Good morning, traders…
I’ll never forget the first time I saw “The Last Shot.”
It was Game 6 of the 1998 NBA Finals. Chicago Bulls vs. Utah Jazz.
It was also the last professional game of Michael Jordan’s career.
Everyone knew what was at stake: Jordan’s legacy, the Bulls’ dynasty, maybe even the end of an era…
The game was a slugfest in Salt Lake City. The crowd was deafening. The tension was palpable. Every possession felt like it could tilt history forever.
With less than a minute left, the Bulls trailed 86–83.
Then Jordan made his move.
He drove straight to the rim for a quick layup and drained it.
86–85.
On the next play, he stripped the ball clean from Karl Malone in the post, like a thief in the night. No timeout. No hesitation.
He brought the ball up himself, calm as ever.
Then came the moment.
Guarded by Bryon Russell at the top of the key, Jordan dribbled right, crossed back left, and pulled up. The perfect form, the perfect release.
Time seemed to freeze. The ball arced through the air. When it dropped, the entire arena fell silent. Jordan hitting that iconic follow-through, arm extended, holding the pose as if he knew he’d just closed the book on basketball immortality…
87–86, Chicago.
That jumper sealed his sixth championship and capped the perfect ending to the Jordan era.
Jordan had been preparing for that moment his entire career. The fundamentals. The footwork. The thousands of hours in the gym. The pressure situations he’d faced before.
When the moment came, he didn’t hesitate. He shot his shot.
At that moment, I knew I wanted to play basketball.
Several years and thousands of hours of practice later, I was playing Division I for the University of New Hampshire.
But I never would’ve reached those heights without that initial spark of inspiration from the great Michael Jordan.
These days, I’m inspired by legendary trading moments…
Trades that changed markets. Moves that turned thousands into millions (or millions into billions).
Traders who saw something nobody else saw and had the conviction to act on it.
I want to tell you the stories behind five of the greatest trades of all time.
Who knows, one of these trades just might inspire you to become the trader you dream of being…
Just like Michael Jordan did for me.
1992: George Soros and Stanley Druckenmiller “Break the Bank of England”
In 1992, George Soros and a young Stanley Druckenmiller made one of the most audacious bets in financial history.
They believed the British pound was overvalued and the government couldn’t maintain its peg.
But they didn’t just sell the pound. They shorted it aggressively.
In a genius move, they used put options to amplify the position.
When the British government finally gave up trying to support the currency, the pound collapsed. That day is now known as Black Wednesday.
Soros walked away with an estimated $1 billion. The trade showed the world what happens when deep macroeconomic analysis meets the conviction to act on it.
The Lesson: Going against the crowd can pay dividends if you’ve done your homework. Soros and Druckenmiller understood the fundamentals better than the government defending the currency. When you have a strong thesis backed by research, believe in your conviction. Options give you the leverage to amplify that conviction (especially in bearish environments).
2008: Nassim Nicholas Taleb’s ‘Black Swan’ Trades
The Trade: Best-selling author and options trader Nassim Nicholas Taleb has written some incredible books on risk management and derivatives strategy.
Better yet, he puts his money where his mouth is…
Taleb has a unique strategy. He doesn’t go long.
Instead, he buys extremely far out-of-the-money index puts, VIX calls, and bearish debit spreads.
Most days, his account loses a small amount. He doesn’t care.
Eventually, a day comes when volatility explodes, stocks tank, and spreads blow out.
On these days, Taleb makes a fortune. An amount so large it makes up for every day of small losses … and then some.
This strategy paid off handsomely during the Great Financial Crisis…
While most funds were registering severe losses in 2008, Universa reported gains of over 100%.
Even more incredibly, Taleb did it again just a few years later…
In the late summer of 2015, Taleb was doing his usual thing, buying cheap SPY puts and VIX calls.
Then, on August 24, the S&P 500 dropped 8% intraday while the VIX surged 50%.
As the rest of the market was panic-selling, Taleb’s entire portfolio increased by 20%. He reportedly profited more than $1 billion in a single day.
The Lesson: Always be prepared for anything in the stock market. Taleb dubbed these events “black swans” for a reason: They’re rare. We can’t see them coming. This is why I watch market internals so closely. It’s why I hedge when they start flashing red signals. If you know how to use options to protect your longs, you can actually make huge gains in a crash … while everyone else is getting destroyed.
2015: Mystery Trader Turns $110k into $2.3 Million in 28 Minutes
In March 2015, someone turned $110,000 into $2.4 million in 28 minutes.
Intel Corporation (NASDAQ: INTC) announced it was in advanced talks to acquire Altera. The news broke. And within moments, this trader bought 3,158 out-of-the-money call options on Altera for $0.35 per contract.
The options exploded to $7.60 each. A 2,071% gain in less than half an hour.
Was it a human watching the news feed? Was it an algorithm scanning headlines and executing instantly? Nobody knows.
What we do know is that someone saw the opportunity, understood what it meant, and acted before the rest of the market caught up.
The Lesson: Speed matters. When breaking news hits, seconds count. Whether it’s you watching a live feed or an algorithm scanning for keywords, having the infrastructure to act quickly on market-moving information can turn minutes into millions. This style of day trading isn’t for everyone. But when done effectively, it can be deadly.
2020: Bill Ackman’s $2.3 Billion COVID-19 Hedge
In 2020, Bill Ackman saw what was coming before the market did.
His firm, Pershing Square Capital Management, spent $27 million on credit protection, buying insurance against a market collapse.
Then he went on CNBC and said, “Hell is coming,” adding that Hilton and “every other hotel company was going to zero.”
The market didn’t like hearing that. Shocker.
But Ackman’s portfolio loved it.
When markets tanked in March 2020, his $27 million hedge turned into $2.6 billion. Nearly 10x.
He then flipped bullish near the bottom and started aggressively buying stocks.
Was the CNBC appearance controversial? Absolutely. Was he right to hedge his portfolio when COVID became a reality? Without question.
The Lesson: This trade shows the value of flexibility. Ackman didn’t stay bearish. He flipped bullish after the crash and bought beaten-down stocks. How much do you think he’s up on those positions today? Be nimble and adapt to what the market gives you.
What These Trades Can Teach You
These five trades span multiple decades, continents, and market environments.
Soros and Druckenmiller went against the crowd with deep macro analysis. Taleb had a unique strategy and executed with precision. The mystery trader reacted to breaking news faster than the market. And Ackman hedged his portfolio before disaster struck.
But they all share the same core principles: conviction, timing, and understanding how to use options to amplify potential gains.
You don’t need a $10 billion portfolio to apply these lessons.
You need a process, discipline, and the fortitude to act quickly when opportunities arise.
So, tell me…
Will you keep playing guessing games in the options market?
Or will you start weaponizing the 1 strategy that works in 80% of market conditions?*
I’m talking about the same approach I used to turn $50 into $1,260 in just 2 months while stocks struggled with trade war uncertainty.*
This single strategy recently delivered my team 64 winning trades in a row.*
I’m about to reveal exactly how to use this strategy to your advantage during my Simpler Options 2-Day Virtual Bootcamp.
I’ll show you:
- The only strategy you should focus on right now. The same approach that helped my students catch 123 doubles in the past 12 months.*
- The 3 simple rules that keep you out of trouble. The guidelines that helped one student go from $600 to $3,000 in his third week.*
- My personal checklist for every trade. The systematic process that removes guesswork and emotional decisions.
- Why this approach feels just like trading stocks (but with significantly more leverage and precision).
If you’ve been wanting to understand how options really work, now is the time…
The market won’t wait for you to figure this out on your own.
Join Me at the SIMPLER OPTIONS 2-Day Virtual Bootcamp on October 28-29 @ 12 p.m. ET/9 a.m. PT
Happy trading,
Ben Sturgill
*Past performance does not indicate future results. Not typical.