Greatest Individual Financial Trades Ever!

Long before Reddit users banded together to short squeeze GameStop into Billions of dollars, there have been some gutsy and huge wins in the markets.

For all the winners there are losers, but for everyone that plays the markets it is very intriguing to hear those that had off the chart successes.

Sit down in case you get light headed and enjoy these instances of obscene financial wins. Scroll through with the NEXT button at the bottom of each page.

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Ryan Cohen - Over $1 Billion for GameStop Investment!

Ryan Cohen (born 1985 or 1986) is the co-founder and former CEO of e-commerce company Chewy, which was acquired by PetSmart in 2017 for $3.35 billion.

Following the sale of Chewy, Cohen made a significant investment in Apple, making him the largest individual shareholder of the tech company with 1.55 million shares (6.2 million split-adjusted shares as of August 31, 2020).

In September 2020, Cohen disclosed a near 10% stake in GameStop, an American video-game retailer, making him the company's biggest individual investor. This was later increased to 12.9% on December 17, 2020 through an amended 13D filing with SEC. According to these filings, Cohen’s firm, RC Ventures, has expressed willingness to get more involved with the company in order “to produce the best results for all shareholders." [1]

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Bill Ackman - $2.6 Billion on Coronavirus Recovery

William Albert Ackman (born May 11, 1966) is an American investor and hedge fund manager. He is the founder and CEO of Pershing Square Capital Management, a hedge fund management company. Ackman is considered by some to be a contrarian investor but considers himself an activist investor.

Ahead of the 2020 stock market crash, Ackman hedged Pershing Square's portfolio, risking $27 million to purchase credit protection, insuring the portfolio against steep market losses. The hedge was effective, generating $2.6 billion in less than one month.

On March 18, 2020, in an emotional interview with CNBC, Ackman called upon President Trump for a "30-day shut down" of the American economy to slow the spread of coronavirus and minimize loss of life and ensuing economic destruction resulting from the shutdown. Ackman warned that without intervention, hotel stocks were “going to zero” and said that America could “end as we know it." He also cautioned U.S. companies to stop stock buyback programs because “hell is coming.”

Ackman later received criticism for actively buying discounted equity stakes in the very companies he was warning could fail; however, Ackman already had realized roughly half of the gains before appearing during the CNBC interview. [1]

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George Soros - Profit of $1 Billion Shorting British Currency

George Soros, (born György Schwartz, August 12, 1930) is a Hungarian-born American billionaire investor and philanthropist. As of May 2020, he had a net worth of $8.3 billion.

Soros is known as "The Man Who Broke the Bank of England" because of his short sale of US$10 billion worth of pounds sterling, which made him a profit of $1 billion during the 1992 Black Wednesday UK currency crisis. Based on his early studies of philosophy, Soros formulated the General Theory of Reflexivity for capital markets, which he says renders a clear picture of asset bubbles and fundamental/market value of securities, as well as value discrepancies used for shorting and swapping stocks. [1]

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Jesse Livermore - Shorted 1929 Market for $100 Million

Jesse Lauriston Livermore (July 26, 1877 – November 28, 1940) was an American stock trader. He is considered a pioneer of day trading and was the basis for the main character of Reminiscences of a Stock Operator, a best-selling book by Edwin Lefèvre. At one time, he was one of the richest people in the world; however, at the time of his suicide, he had liabilities greater than his assets.

Some of Livermore's trades, such as taking short positions before the 1906 San Francisco earthquake and just before the Wall Street Crash of 1929 which made him $100 million, are legendary and have led to his being regarded as the greatest trader who ever lived. [1]

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Paul Jones - Made $100 Million Shorting 1987 Market

Paul Tudor Jones II (born September 28, 1954) is an American billionaire hedge fund manager, conservationist and philanthropist. In 1980, he founded his hedge fund, Tudor Investment Corporation, an asset management firm headquartered in Stamford, Connecticut. Eight years later he founded the Robin Hood Foundation, which focuses on poverty reduction.

One of Jones' earliest and major successes was predicting Black Monday in 1987, tripling his money during the event due to large short positions.

In 1987, betting on a crash in the United States stock market Jones' Tudor' returned 125.9 percent after fees, earning an estimated $100 million.

Peter Borish, second-in-command to Jones at Tudor Investment Corporation, anticipated the crash in 1987 by mapping the 1987 market against the market preceding the 1929 crash. [1]

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John Templeton - Shorted Tech Bubble in 2000

Sir John Marks Templeton (29 November 1912 – 8 July 2008) was an American-born British investor, banker, fund manager, and philanthropist. In 1954, he entered the mutual fund market and created the Templeton Growth Fund, which averaged growth over 15% per year for 38 years. A pioneer of emerging market investing in the 1960s, Money magazine named him "arguably the greatest global stock picker of the century" in 1999. [1]

A veteran at making short bets, made his biggest and best bet ever just eight years before he died, in 2000, just before the dot-com bubble popped. He shorted a whole variety basket of internet stocks, said that it was the easiest money he'd ever made. [2]

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Louis Bacon - Correctly Bet Iraq Would Invade Kuwait

Louis Moore Bacon (born July 25, 1956) is an American investor, hedge fund manager, and philanthropist. He is the founder and chief executive of Moore Capital Management.

Forbes Magazine estimates his net worth to be US$1.81 billion, making him the 374th richest person on the Forbes 400 as of February 2017. [1]

Back in the 90s, when the idea of trading on a macro basis was almost unheard of, Bacon beat the CIA in predicting that Hussein would attack Kuwait, went long on oil and short on stocks. His hedge fund returned 86 percent that year.

Bacon's accurate predictions of market events around the Iraq war fetched his hedge fund returns of 35 percent a year for thirteen years. [2]

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David Tepper - $7 Billion Betting on Banks Recovery 2009!

David Alan Tepper (born September 11, 1957) is an American billionaire businessman, hedge fund manager, and philanthropist. He is the owner of the Carolina Panthers of the National Football League (NFL) and Charlotte FC in Major League Soccer (MLS). Tepper is the founder and president of Appaloosa Management, a global hedge fund based in Miami Beach, Florida.

He earned a bachelor's degree in economics from the University of Pittsburgh in 1978, and an MBA from Carnegie Mellon University in 1982. In 2013, he donated his largest gift of $67 million to Carnegie Mellon, whose Tepper School of Business is named after him.

For the 2012 tax year, Institutional Investor's Alpha ranked Tepper's $2.2 billion paycheck as the world's highest for a hedge fund manager. [1]

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Andrew Hall - Long Bet Oil Would Rise From $30 to $100

Andrew Hall is an English hedge fund manager who served as the head of commodities trading firm Phibro LLC and the head of his own hedge fund Astenbeck Capital. In 2019, the Financial Times described him as the "most successful oil trader of his generation.

As the head of a then subsidiary of Citigroup, Hall's compensation drew criticism about Wall Street pay in the aftermath of subprime-related bank bailouts. Citigroup sold Phibro LLC to Los Angeles-based Occidental Capital for $370 million, in part due to the pay controversy. Hall earned about $100 million in 2008. Also in 2018, while still at Citigroup, he launched Astenbeck Capital Management, a hedge fund which raised more than $3.0 billion. [1]

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Kyle Bass - Bet Against Subprime Mortgages for $3-4 Billion

Kyle Bass (born September 7, 1969) is an American hedge fund manager. He is the founder and principal of Hayman Capital Management, L.P., a Dallas-based hedge fund focused on global events.

In 2008, Bass successfully predicted and effectively bet against the U.S. subprime mortgage crisis by purchasing credit default swaps on subprime securities which, in turn, increased in value when the real estate bubble burst. [1]

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Stanley Druckenmiller - Made $1 Billion Betting on the German Mark

Stanley Freeman Druckenmiller (born June 14, 1953) is an American investor, hedge fund manager and philanthropist. He is the former chairman and president of Duquesne Capital, which he founded in 1981. He closed the fund in August 2010 because he felt unable to deliver high returns to his clients. At the time of closing, Duquesne Capital had over $12 billion in assets. [1]

While George Soros was shorting the pound, Stanley Druckenmiller, who was then employed by Soros's Quantum fund, was betting on the German mark. Before the Berlin Wall fell, the reunification of East and West Germany seems like so mammoth a task that the German mark was depressed to an extreme level.

Initially Druckenmiller put several million into a bet that the mark would rally, but later, on Soros's say-so, he increased his purchase to about $2 billion. The mark rallied, and Druckenmiller made the fund $1 billion. [2]

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John Arnold - Bet On Rival Failing and Won!

John Douglas Arnold (born 1974) is an American billionaire, philanthropist, former hedge fund manager, and former natural gas trader. His firm, Centaurus Advisors, LLC, was a Houston-based hedge fund specializing in trading energy products that closed in 2012. Arnold became the youngest billionaire in the U.S. in 2007. He now focuses on philanthropy through Arnold Ventures LLC.

During the collapse of Amaranth Advisors, Centaurus is widely credited as being one of the major players on the other side of their position, returning as much as 150% in 2005. [1]

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James Chanos - $500 Million Betting Enron Would Fail

James S. Chanos (born December 24, 1957) is an American investment manager. He is president and founder of Kynikos Associates, a New York City registered investment advisor focused on short selling. A noted art collector, he appeared on the BBC Four documentary The Banker's Guide to Art.

Chanos was a short seller of Enron throughout 2001, increasing his short position as more information surfaced. Kynikos profited from the trade. He gained notability as a short seller when he predicted the fall of Enron Corp. before it filed for bankruptcy in 2001. [1]

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Andy Krieger - Shorted New Zealand Dollar for $300 Million

In 1987, Andy Krieger, a 32-year-old currency trader at Bankers Trust, was carefully watching the currencies that were rallying against the dollar following the Black Monday crash. As investors and companies rushed out of the American dollar and into other currencies that had suffered less damage in the market crash, there were bound to be some currencies that would become fundamentally overvalued, creating a good opportunity for arbitrage. The currency Krieger targeted was the New Zealand dollar, also known as the kiwi.

Using the relatively new techniques afforded by options, Krieger took up a short position against the kiwi worth hundreds of millions of dollars. In fact, his sell orders were said to exceed the entire money supply of New Zealand. The selling pressure combined with the lack of currency in circulation caused the kiwi to drop sharply. It yo-yoed between a 3 and 5% loss while Krieger made millions for his employers. [1]

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John Paulson - Achieved a $4 Billion Win Betting Against Subprime Mortgages

John Alfred Paulson (born December 14, 1955) is an American billionaire hedge fund manager. He leads Paulson & Co., a New York-based investment management firm he founded in 1994. He has been called "one of the most prominent names in high finance" and "a man who made one of the biggest fortunes in Wall Street history."

His prominence and fortune were made in 2007 when he earned almost $4 billion and was transformed "from an obscure money manager into a financial legend" by using credit default swaps to effectively bet against the U.S. subprime mortgage lending market. In 2010, Paulson earned $4.9 billion. The Forbes real-time tracker estimated his net worth at $4.2 billion as of May 2020. [1]

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Rob Lay
Rob Lay is the Founder and Editor-in-Chief at ManLife.com, Founder of FerrariChat.com, and Owner at Lay Properties, LLC. Rob has a B.S. from Babson College and M.B.A. from University of Dallas along with executive training from SMU. Rob has enjoyed various activities from competitive swimming in college, running several marathons, competed at triathlon nationals, competed at national club car racing, 1,000+ hour private instrument pilot, competed as a co-angler national FLW bass tour, and big game hunting around North America. Rob wants to share his experiences and learn from other middle-aged men in the ManLife Community. You can also find Rob on Instagram and LinkedIn.

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