The Greatest
Trades Ever Made

Breaking the Bank of England

$1 billion

Soros recognized the British pound was overvalued within the European Exchange Rate Mechanism and that the Bank of England couldn't sustain the peg against the Deutsche Mark.

Buying Coca-Cola

$25 billion+

Buffett recognized Coca-Cola as the world's strongest brand with unmatched pricing power, bought after the 1987 crash when the stock was temporarily depressed.

The Greatest Trade Ever

$15 billion

Paulson identified that subprime mortgage-backed securities were drastically mispriced and used credit default swaps to bet against them before the housing market collapsed.

Calling the 1929 Crash

$100 million

Livermore read the tape and market psychology perfectly, recognizing the speculative mania of the late 1920s was unsustainable and positioned short before the historic crash.

Buying 104 Stocks Under $1 During WWII

400% average return

When Nazi Germany invaded Poland and panic gripped markets, Templeton borrowed $10,000 and bought every stock trading under $1 on the NYSE, betting that fear creates the best bargains.

Predicting Black Monday

62% monthly return

Tudor Jones studied the 1929 crash pattern, recognized eerie parallels in 1987's market structure, and positioned heavily short before the largest single-day crash in US history.

Medallion Fund

66% average annual return

Simons, a world-class mathematician and codebreaker, proved that statistical pattern recognition could consistently extract returns from financial markets at a scale no human trader could match.

Fidelity Magellan Fund

29.2% annual return over 13 years

Lynch proved that an ordinary person paying attention to everyday life could identify winning investments before Wall Street, growing Magellan from $18 million to $14 billion.

Subprime Mortgage Short

$700 million for the fund, $100 million personal

Burry, a physician-turned-hedge-fund-manager, analyzed individual mortgage loans and discovered that the housing market was a house of cards built on fraud and unsustainable lending.

Buying GEICO

$50 billion+ (as part of Berkshire)

When GEICO was near bankruptcy and its stock had fallen 95%, Buffett recognized the company's low-cost direct insurance model was still fundamentally sound and began aggressively buying.

All-In on Bank Stocks

$7 billion for Appaloosa

In March 2009 at peak financial panic, Tepper bet that the US government would not let major banks fail and loaded up on beaten-down bank stocks at generational lows.

First Outside Investment in Facebook

$1 billion+

Thiel saw Facebook as more than a college social network — he recognized it as a potential monopoly platform that could capture the social graph of the entire world.

Investing in Alibaba

$60 billion+

Son bet that Jack Ma and Alibaba would become the Amazon of China, investing $20 million after a six-minute meeting during the depths of the dot-com bust.

German Reunification Trade

$2 billion+

When the Berlin Wall fell, Druckenmiller immediately recognized that German reunification would require massive fiscal spending, strengthening the Deutsche Mark enormously.

Apple Activist Investment

$2 billion+

Icahn recognized that Apple was deeply undervalued relative to its cash generation and advocated for massive share buybacks to unlock value for shareholders.

COVID-19 Credit Hedge

$2.6 billion from $27 million

Ackman saw COVID-19 spreading globally and realized credit markets were not pricing in the economic devastation a pandemic would cause, buying cheap credit protection.

Bank of America Preferred + Warrants

$30 billion+

During the European debt crisis when banks were being sold off again, Buffett invested $5 billion in Bank of America preferred stock with warrants, betting on America's largest bank at distressed prices.

American Express During the Salad Oil Scandal

500%+ return

When a fraud scandal caused American Express stock to crash 50%, a young Buffett recognized the core charge card business was completely unaffected and bet big.

Acquiring See's Candies

$2 billion+ in cumulative pre-tax earnings

Buffett paid $25 million for a candy company with strong brand loyalty and pricing power, which taught him that great brands justify premium prices — transforming his entire investing philosophy.

Goldman Sachs Preferred Shares

$5 billion+

In the depths of the 2008 financial crisis, Buffett invested $5 billion in Goldman Sachs preferred stock with a 10% dividend and lucrative warrants, betting that Goldman and the financial system would survive.

Bridgewater's 2008 Performance

9.5% return (vs -37% S&P 500)

Dalio's deep study of debt cycles and deleveraging led him to position Bridgewater's Pure Alpha fund defensively before and during the 2008 crisis, generating positive returns while the world burned.

Distressed Debt During the Financial Crisis

27% in 2009

Klarman's Baupost Group, known for extreme patience and holding cash for years, deployed billions into distressed debt at the depths of the crisis, buying assets for pennies on the dollar.

Vanguard Windsor Fund

13.7% annual vs 10.6% S&P 500 over 31 years

Neff demonstrated that buying unfashionable, low P/E stocks with sound fundamentals — what he called 'ugly ducklings' — could consistently beat the market over three decades.

Motorola

Held until death — multi-thousand-percent return

Fisher pioneered growth investing by buying Motorola when it was primarily a car radio company, seeing that its R&D culture would lead it to dominate multiple technology waves over decades.

Original GEICO Investment

Multi-hundred-percent return, transformed his portfolio

Graham, the father of value investing, recognized that GEICO's direct-to-consumer insurance model gave it a permanent cost advantage over traditional agent-based insurers.

Tiger Management's Legendary Run

31.7% annual return over 20 years

Robertson combined deep fundamental research with macro conviction, building Tiger into the most successful hedge fund of its era and spawning a dynasty of 'Tiger Cub' managers.

Soybean Futures

Turned $3,000 into $23,000, launching his career

Kovner, a cab driver and Harvard dropout, used $3,000 borrowed against his credit card to make his first futures trade on soybeans, launching one of the most successful macro trading careers in history.

Kuwait Invasion Oil Trade

86% annual return

Bacon read the geopolitical signals of Saddam Hussein massing troops on the Kuwait border and went long oil futures before the invasion, capturing the ensuing price spike.

Broadcast.com Sale + Collar Hedge

$2 billion+ (protected via collar)

Cuban sold Broadcast.com to Yahoo at the peak of the dot-com bubble for $5.7 billion, then brilliantly hedged his Yahoo stock with a collar to lock in the gains.

15 Consecutive Years Beating the S&P 500

15 consecutive years of outperformance

Miller combined deep value investing with an openness to technology stocks that traditional value investors avoided, creating the longest market-beating streak in mutual fund history.

Princeton Newport Partners

19.8% annual net return with minimal volatility

Thorp, a mathematics professor who first beat blackjack, applied quantitative methods to financial markets decades before 'quant' became a buzzword, pioneering convertible bond arbitrage and warranted hedging.

Tesla Long Position

$6 billion+

Baron invested in Tesla when most Wall Street analysts dismissed it, holding through extreme volatility because he believed Elon Musk would revolutionize both the auto industry and energy storage.

Blackstone Acquires Hilton Hotels

$14 billion

Blackstone bought Hilton Hotels for $26 billion at what seemed like the worst possible timing — right before the financial crisis — but their operational improvements and patience turned it into the most profitable private equity deal in history.

RJR Nabisco Leveraged Buyout

Modest financial return, but transformed the industry

KKR's $25 billion buyout of RJR Nabisco was the deal that defined the leveraged buyout era, proving that financial engineering and operational improvement could unlock value in America's largest corporations.

Selling Equity Office Properties at the Top

$39 billion exit

Zell, the 'Grave Dancer' of real estate, sold his massive office REIT at the peak of the commercial real estate bubble in February 2007 — months before the crash.

Titan Industries

~$1.5 billion from initial investment of ~$10 million

India's Warren Buffett recognized that Titan — a Tata Group company making watches and jewelry — would benefit enormously from India's rising middle class and the shift from unorganized to organized retail.

Buying Hong Kong Real Estate During Riots

Built a $30 billion+ fortune

When communist-inspired riots sent Hong Kong into panic and property values crashed, Li Ka-Shing bought everything he could, betting that Hong Kong's fundamental advantages would endure.

Wesco Financial & See's Candies Philosophy

Multi-billion-dollar compounding

Munger convinced Buffett to pay up for quality businesses with durable competitive advantages, fundamentally transforming Berkshire Hathaway's investing philosophy from cheap cigar butts to wonderful companies at fair prices.

Citadel Founding Trades

Built a $60 billion+ AUM empire

Griffin started trading convertible bonds from his Harvard dorm room, installing a satellite dish on the roof to get real-time quotes, and turned that edge into one of the most successful hedge funds in history.

GameStop Deep Value Thesis

$50,000 → $48 million+

Gill identified GameStop as a deep value play trading below liquidation value, with potential catalysts from new console cycles and e-commerce pivot, and shared his thesis transparently online.

Uber & Twitter Angel Investments

$5 billion+

Sacca, through his Lowercase Capital fund, made early-stage bets on Twitter and Uber by recognizing the power of mobile platforms and the network effects of marketplace businesses.

a16z Portfolio: Coinbase, GitHub, Airbnb

Multi-billion-dollar returns

Andreessen, who created the first web browser, founded a16z on the thesis that 'software is eating the world' and built a new model for venture capital that combined investing with operational support.

Oaktree Distressed Debt During GFC

Multiple billions across distressed funds

Marks deployed Oaktree's largest-ever distressed debt fund at the depths of the financial crisis, buying high-quality bonds at 50-60 cents on the dollar when forced selling created extraordinary bargains.

Pioneering Growth Investing

Built a $1.5 trillion+ asset management firm

Price invented the concept of 'growth stock investing' — buying companies with above-average earnings growth potential and holding them for the long term, a radical departure from the dividend-focused investing of his era.

US Steel Industry Consolidation

$4.5 billion

Ross bought bankrupt US steel companies for pennies on the dollar, consolidated them into the International Steel Group, then sold to Mittal Steel for a massive premium.

Contrarian Trading in the 1970s

24.5% annual net return over 28 years

Steinhardt generated 24.5% annual returns for 28 years by combining aggressive contrarian stock picking with prescient macro calls, including bold bets on bonds during the Volcker era.

Creating the Index Fund

Saved investors trillions in fees

Bogle proved that most active managers fail to beat the market after fees, and created the first index fund available to individual investors — the greatest innovation in investment history for ordinary people.

Acquiring Burlington Northern Santa Fe

$100 billion+ in value creation

Buffett called it 'an all-in wager on the economic future of the United States,' buying America's largest railroad at the depth of the Great Recession.

NVIDIA's AI and Data Center Pivot

$3 trillion+ market cap creation

Huang bet that GPU computing would become the foundation of artificial intelligence, pivoting NVIDIA from a gaming graphics company into the most important computing company of the AI era.

Netflix: DVD to Streaming Pivot

$300 billion+ market cap creation

Hastings cannibalized Netflix's profitable DVD-by-mail business to pivot to streaming, enduring a 75% stock crash and massive subscriber losses, but ultimately creating the dominant entertainment platform of the 21st century.

Netflix — 10x in Two Years

$2 billion+

After Netflix's Qwikster debacle crashed the stock 75%, Icahn recognized the streaming business was still growing rapidly and bought heavily at the bottom.

Yahoo Activist Campaign

$1 billion+

Loeb recognized that Yahoo's Alibaba stake alone was worth more than Yahoo's entire market cap, waged a successful activist campaign to install new management, and unlocked the hidden value.

DuPont Activist Campaign

Multi-billion-dollar value creation

Peltz pushed DuPont to separate its diverse businesses, arguing that each unit would be more valuable as a standalone entity — a thesis ultimately vindicated by the DowDuPont merger and three-way split.

Apollo's Caesars Entertainment Deal

Multi-billion-dollar returns across Apollo portfolio

Apollo Global Management acquired Caesars Entertainment and navigated one of the most complex restructurings in history, ultimately preserving and growing value through operational improvements and real estate monetization.

Beal Bank Distressed Debt Buying

Estimated $7 billion+ in personal wealth creation

Beal, a self-taught banker and poker player, deliberately shrank his bank's assets before the crisis, then aggressively bought distressed loans and assets when others were forced to sell.

Argentine Government Bond Holdout

2,400% return

Singer's Elliott Management bought defaulted Argentine government bonds at steep discounts and refused to accept the country's restructuring terms, fighting for full payment in courts for 15 years — and winning.

Asian Financial Crisis Currency Trades

$750 million+

Soros identified that several Asian currencies were overvalued and pegged at unsustainable levels, applying the same framework he used against the British pound five years earlier.

Natural Gas Trading

$4 billion+ personal fortune by age 38

Arnold, a former Enron trader, understood natural gas fundamentals — supply, demand, weather, storage — better than anyone on Wall Street, generating billions through his Centaurus Energy fund.

Union Pacific Railroad Turnaround

$5 billion+

Anschutz acquired a large stake in Southern Pacific Railroad, pushed for its merger with Union Pacific, and rode the consolidation of American railroads to enormous profits.

Disney Investment

$1 billion+

The Bass brothers recognized that Disney was deeply undervalued — its film library, theme parks, and real estate were worth far more than the stock price — and helped install new leadership to unlock the value.

JPMorgan's Bear Stearns & WaMu Acquisitions

$50 billion+ in value creation

Dimon seized the opportunity of the financial crisis to acquire Bear Stearns and Washington Mutual at distressed prices, dramatically expanding JPMorgan's franchise at a fraction of replacement cost.

Tesla Conviction Buy

500%+ return on position

Wood was one of the first institutional investors to publish a bull case for Tesla with a $4,000 price target (pre-split), arguing that autonomous driving and energy storage would make Tesla worth far more than traditional automakers.

Walmart: From One Store to Empire

$150 billion+ family fortune

Walton bet that discount retail could work in small-town America, where competitors refused to go, and built the world's largest company by relentlessly cutting costs and passing savings to customers.

Nike: From $50 to a $200 Billion Empire

$40 billion+ personal fortune

Knight recognized that high-quality running shoes could be imported from Japan at a fraction of the cost of German competitors, and built a global brand around athletic aspiration.

Founding Amazon

$200 billion+ personal fortune

Bezos left a lucrative Wall Street job because he calculated that the internet was growing at 2,300% per year and books were the perfect product to sell online due to their catalog size and uniformity.

Apple's Comeback

$3 trillion+ market cap creation

Jobs returned to a nearly bankrupt Apple and bet the company's future on beautifully designed consumer products — the iMac, iPod, iPhone, and iPad — creating the most valuable company in history.

Tiger Global's Tech Investing

$45 billion+ in net gains for investors

Coleman, a Julian Robertson protege, built Tiger Global into the dominant tech-focused hedge fund by combining deep fundamental research with aggressive positioning in high-growth internet companies worldwide.

Viking Global Investors

$45 billion+ in net gains

Another Tiger cub, Halvorsen built Viking into one of the most consistently profitable hedge funds by combining exhaustive fundamental research with disciplined risk management.

Going Long Gold

$5 billion+

After his legendary subprime short, Paulson pivoted to gold, arguing that massive government stimulus and money printing following the financial crisis would inevitably lead to inflation and currency debasement.

D.E. Shaw Quantitative Strategies

Built $60 billion+ AUM

Shaw, a Columbia computer science professor, founded one of the first truly quantitative hedge funds, proving that computational approaches to markets could generate consistent alpha at scale.

Kleiner Perkins: Google & Amazon

$10 billion+

Doerr, the legendary Kleiner Perkins partner, backed both Amazon and Google in their earliest stages, recognizing that the internet would create the most valuable companies in history.

Sequoia's Cisco Investment

$2 billion+

Valentine, the founder of Sequoia Capital, backed Cisco Systems when it was building networking equipment in a Stanford couple's living room, betting that computer networking would become essential infrastructure.

eBay Investment

$5 billion+

Benchmark partner Bob Kagle invested $6.7 million in eBay for 22% of the company, recognizing that online auctions created a perfect marketplace with powerful network effects.

Taking Dell Private and Back Public

$50 billion+ in value creation

Dell took his struggling PC company private to transform it away from Wall Street's quarterly earnings pressure, pivoted to enterprise infrastructure, then took it public again at a dramatically higher valuation.

Spanx: From $5,000 to a Billion-Dollar Brand

Became youngest self-made female billionaire

Blakely identified a gap in women's undergarments that no major company had addressed, invested $5,000 of her savings, and built Spanx into a billion-dollar brand without taking a single dollar of outside investment.

Starbucks: From 6 Stores to 35,000

$100 billion+ market cap creation

Schultz bought Starbucks' 6 stores for $3.8 million after visiting Italy and realizing Americans would embrace European coffee culture — creating an entirely new consumer category.

Democratizing Investing

$100 billion+ market cap creation

Schwab bet that deregulation of brokerage commissions would allow him to undercut traditional brokers, making investing accessible to everyday Americans for the first time.

Pioneering Emerging Markets Investing

Built $50 billion+ in EM assets under management

Mobius traveled to countries most investors feared — Turkey, Nigeria, Vietnam, frontier markets — finding undervalued companies decades before emerging markets became mainstream.

Co-founding the Quantum Fund with Soros

4,200% return in 7 years (vs 47% S&P 500)

Rogers provided the deep research and fundamental analysis that underpinned Soros's trading, together producing one of the greatest fund performances in history during the 1970s.

MGM & Chrysler — Buy, Fix, Repeat

$10 billion+ cumulative

Kerkorian, a self-made billionaire who dropped out of school in 8th grade, made his fortune by repeatedly buying undervalued companies, improving them, and selling at a profit — most famously MGM and Chrysler.

Sprint-T-Mobile Merger Bet

$40 billion+ in value realization

Son acquired Sprint and spent seven years pushing for a merger with T-Mobile, enduring regulatory rejection and billions in losses before the merger finally closed and created a telecom powerhouse.

Chipotle Turnaround

$1.5 billion+

After E. coli outbreaks devastated Chipotle's stock, Ackman recognized the brand's enduring strength, invested $1.2 billion, helped install a new CEO, and rode the turnaround.

Oracle's Cloud and AI Pivot

$200 billion+ in market cap growth

Ellison bet Oracle's future on cloud infrastructure and AI, spending billions to build data centers while skeptics said Oracle was too late — then rode the AI wave to dramatic stock appreciation.

Fidelity's Crypto and Digital Assets Expansion

Strategic positioning worth billions

Johnson made Fidelity one of the first major financial institutions to embrace cryptocurrency, launching Fidelity Digital Assets in 2018 — years before competitors — positioning the firm for the digital asset revolution.

GAMCO Private Market Value Investing

Managed $30 billion+ at peak

Gabelli pioneered 'Private Market Value with a Catalyst' investing — estimating what a private buyer would pay for a public company and investing when the stock traded at a significant discount.

Building a Media Empire Through Ownership

$2.5 billion+ net worth

Winfrey made the pivotal business decision to own her show rather than just star in it, creating Harpo Productions and retaining ownership of content — a decision that turned talent into a business empire.

Early Intel & Apple Investments

Multi-billion-dollar returns across portfolio

Rock, considered the father of venture capital, backed Intel's founding and Apple's early rounds, proving that betting on extraordinary founders building transformative technology is the highest-return strategy in investing.

Investing in Career Longevity via TB12 Method

$500 million+ in career earnings and business value

Brady's greatest 'trade' was investing in his own body and longevity, playing at the highest level until age 45 and turning his method into a brand — the ultimate long-term compounding strategy.

Building the World's Biggest Podcast

$250 million+ Spotify deal + ongoing value

Rogan built the world's most popular podcast by having genuine long-form conversations with fascinating people — then monetized it through the largest podcast deal in history.

VaynerMedia & Early Angel Investments

$200 million+ net worth from media + angel portfolio

Vaynerchuk built a $250M+ digital agency and made early angel investments in companies like Facebook, Twitter, Uber, and Snapchat — all while documenting his journey and building a massive personal brand.

Gym Launch to Acquisition.com Portfolio

$100 million+ portfolio value

Hormozi built, scaled, and sold gym turnaround businesses, then used the playbook to build Acquisition.com — investing in small businesses and applying proven growth frameworks to scale them.

Silicon Valley Angel Portfolio

Multi-hundred-million-dollar portfolio

Ferriss leveraged his platform as a bestselling author and podcast host to gain access to top-tier startup deals, building one of the most successful individual angel portfolios in Silicon Valley.

PHP Agency & Valuetainment

Built $100 million+ in combined business value

Bet-David, an Iranian immigrant who arrived in the US as a refugee, built PHP Agency into one of the fastest-growing financial services marketing firms while simultaneously building Valuetainment into a top business media brand.

Omega Advisors Value Investing

13%+ annual returns over 27 years

Cooperman, a former Goldman Sachs research chief, built Omega Advisors into one of the most respected value-oriented hedge funds, known for deep fundamental research and concentrated positions in undervalued companies.

Vista Equity Partners

Built $100 billion+ AUM, 22% net IRR

Smith focused exclusively on enterprise software companies, applying rigorous operational playbooks to improve margins and growth at acquired companies — generating one of the best track records in private equity history.

DoubleLine Launch & Bond Market Calls

Built $90 billion+ AUM

Gundlach, the 'Bond King,' launched DoubleLine after leaving TCW and built it into one of the largest fixed income managers by making consistently prescient calls on interest rates and the economy.

Turning Intellectual Capital into a Global Brand

$50 million+ in book sales, speaking, and media

Peterson transformed academic psychology lectures into a global self-improvement brand, proving that deep intellectual content can reach massive audiences when combined with modern media platforms.

Huberman Lab — Science Communication Empire

$50 million+ in brand and business value

Huberman transformed his Stanford neuroscience expertise into the world's most popular science podcast, proving that rigorous academic content can achieve massive mainstream appeal.

Can't Hurt Me — Monetizing Mental Toughness

$30 million+ in book and brand value

Goggins, a former Navy SEAL and ultramarathon runner, self-published 'Can't Hurt Me' and built a massive brand around mental toughness and self-discipline, proving that an authentic personal story can create outsized value.

Building Berkshire Hathaway Over 60 Years

4,384,748% total return (1965-2024)

The greatest trade of all time isn't a single trade — it's Buffett's 60-year compounding machine at Berkshire Hathaway, turning a failing textile company into the most successful conglomerate in history through patient capital allocation.