In Major League Baseball, the 40/40 Club is an exclusive group of players who are the only ones to have achieved both 40 home runs and 40 stolen bases in the same season.

The first player to achieve this milestone was Jose Canseco in 1988 as a member of the Oakland A’s – back during the “Bash Brothers” days with his steroids pal Mark McGwire.

Since then, only three other players have joined this list: Barry Bonds (1996), Alex Rodriguez (1998), and Alfonso Soriano (2006).

Here at All Star Charts, we’ve achieved a little bit of our own 40/40 dynamic as JC celebrated his birthday this week and joined me in the 40+ crowd of awesomeness. Perhaps it’s not quite as exciting as crushing home runs over the wall or swiping second base against catcher Yadi Molina. But I like to think it’s cool in its own way.

As the market continues to test the resolve of both bulls and bears, some bearish setups are starting to trigger.

The team put out their latest Short Report last week and one of the names from that list triggered an entry this morning. And considering that my portfolio of options positions is currently leaning long, I like the idea of establishing some bearish positions to add counterbalance to my holdings.

So let's get right to it.

While certainly not at panic levels, we've been seeing a persistent $VIX holding north of 20, and the last two days we saw it flirt with 25. This signals to me that there is still a bit of uneasiness remaining in the stock market, leftover from the recent correction.

Scanning my books, I noticed my portfolio is a little light on delta neutral premium trades, so we're going to take the recent rise in volatility as an opportunity to add a little diversification.

As always, I take a gander at my list of the most liquid ETF options and look for the ones with the highest implied volatilities right now. And then if the chart suggests some consolidation is in order, that's where I look to strike.

I have one trade that stands out head and shoulders above the rest as my number one F-up. I really screwed this one up.

Financially, it was my best trade of the year. Probably my best trade in several years…

But it still stands out as my worst trade of all time.

This was circa 2013. I had recently moved to Boulder, CO and life was good. New vistas, new friends, new environments, new everything.

And one thing I did which was new for me (at the time), was I had come up with a long-term bullish thesis on a stock. And over the course of a couple days, I wrote up about 5 pages of notes on my yellow legal pad outlining exactly how I’d play my bullish thesis using options.

To quote Steve Strazza: "When commodity stocks go, they go!"

This pretty much sums up the talk we had this morning when coming up with today's trade idea.

We were looking across the strongest sectors and hunting for opportunities to get involved. One challenge we were having is many of the stocks we liked had either already had a big move and we'd be chasing, earnings were on deck in less than a week, or the options chains were too thin for us to get good fills.

Finally, after some searching, we found a name that made sense. And it was one I wasn't familiar with.

No, not Santa. He already came and went.

JC came to Boulder yesterday (where I Iive) and we were able to get together to enjoy a late dinner. It was a great opportunity to reflect on how far we’ve come and what we’ve already accomplished.

All Star Charts launched about 13 years ago. And we launched All Star Options nearly four years ago.

During this time, we’ve seen big bull runs, panic-inducing corrections, and everything in between.

But the one constant has been

I love when the team feels a little "frisky" and hunts for "speculative" ideas. There's nothing that gets the creative juices flowing more than getting outside the wheelhouse a bit, looking for new experiences.

This lead them down the path of picking through the wreckage in Chinese stocks.

In the recent Monthly Candles Strategy session (find the charts here), JC highlighted a couple names in China that are offering speculative opportunities for those willing to step boldly where most bulls are too sheepish to look.

As options traders, we too can join the party. But we can minimize the risk better while still participating if the speculators have their way.

The team put out a piece this week titled Shorting the Long End of the Yield Curve.

I can't pretend to understand the first thing about interest rates, how or why they behave the way they do, nor how their moves in relation to each other mean certain things. Thankfully, I don't need to. I just need to follow price.

And right now, price is signaling loud and clear that we need to take a short position in some of these bond vehicles.

I’ve received a few questions from readers about playing bounces in some oversold stocks.

The most recent was Facebook, er… Meta (whatever).

An opportunistic trader hit me with this question:

Is anybody interested in taking a position in these heavily discounted calls in $FB today?

Discounted? Au contraire, mon frère.

Shares of $FB stock may be “discounted” after getting shellacked to the tune of -26% or so. But there are no discounts to be found anywhere on the options chain.

We're buying the $CVX January 2024 150-strike call options. Yes LEAPS!

Check out our short video with the thought process behind this trade:

[10/19/23: updated stop to 155]

We're taking a Leap here.

The overwhelming majority of options trades we put on at All Star Options tend to be structured in a way to participate in moves that should take place within 2-8 months. The shorter duration trades are usually trades where we are net short premium (naked puts, short strangles, bear call spreads, etc), whereas our longer-term trades tend to be ones where we are net long premium at attractive prices (in volatility terms).

Today, we're doing something we've never done here. We're making a long-term bet utilizing LEAP options.

"LEAP" is an acronym for Long-Term Equity Anticipation Securities. Essentially, this means we're taking a position in options that have greater than a year until expiration.

If you were on the @allstarcharts twitter SPACES chat this morning (every trading day at 11:30ET), you heard us riffing on today's trade.

I was chatting with an All Star Options member this morning and he asked me a very insightful question:

“Sean, I’d be very interested in your thoughts on why you choose not to make a trade in certain setups?”

He went on to elaborate that he’d like to know the things I look for that are possible “red flags” that prevent me from pulling the trigger in otherwise good stock setups.

The overwhelming majority of trades I put on for All Star Options subscribers are in stocks that the All Star Charts team has identified as stocks we want to be in (either long or short).

The most common reason I won’t pull the trigger is