of national financial institutions.

His audacious bet also brought attention to the potential impact of individual traders on the global financial system.

Jim Chanos: Exposing Enron's Fraud

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Our journey through the world of trading brings us next to Jim Chanos, the man who exposed one of the biggest corporate scandals in history.

Known for his expertise in short selling, Chanos is renowned for his role in exposing thefraudulent accounting practices of Enron.

Background and expertise in short selling

Chanos began his career as a stock operator and analyst, honing his skills in identifying distressed companies. His ability to spot discrepancies and anomalies in financial statements made him a formidable short seller, a role he played to perfection in the Enron scandal.

Uncovering Enron’s deception

Chanos’ meticulous analysis of Enron’s financial statements led him to discover the company’s fraudulent accounting practices. His discovery led to the downfall of one of America’s biggest corporations and exposed the dark underbelly of corporate America.

The aftermath and lessons for investors

The Enron debacle acted as an alarm bell for investors, underscoring the need for transparency and integrity in corporate governance, which is one of the main concerns of the Securities and Exchange Commission.

Chanos’ part in uncovering Enron’s deceit highlights the significance of due diligence and critical scrutiny in investment choices.

John Paulson: Capitalizing on the Subprime Real Estate Crisis

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Our next stop on this journey through trading history brings us to John Paulson, a man who made a fortune by betting against the subprime real estate market. His audacious bet at a time of financial turmoil made him one of the wealthiest men in the world.

Early career and hedge fund success

Paulson’s journey into the world of trading began with a degree in business and a stint at Boston Consulting Group. His analytical skills and keen understanding of market dynamics led him to establish his own hedge fund, Paulson & Co., which would go on to make one of the most profitable trades in history.

As a successful hedge fund manager, Paulson’s expertise has been widely recognised in the industry, placing him among the top hedge fund managers.

The subprime real estate trade

Paulson’s audacious bet against the subprime real estate market was a masterstroke of strategic foresight. Recognising the unsustainable nature of the real estate boom, Paulson capitalised on the impending market crash, turning an initial investment of $110 million into a staggering $700 million.

Paulson’s continued market insights and trades

Paulson’s success in the subprime real estate market is not an isolated event. Continually guided by his sharp grasp of market dynamics and his talent for identifying market inefficiencies, Paulson has established himself as a power player in the trading sphere.

Kyle Bass: Profiting from the Housing Collapse

Kyle Bass is another trader who made a fortune by betting against the housing market. His audacious bet against subprime mortgages earned him a fortune and cemented his place in trading history.

Background and investment philosophy

Bass’ success in trading can be attributed to his unique investment philosophy. A firm believer in the power of market analysis and foresight, Bass has made a name for himself by spotting market inefficiencies and capitalising on them.

The subprime bet and its payoff

Bass’ most audacious bet came during the 2008 financial crisis when he bet against subprime mortgages using credit default swaps. Partnering with an investment bank, his bold move paid off handsomely, turning an initial investment of $110 million into a staggering $700 million.

Lessons for traders from Kyle Bass’ experience

Bass’ triumphant journey provides potent insights for traders. His knack for detecting market inefficiencies and readiness to embrace calculated risks underline that boldness is often rewarded in trading.

Andrew Hall: The Remarkable Oil Trade

Andrew Hall’s audacious oil trade stands as one of the most legendary trades in history. Hall’s bet against the oil market shook the foundations of the financial world and earned him a fortune.

Background and expertise in energy markets

Hall’s journey into the world of trading began with a stint at BP. His keen understanding of the energy markets and his ability to spot market inefficiencies made him a formidable trader, a role he played to perfection in his audacious oil trade.

The bold oil trade

Hall’s audacious oil trade came at a time when the world was reeling from the effects of the global financial crisis. Despite the bleak market conditions, Hall saw an opportunity and made a bold bet against the oil market, a move that paid off handsomely.

Impact on oil markets and trading strategies

Hall’s daring oil trade had a profound and lasting influence on the trading world and the global oil markets. It highlighted the potential for extensive speculation in the oil market and exposed the weaknesses of national oil institutions.

His big bet also brought attention to the potential impact of individual traders on the entire market, particularly in the global oil sector.

Martin Armstrong: Predicting the 1987 Crash with Precision

Our final stop on this journey through trading history brings us to Martin Armstrong, a visionary who predicted the 1987 market crash with uncanny precision. Utilising his distinctiveEconomic Confidence Model, Armstrong anticipated the crash, issued warnings to investors, and cemented his position in the annals of trading.

Background and development of Armstrong’s theories

Armstrong’s journey into the world of trading began with a fascination with patterns and cycles (likeTaylorandWyckoff).

His keen eye for pattern recognition and his understanding of market dynamics led him to develop the Economic Confidence Model, a tool that he used to predict market trends and cycles with remarkable accuracy.

The accurate prediction of the 1987 crash

Armstrong’s crowning achievement came in 1987 when he accurately predicted the market crash. Using the Economic Confidence Model, Armstrong foresaw the crash and warned investors, earning him a place in trading history.

Summary

Our journey through the annals of trading history has brought us face-to-face with the big bets, brilliant strategies, and remarkable foresight of some of the greatest traders in history.

Each of these traders, in their own unique way, has shaped the world of trading and left a lasting legacy.

Their stories serve as a reminder of the power of foresight, the importance of risk management, and the rewards of audacious bets.

Frequently Asked Questions

What is the best trade in history?

The best trade in history is often considered to be George Soros’s shorting of the British Pound in the early 1990s, making over $1 billion. This trade, along with others by notable investors, involved highly leveraged currency exploitation.

Who is the most successful trader in history?

The most successful traders in history include Jesse Livermore, Paul Tudor Jones, Warren Buffett, and Steven Cohen. They are considered to be the richest traders of all time.

Which was the most profitable trade?

It’s probably George Soros again, but Michael Burry also made a damn good trade shorting subprime.

What is the best thing to trade?

None of these great trades were in one specific market. They all were a thesis that played out over time. These traders spotted an opportunity and found the right vehicle to express that trade.

What is the significance of understanding the best trades in history?

Understanding the best trades in history is significant because it offers valuable insights into the successes and failures of past traders, enabling us to learn from their strategies and decisions.

It’s also super inspirational!

Looking for more? Check out theblog,podcastandwebinarsections.

A Look at the Best Ever Trades in History - Traders Mastermind (2024)

FAQs

Who is the most successful trader in history? ›

1. George Soros. George Soros, often referred to as the «Man Who Broke the Bank of England», is an iconic figure in the world of forex trading. His net worth, estimated at around $8 billion, reflects not only his financial success but also his enduring influence on global markets.

What is the 3-5-7 rule in trading? ›

What is the 3 5 7 rule in trading? A risk management principle known as the “3-5-7” rule in trading advises diversifying one's financial holdings to reduce risk. The 3% rule states that you should never risk more than 3% of your whole trading capital on a single deal.

What is the best trade in history? ›

The best trade in history is often considered to be George Soros's shorting of the British Pound in the early 1990s, making over $1 billion. This trade, along with others by notable investors, involved highly leveraged currency exploitation.

What was Jesse Livermore's strategy? ›

Livermore advised investors to buy on a rising market and sell on a down one. Livermore maintained that leading stocks would be the first to break a trading range and reach top prices. Livermore recommended that investors should draw out half of every profit made and set it aside as a reserve.

Who is the billionaire trader? ›

George Soros, the legendary investor and philanthropist, is widely recognized as one of the most successful forex traders in history. In 1992, Soros famously "broke the Bank of England" by shorting the British pound, earning an estimated $1 billion in a single day.

What is 90% rule in trading? ›

Understanding the Rule of 90

According to this rule, 90% of novice traders will experience significant losses within their first 90 days of trading, ultimately wiping out 90% of their initial capital.

What is No 1 rule of trading? ›

Rule 1: Always Use a Trading Plan

You need a trading plan because it can assist you with making coherent trading decisions and define the boundaries of your optimal trade.

What is the 80% rule in trading? ›

If the market can trade back inside value for two consecutive 30 minute periods, then it has an 80% chance of rotating to the other side of value. –Context is extremely important. Do not trade this rule mechanically and expect to have good results.

What trade is the king of all trades? ›

This presentation took place at a feast given by the King to celebrate the event, who, in a well-ordered speech, admitted having been taken in by the tailor's beautiful coat, but now felt the greatest pleasure in announcing that for all time the blacksmith should be regarded as the King of all the trades.

What stock made the most money in history? ›

The Best Performing Stocks in History
  • Coca-Cola. (NASDAQ: KO) ...
  • Altria. (NASDAQ: MO) ...
  • Amazon.com. (NASDAQ: AMZN) ...
  • Celgene. (NASDAQ: CELG) ...
  • Apple. (NASDAQ: AAPL) ...
  • Alphabet. (NASDAQ:GOOG) ...
  • Gilead Sciences. (NASDAQ: GILD) ...
  • Microsoft. (NASDAQ: MSFT)

What is the greatest single trade of all time? ›

George Soros and Stanley Druckenmiller famously broke the Bank of England by shorting the pound in 1992. The day is known as Black Wednesday and the trade not only netted the pair a fortune (around $1 billion) but wrote them into folklore.

What is the gann theory? ›

Gann theory was a concept developed by William D. Gann in the 1900s. He was a successful trader and believed that stock prices change with an angle. An asset can move in different angles. He noticed that price changes were related to natural geometric shapes and predicted future price movements in relation to time.

How did Jesse Livermore manipulate the market? ›

At the bucket shop, Livermore would place a trade on a stock that he knew was only thinly traded on the NYSE. He would then trade the shares on the NYSE to move the actual stock price substantially in the required direction. The new price would come through to the bucket shop and Livermore would collect his profits.

Was Jesse Livermore a trend trader? ›

Jesse did not have the convenience of modern-day charts to graph his price patterns. Instead, the patterns were simply prices that he kept track of in a ledger. He only liked trading in stocks that were moving in a trend, and he avoided ranging markets.

Has anyone got rich from trading? ›

Many people have made millions just by day trading. Some examples are Ross Cameron, Brett N. Steenbarger, etc. But the important thing about day trading is that only a few can make money out of day trading and the rest end up losing their entire capital in day trading.

Who is the greatest investor of all time? ›

Warren Buffett is widely considered the greatest investor in the world. Born in 1930 in Omaha, Nebraska, Buffett began investing at a young age and became the chairman and CEO of Berkshire Hathaway, one of the world's largest and most successful investment firms.

What is the biggest trading profit ever? ›

Probably the greatest single trade in history occurred in the early 1990s when George Soros shorted the British Pound, making over $1 billion on the trade. Most of the greatest trades in history are highly leveraged, currency exploitation trades.

Who is the best trader right now? ›

  1. Paul Tudor Jones (1954–Present) The founder of Tudor Investment Corporation, a $11.2 billion hedge fund, Paul Tudor Jones made his fortune shorting the 1987 stock market crash. ...
  2. George Soros (1930-Present) ...
  3. John Paulson (1955-Present)

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