To The Moon

Got Called Away On 2,000 Shares. Took Some LEAPS Off The Table. Two Weeks In One Post.

Mathematical Money | May 23, 2026

I skipped last week's post. Honestly because there was too much going on and I wanted to wait until the dust settled before writing about it properly. So this one covers two weeks instead of one.

Two weeks ago I wrote about how the system runs quiet most of the time. I also said the harder weeks were coming and I'd write those too. This is one of those weeks. Maybe two of them.

Let me walk through what actually happened.

The Assignment

MARA pushed from around $12 to $13.55 over the past fortnight. That kind of move sounds great when you're long the stock — and it has been — but I was also short a lot of calls. The ones I was most worried about were the May 15 $10 strikes I'd been holding for a few weeks. With the stock pushing through $13, those calls were $3+ in the money and had effectively no extrinsic value left.

I rolled most of the May 15 stack out in time, paying the difference. But I left some of the $10 strikes too long. On May 15 expiry, 20 contracts went deep in the money and got assigned. That's 2,000 shares of MARA called away from me at $10, when the stock was trading at $13.55.

In dollar terms, the assignment shows up as a realized stock loss on those 2,000 shares — about $15,600. But that's not really the right way to think about it, because over the months I was holding and rolling those calls, the premium they collected was substantial. The honest framing is that I gave up the upside above $10 on those 2,000 shares in exchange for the premium I'd been collecting all along. The full life-of-trade math is roughly break-even to slightly positive on that block of contracts. Not a disaster. Not great either.

The lesson, and I want to be direct about it: I should have rolled those $10 strikes up sooner. By the time I acted, the calls were so deep in the money there was no good roll available — I was just paying near-intrinsic to get out. Next time the stock pushes through a strike level by 20%+, the calls move out the same day. Not next week. Same day.

The Roll Wave

The rest of the May 15 stack got rolled out, and it cost real money.

I closed 100 contracts of $12 May 15 calls at a roll cost of about $6,920. I closed another 70 contracts of $11 calls at a roll cost of about $3,910. Another 35 contracts of $11 calls at about $3,690. Plus assorted smaller pieces. Total MARA call roll cost for the two weeks ran around $16,000 in realized losses.

Where did that money go? Into new short calls at higher strikes, further out in time. The book now has 100 contracts of $13 calls for June 12, 105 contracts of $11.50 calls for June 5, and various $12 and $14 strikes scattered across the next few expiries. The premium intake from those new positions is significant and will decay through June. So the realized loss on the rolls is the price I paid to keep the share position and re-set the strikes higher.

On the put side, the May 22 $9 puts I had open decayed to almost zero — closed all 100 of them for a clean profit of about $2,460. Opened new puts at $11 strike for June 5 (80 contracts). The wheel re-priced upward because MARA re-priced upward.

The Other Side Of The Book

While the MARA leg was getting hit, the SPY leg was paying off.

I took meaningful profits on the SPY LEAPS book over these two weeks. The LEAPS I'd been quietly accumulating since March have been appreciating as SPY pushed into the $720s. On May 18 I closed seven of them. On May 20 and 21 I closed several more. Specific numbers:

- December 2026 $670 call: closed at $100.99, +$4,561 realized

- December 2026 $675 call: closed at $96.53, +$4,629 realized

- December 2026 $705 call: closed at $73.02, +$2,044

- December 2026 $710 call: closed at $69.25, +$2,087 (a second contract: +$1,148 a few days later)

- March 2027 $710 call: closed at $81.62, +$2,166 (a second: +$1,439)

- March 2027 $705 call: closed at $80.31, +$1,618

- March 2027 $715 call: closed at $72.32, +$955

Total SPY realized profit across the two weeks: about $8,880.

Why now? Two reasons. First, several of these LEAPS had nearly doubled from where I bought them. When a long position more than doubles in a couple of months, you take some of it off the table. That's the rule. Second, SPY was approaching levels where I wanted to reduce gross long exposure and reload the short call ladder higher. Mechanical, not predictive — but the discipline still has to be acted on.

The remaining LEAPS book is still substantial. I haven't fully exited PMCC structure on SPY. I've just trimmed it down to a more comfortable size given the rally.

Net Result

The MARA roll losses and the SPY LEAPS profits roughly offset each other on the realized P&L line. Add in the new premium collected from all the re-set short calls and puts, and the book is grinding forward in the same way it has been — just with more activity than usual.

The underlying stock position also benefited from MARA's recovery, and the remaining open LEAPS continued to appreciate. So on a total-return basis the two weeks were positive, even with the assignment loss and the roll costs baked in.

This is the point of running uncorrelated legs. When MARA goes against the short calls, SPY LEAPS work in your favour. When SPY consolidates, MARA premium still grinds. The whole thing is designed so that no single event can take the book apart.

That's the design. Whether it holds in a real drawdown is a different question, and I don't have an honest answer until I'm in one.

What's New

A few additions over the two weeks worth noting:

MSFT LEAPS doubled. Added January 2027 $480 and January 2027 $500 strikes. The MSFT PMCC book is now four LEAPS across multiple strikes and expiries — same systematic ladder approach as SPY, just smaller.

COIN re-entered. Sold a June 12 $225 call and a June 12 $175 put. First active COIN options structure I've had in months. Just one strangle, not a full wheel. Testing the water.

MARA wheel fully re-priced. Short calls now sit at $12 to $14 strikes across May 22, May 29, June 5, June 12 and June 18 expiries. Short puts at $11 strike for June 5, $10 for May 29. The whole structure moved up roughly $2 in strike to match where the stock is actually trading.

The Honest Part

I lost shares I didn't want to lose. I paid real money in roll costs that wouldn't have been necessary if I'd acted faster on the $10 strikes. The LEAPS profits offset most of that, but I'd rather not have needed the offset in the first place.

What the system did right was prevent any single decision from being catastrophic. The assignment was annoying but not portfolio-threatening. The rolls were expensive but kept the share position intact. The LEAPS harvest was disciplined and brought real cash back into the book. None of it required a market call.

What the system asked me to do better was move faster on the rolls. I'll work on that.

If you want the detail on assignment mechanics, LEAPS harvest decisions, or how to size the roll cost against the upside you're preserving — drop a comment below. Faster channels: TikTok and YouTube DMs (Mathematical Money on both) or through trueknot.sg.

Stay disciplined. Size your positions properly. See you next week. 🤙