Why I Hunt Assignment on TSLL While Everyone Else Runs From It

Jack Carter | January 27, 2026

🚨 I’ll be live at 11:30 AM ET with Jeffry Turnmire for Market Masters🚨
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Some folks treat assignment like a four-letter word.

Not me.

When it comes to Direxion Daily TSLA Bull 2X Shares (TSLL), I’ve found something most traders miss — getting assigned either direction has been a gift. 

I just keep selling those four puts, and the cycle keeps paying over and over. 

It’s simple, it’s repeatable and it’s built around the stock’s natural rhythm.

Every time I get it called away, it’s been a gift. 

Every time it’s been put to me, I could sell it for a buck more the next Monday.

That’s not luck. That’s the setup.

TSLL closed recently at $18.72, and I got assigned around $18.50. Was I upset? 

Not even a little. Because I know what comes next — I’ll be able to buy it back lower and start the whole cycle again.

The Assignment Cycle That Keeps Paying

Here’s the pattern I’ve been running:

I had TSLL assigned to me at $18.50 and sold it at $19.43. Clean profit.

Then I had it taken away from me at $18.50, and I was able to buy it back lower.

Back and forth. Week after week.

There are different ways to play this. My Market Masters co-host, Jeffrey Turnmire, has done it super clean in one account without ever touching the stock — rolling and managing the options themselves. That works.

But my approach is different — I sell a little closer to the money because I like to get assigned. I like to have it put to me, and I like to have it called away.

That doesn’t mean I’m reckless. I tend to roll, and I pay attention to the pennies — which may or may not actually be pennies — because they add up. 

That’s part of the game. That’s part of managing the trade.

And honestly, I just love trading this stock. The volatility creates opportunities most people are too cautious to take advantage of. They’re afraid of assignment. I’m hunting it.

Wednesday’s Tesla Earnings Discussion

We’ve also got a big show this Wednesday focused entirely on Tesla (TSLA) earnings. It’s going to be an important one because the narrative has got to get away from electronic vehicles and into robotics.

When China’s pumping out the BYD car practically free, they’re not gonna let TSLA compete in China on EVs alone. 

The growth story has to shift, and if it does, TSLL becomes even more interesting as a trading vehicle.

But whether the narrative shifts this week or not, I know one thing for sure — this is a stock I love trading.

The assignments keep coming. The premiums stay juicy. And the weekly cycle keeps paying.

That’s how I’m playing it.

Trade well,

Jack Carter
Jack Carter Trading 

Follow along and join the conversation for real-time analysis, trade ideas, market insights and more!

Important Note: No one from the ProsperityPub team or Jack Carter Trading will ever contact you directly on Telegram. 

*This is for informational and educational purposes only. There is inherent risk in trading, so trade at your own risk. 

PS. Still Don’t Know How I’m Going after Tesla?

How would you like me to walk you through my special weekly setup on Tesla?

I’ve deployed this setup 85 times over the past two years, all while the stock was either rocketing to new highs or dumping to disappointing lows.

But despite the crazy price action, I’ve won eight out of every 10 trades on average.

And this week, I’m going after the first Tesla trade of the year using this setup.

I can’t make absolute guarantees when it comes to trading, of course…

But I want to clue you in on why it’s the top strategy for trading Tesla in 2026…

As well as how to take this week’s trade.

Get My Tesla Playbook for This Week’s Trade

Disclaimer: We develop tools and strategies to the best of our ability, but no one can guarantee the future. There is always a risk of loss when trading. Past Performance is not indicative of future results. On the live trades the results are an 80% win rate from 4/05/23 through 1/20/25 and the average return per trade (winners and losers included) is 22.70% per trade in a 6 day average hold time with an average winner of 52.76%.

6 Reasons Your Account Keeps Bleeding

Pods Admin | December 14, 2025

>>> I’ll be live with Graham Lindman this Sunday at 7 PM ET for the Upside-Down Options Summit — we’ll reveal the discovery that boosted win rates, and show how you can take your first trade Monday morning, Click Here to join <<<

I get asked all the time why so many option traders blow up their accounts.

The answer isn’t complicated. 

It’s not some hidden Wall Street secret or proprietary algorithm you need to crack.

It’s simpler than that — and harder to fix than most people want to admit.

  1. They don’t have a system.
  2. They don’t have discipline.
  3. They put too much on the line with every trade.
  4. They take too much risk.
  5. They don’t put probability on their side/take advantage of time decay.
  6. They take reckless trades.

And then there are three things that actually make traders successful — patience, discipline and accountability. Most traders never develop any of them.

The Guy Who Had It All — Then Lost It

I knew a young guy, early 30s, who traded professionally for about a year. One time, he had a month where he made around $30,000. That’s a damn good month when you’re trading on your own.

So I asked him about his strategy.

Turns out, 100% of his approach was buying high-risk calls. That was it. No hedges. No selling premium. No time decay working in his favor. 

Just swinging for the fences every time.

The last time I talked to him in person, he told me he wished he could be on the sell side of options — that he wished he had enough money to do that. 

But he was taking such insane risk that he lost it all and had to go get a regular job with a W-2 attached to it.

He’d take all of his money — $25K or whatever — and just take wild risks buying calls with it. 

One bad week and it was over.

Meanwhile, you can start with a grand on the sell side and do great — if you actually commit to a system and proper risk management.

The Lambo Lie

Here’s the other thing that kills traders: expectations.

This is so much work. It’s not exciting, like they say on the internet. I don’t have a Lambo in my driveway.

People start trading with visions of quick riches. They see the highlight reels. They hear about the guy who turned $500 into $50,000 on a single trade. They think that’s the norm.

It’s not, and this is the kind of mindset that gets people in trouble…

What am I doing wrong? I started with a grand, and I still don’t have a Lambo. 

The real game is boring. It’s disciplined. It’s methodical. It’s about stacking small, high-probability wins and managing risk so the inevitable losses don’t wipe you out.

If you can’t accept that, you’re going to end up like that guy I knew — with a great month or two in your rearview mirror and nothing left in the account.

Stop swinging for the fences. Stop risking everything on one trade. Stop chasing the excitement.

Build a system. Manage your risk. Let time decay work for you. And stay in the game long enough to actually win.

If it’s boring and you’re making money, then you’re doing it right. 

Trade well,

Jack Carter
Jack Carter Trading 

Follow along and join the conversation for real-time analysis, trade ideas, market insights and more!

Important Note: No one from the ProsperityPub team or Jack Carter Trading will ever contact you directly on Telegram. 

*This is for informational and educational purposes only. There is inherent risk in trading, so trade at your own risk. 

P.S. My Upside-Down Options Summit kicks off on Sunday

What if we showed you a brand new way to target daily income on options?

An unconventional setup that went unbeaten across 14 LIVE trades during one of the market’s most chaotic stretches this year…

This Sunday, I’m going live with Graham Lindman to reveal a never-seen-before setup to target daily cash from the options market.

I’m calling it the Upside-Down Options Summit.

Everyone who tunes in will see exactly how I built the entire setup from scratch… plus how to get in on the first trade as soon as Monday.

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