How I'm Trading The Most Dangerous Time Of The Year For Stocks

Last week, I showed you why August and September are historically the most dangerous months for investors.

The data is clear: this is the season when stocks stumble and traders who aren’t prepared take the hit.

My Money Calendar utilizes 10 years of market data to provide a clear picture of the market’s overall trend.

And as I showed you last time, it’s literally flashing yellow right now. 

Now, for plenty of traders, this is enough to move to cash and hit the sidelines, wait for the dust to settle and for markets to rebound in October and November. 

That’s a big mistake because a falling market can be just as profitable as a rising one.

The 6X Strategy To Trade This Fall’s Seasonal Patterns

History shows that August through October are the toughest months for stocks. Tom Gentile’s seasonal trading system flips that weakness into opportunity, already delivering a 58% return in 2025—six times the S&P 500. Past performance doesn’t guarantee future results. You’re invited to join him live this Wednesday at 6 PM ET to see the exact bullish and bearish trades he’s preparing now.

Two Ways To Trade Seasonal Bearishness

Markets have an upward bias over time, and more often than not, I’m tracking stocks that have gone UP at least nine of the last 10 years – giving them a 90% or better probability of making a profitable move to the upside. 

When the Calendar looks like this, as it did back in May, it’s easy to profit from the overall bullish trend:

Remember, green days indicate more bullish patterns among the stocks that Money Calendar tracks, setting the stage for an overall bullish month.

So what do we do when the calendar flips to yellow – and we head into bearish territory, as we’re doing today? 

Unlike most traders, I don’t change my entire strategy.  

The Money Calendar also tracks stocks that have gone DOWN at least nine of the last 10 years – giving them a 90% or better probability of making a profitable move to the downside. 

When the Money Calendar is forecasting seasonal bearishness, as it is now, I have two tactics to consider:

1. Trade The Downside Directly

The Money Calendar doesn’t just spot bullish rallies. It also identifies stocks that consistently fall during specific windows of the year. 

When that happens, we don’t sit on the sidelines. We use:

• Puts to profit from the drop directly. And just like with the call trades I recommend,
• Put spreads to reduce cost and risk while still targeting 100% gains in as few as 30 days.

Apart from the direction, however, nothing else about my strategy changes. I still only trade patterns that have a 90% or better probability for profit. I still create trades using options that can deliver 100% gains or more in about 30 days. 

Instead of fearing the selloff, we flip it into a payday. But we don’t simply flip the switch and only trade puts because there’s a special group of stocks that I like to keep an eye on.

2. Find the Bullish Outliers

Here’s the beauty of pattern recognition: even in bearish markets, some stocks buck the trend.

The Money Calendar highlights these rare outliers — stocks that have gone UP at least nine of the last 10 years during August and September.

And because they’ve proven themselves against the broader trend over the last 10 years, we can still take a strong bullish pattern when the trend is overall bearish. 

That means we can still deploy calls or call spreads to take advantage of their strength, even while the broader market struggles.

I Know Exactly What I’m Trading In August And September

Thanks to the Money Calendar, which gives me the start and end date of these profitable patterns, I don’t need to panic, I don’t need to sell, and I don’t need to change my strategy. 

In fact, I already know what I’m trading this month AND next. 

That’s why I’m inviting you to join me for a free live event on Wednesday, August 27, at 6 PM ET. I’ll show you how to turn this seasonal weakness into profit opportunities, including:

• The patterns that have historically triggered the sharpest moves in September and October
• Bullish and bearish setups flashing now, with timing signals designed to target triple-digit returns
• How I structure each trade for maximum upside while keeping risk tightly controlled
• The very next trade idea I’m preparing, revealed live before the pattern takes off

Reserve Your Free Spot Now

Most traders see the year’s weakest season as a danger zone. I’ll show you why it can be the most profitable.

Editorial content from our expert contributors is intended to be information for the general public and not individualized investment advice. Editors/contributors are presenting their individual opinions and strategies, which are neither expressly nor impliedly approved or endorsed by Benzinga.

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