Closed Holiday Trade Alert for +$550 "Don't Try This at Home"
While I was watching the San Diego Padres lose the game. My Trade made $550
Took the /ES naked call off for +$550 (51% of max in 9 hours) We got lucky. We got paid fast. We took the win. No need to wait overnight.
Why We Closed Instead Of Waiting For The Rest
The full max profit on this trade was $1,075 if /ES expired below 7560 tomorrow. We took $550 — about half of that — and walked away. Here’s the math behind the decision:
We already had 50% of max. Our standard rule across the systematic book is to take profits at 50% on short premium. Even though this trade was a rule-breaker on the way in, the exit discipline still applies. Once you’re at 50%, you’ve already captured the part of the trade where the risk/reward was working in your favor. The remaining 50% requires holding through an overnight session in a thin holiday market, on a naked call, with unlimited tail risk above the strike.
Risk/reward flipped against us. At open, we were collecting $1,075 with maybe $4,000-5,000 of realistic downside risk if /ES gapped 50-80 points overnight. After 9 hours of decay, we were now risking that remaining $525 of profit against the same unlimited upside tail. The math gets worse as decay extracts the easy premium.
It was a rule-break to begin with. Holding a rule-breaking trade overnight would be compounding the rule-break. Closing it intra-day, even at a partial win, restores discipline.
50% in 9 hours on a 1-DTE trade is a great outcome. Annualize that and the math is silly. Take it.
The Honest Truth
We got lucky.
Let’s not dress this up. /ES traded sideways-to-slightly-down for most of the holiday session. The market gave us almost no real test. The trade worked because nothing happened — not because the analysis was clever.
Had /ES gapped 30 points higher at any point, we would have been sitting on a $1,500-2,000 paper loss, watching naked call delta accelerate against us, with cash markets closed and limited ability to manage cleanly. The fact that didn’t happen is not a vindication of the strategy. It’s a reminder that unlimited-risk strategies can pay you 60 times in a row and then take it all back on trade #61.
Two real lessons from this round-trip:
1. Size discipline saved us. One contract on a $1M+ P1 portfolio is roughly 0.1% notional. If we’d been wrong, the loss would have been annoying — not a portfolio event. If you take nothing else from this trade, take this: the size you use to break a rule has to be the size you can afford to lose entirely. That’s the only honest way to “break a rule.”
2. Speed of profit ≠ quality of decision. Making $550 in 9 hours feels great. But the speed of the win doesn’t validate the entry. The entry was emotional. The exit was disciplined. That asymmetry — emotional in, disciplined out — is how you stay in the game over decades.
Where We Are Now
Position: flat on the /ES naked call leg.
P1 portfolio: back to its pre-Memorial-Day Greeks profile, plus +$550 cash.
We’ll re-engage with the systematic book on Tuesday’s open. Real setups only.
Real-Life Footnote — The Padres, A Lobster-Dog, And $160 Worth Of Memorial Day
For full transparency: this trade actually became a winner while I was sitting at a San Diego Padres game. That was the Memorial Day plan all along — futures order in the morning, ballpark in the afternoon, watch theta do its job from the stands.
I also tried something new at the park: a Hot Dog + Lobster Roll combination. A “Lobster-Dog,” if you will. And honestly? Amazing. I’m a believer.
The problem: one Lobster-Dog and a beer for two people, with tip, came out to $160 plus. Which means a single round of ballpark food and drinks ate up almost half of today’s $550 profit.
So if you want the real picture: nine hours of holding unlimited tail risk on a naked /ES call netted me $550, and the Padres took $160 of it back in roughly twelve minutes at the concession stand.
Was it worth it? The Lobster-Dog was excellent. The trade worked. The Padres did their thing. I’d call that a successful Memorial Day.
Teaching Takeaway
You don’t have to win the whole hand to win the trade.
The temptation when something is working is to hold for more. The temptation when something is dangerous is to hold and hope. Both temptations lose money over time. Discipline lives in the moments when you’ve already won — and you’re choosing to lock it in rather than press it.
Tomorrow morning, that 7560 call may expire worthless and we’ll “leave $525 on the table.” Or /ES gaps up 40 handles and the contract trades to $50 — and the trader who held would be down $1,500-2,000. We don’t know which. We don’t need to know. The 50% rule eliminates the question.
That’s the whole point of having rules.
— TonyR & TonyB Grow Your Pile
Disclaimer
This trade alert documents the exit of a previously-disclosed trade that violated our published rules on naked short calls. The $550 profit is not a recommendation to replicate the structure. The same trade could just as easily have produced a $2,000+ loss had the market moved against us during the holiday session.
We took the position in size we could afford to lose entirely. We exited at the standard 50% profit target. Neither of those mechanics turns a rule-breaking trade into a strategy you should adopt.
Grow Your Pile is educational content only. Nothing in this alert constitutes investment advice or a recommendation to buy, sell, or hold any security or derivative. Options and futures trading involve substantial risk and are not suitable for all investors. Past performance does not guarantee future results. Trade your own portfolio at your own risk and within your own risk tolerance.
Closing alert published Memorial Day evening, May 25, 2026. Entry: this morning at 9:50 AM. Exit: 6:31 PM. Round-trip: 9 hours. Net: +$550 (51% of max profit). Position flat.