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Hello,

I had a long walk-and-talk with one of my hedge fund friends from London.

We discussed some of the top investment bets in history.

From time to time, an investor sees what others don’t and stakes everything on it.

These are not usual trades.

They’re audacious bets remembered in financial history, delivering jaw-dropping outcomes.

Big bets have the same things in common - huge conviction + specific timing + high risk.

Buckle up.

Here are 10 of the most iconic calls ever made:

1) George Soros – Shorting the British Pound in 1992

In 1992, Soros wagered against the pound, betting the UK would exit the European Exchange Rate Mechanism (ERM) - and he won.

His Quantum Fund reportedly pocketed around £1 billion.

2) John Paulson – Betting Against Subprime Mortgages in 2007

In 2007, Paulson & Co. bought credit default swaps (CDS) protection on mortgage-backed securities.

The bet paid off - his fund earned around $15 billion, with Paulson personally pocketing about $4 billion once the crisis hit.

3) Michael Burry – Early Subprime Shorts in 2005–2008

Burry began loading up on CDS in the mid-2000s (you might know this from The Big Short).

The payoff came in 2007–08, bringing huge returns and reportedly landing him around $100 million personally.

4) Paul Tudor Jones – Predicting Black Monday in 1987

Jones correctly anticipated the 1987 crash, shorted the market, and reportedly earned about $100 million as portfolios returned roughly 200% net.

5) Bill Ackman – The COVID Hedge in 2020

As the pandemic started roiling markets, Ackman’s Pershing Square spent $27 million on credit protection.

When markets crashed in March, those hedges ballooned to $2.6 billion in less than a month - one of the most profitable short-term trades in history.

6) Louis Bacon – Oil Play during the Gulf War in 1990

Bacon went long oil and short stocks, anticipating the geopolitical fallout from the Iraq crisis.

His fund returned 86% that year.

7) Andrew Hall – Betting Oil Would Hit $100 in 2003–2008

In 2003, with oil at around $30/barrel, Hall bet it would climb to $100 within five years.

It did, and he earned $100 million through Citigroup’s structured deal.

8) David Tepper – Big Bank Rebound in 2009

In the wake of the financial crisis, Tepper scooped up beaten-down bank stocks.

By year’s end, Citigroup tripled and Bank of America quadrupled.

Tepper’s fund netted $7 billion with himself earning around $2 billion.

9) Jim Chanos – Shorting Enron in 2000–2001

Chanos went public with short positions against Enron by late 2000.

When the company collapsed in December 2001, his firm reportedly made hundreds of millions.

10) Mark Cuban – Selling Broadcast.com at the Peak in 1999

Cuban co-founded Broadcast.com, an early streaming company, and sold it to Yahoo in 1999 for $5.7 billion in stock - right before the dot-com bubble burst.

He wisely hedged his Yahoo shares locking in the value.

When the tech market collapsed, Cuban walked away as one of the few internet-era billionaires who kept nearly all of his fortune.

What do these trades teach us?

Profound conviction, perfect timing, and contrarian thinking can produce life-altering outcomes.

Some trades were grounded in macro foresight, some in deep fundamental insight, and some in sheer boldness.

This is where strategy meets nerve.

That said, these trades are definitely not for everyone - many other bets have resulted in losses, as you can never 100% predict the outcomes.

Long-term diversified investing remains the more reliable way to build wealth.

However, some choose to have “satellite” trades on top of their core holdings when they spot rare opportunities.

Just remember: never risk more than you can afford to lose.

This is not a game - this is life.

By the way, on Wednesday, September 24, at 8 AM ET, I’m sharing something special designed for you:

The smarter way to build long-term wealth, spot great opportunities, and invest with confidence - without turning investing into a full-time job.

But it will only be available to a very small group of people.

It’s something I’ve never done before, and probably never will do again.

Be ready on Wednesday, September 24, at 8 AM ET.

To more wins!
Igor