THE DEAN’S LIST: The Maxim That Refuses to Die

All three major indexes are at simultaneous all-time records. The S&P just put together its ninth straight winning week. The Nasdaq finished May up 8%, its best month since 2023. Dell had its best day on record. And a tentative Iran ceasefire framework just sent oil tumbling.

Before you assume the rally never ends, pull up the Single-Digit Millionaire portfolio. Look at how it is balanced. Rallies rarely warn you before they pause. A portfolio that works in both directions does not need a warning.

Dean’s note:
You have heard it your whole investing life. "Sell in May and go away."

It rhymes. It is catchy. And it has been wrong for 75 years running.

The funny thing this year is that I have barely heard a peep about it. When the cliche goes quiet, the cliche is usually about to be even more wrong than usual.

Here is the actual record. I pulled every May-October period for the S&P 500 since 1950. Seventy-six windows. The average summer return was 3.05%, and the market was positive in 2 out of every 3 years. Sitting out that window has cost investors real money for three quarters of a century.

Yes, May-October is the weakest six-month stretch. But "weakest" is not "negative." November-April averaged +5.96%. Both halves of the year have, on average, paid investors to stay in their seats.

Now narrow the lens to 2026. The S&P is up 10.4% year-to-date through May 28, and we are in a midterm election year. When the market is already up more than 5% through May, the summer that follows has averaged +5.68% and been positive 80% of the time. The only ugly outlier was 1987, which had nothing to do with summer seasonality. Filter to midterm-hot-start years specifically, and you get six historical cases. Five positive. One mild loss. Average summer return: +7.89%.

Then comes the kicker. The post-midterm November-April window is the single strongest seasonal pattern in the equity market. Nineteen for nineteen since 1950. Average +12.6%. There is no other six-month seasonal setup with a hit rate like that, and we are sitting right at the front door.

None of this means back up the truck. The 10-year yield is at a one-year high. The 30-year is near 5%. SpaceX is about to flood the market with the largest IPO in history. And the Iran ceasefire that lifted oil off $114 still has not been signed. Those are the real risks this summer. The seasonal argument for selling, the one your brother-in-law brought up at the Memorial Day cookout, is the weakest argument in the room.

The maxim is wrong. The math is the math. Stay calm. Stay invested. And ignore the rhymes.

A short week with one giant headline buried inside it. Here is how it played out:

Monday (May 25): Markets closed for Memorial Day. Over the long weekend, Iran conducted strikes in the region. By Tuesday morning, futures pointed higher anyway. Risk appetite refused to flinch.

Tuesday (May 26): The S&P gained 0.61% to a fresh record of 7,519. The Nasdaq jumped 1.19% to 26,656, also a record. The Dow slipped 0.23% as AI and tech ran while old-economy names lagged.

Wednesday (May 27): The Dow set a record while the S&P and Nasdaq paused. Chip stocks pulled back. NVIDIA fell 2.37%. Snowflake reported earnings after the bell and announced a $6 billion partnership with AWS.

Thursday (May 28): The day that did everything. Axios reported that U.S. negotiators led by Steve Witkoff and Iran's Abbas Araghchi had reached a tentative 60-day ceasefire framework. The deal would require Iran to remove all mines from the Strait of Hormuz within 30 days and would lift the U.S. naval blockade in proportion to the restoration of commercial shipping. Wall Street added roughly $350 billion in market value within fifteen minutes. All three indices closed at simultaneous records. The S&P is at 7,563. Nasdaq at 26,917. Dow at 50,668. Snowflake surged 36.5%, its biggest day ever. The same morning, the data underneath was less kind. PCE inflation hit 3.8% year-over-year, the hottest in three years. Q1 GDP got revised down to 1.6%. Real disposable income fell for a third straight month. Six different Fed officials publicly warned that rate hikes remain on the table. Markets ignored it all and bought the AI trade harder.

Friday (May 29): The ninth consecutive winning week was completed. The S&P added 0.22% to close at 7,580, a fresh record. The Nasdaq gained 0.2% to 26,972, also a record. The Dow rose 0.72% to close above 51,000 for the first time in history. Dell Technologies surged nearly 33% on a Q1 beat and raised guidance, its best single day on record. Micron +5%. Qualcomm +3%. President Trump told reporters he needed "a couple of days to think" before signing the Iran framework. Oil eased to $91 Brent. Bitcoin slipped 3%. The VIX dropped to 15.3.

On Thursday, Axios reported that the United States and Iran had agreed to a 60-day ceasefire extension. The framework would guarantee unrestricted shipping through the Strait of Hormuz, require Iran to remove all mines from the waterway within 30 days, and lift the U.S. naval blockade in proportion to the restoration of commercial traffic. Witkoff and Araghchi led the negotiation.

Wall Street added roughly $350 billion in market value within fifteen minutes. Oil dropped sharply. Bond yields eased. And then on Friday, the President said he needed "a couple of days to think" before signing.

Brent has now fallen from $114 a few weeks ago to about $91. If the framework holds and the mines come out, oil moves toward the curve that has been screaming the truth all year. Futures for 2027 have been in the high $60s since week one of the war. The market has been right about the direction the whole time. It is finally right about the timing, too.

Dean’s note:
I have watched many last-mile diplomatic decisions over the years. The pattern is almost always the same. Frameworks get announced. Both sides find one more issue to negotiate. The signature gets delayed. Markets get nervous. Then it gets signed, or it does not.

The "couple of days to think" line is not the red flag people think it is. It is the negotiation tactic that surfaces in almost every serious agreement. The thing actually worth watching is the mine-removal clock. Thirty days from signing. Shipping data tells the truth long before any press release. Watch ships, not statements.

Let me lay out the actual numbers behind "Sell in May," because the maxim survives mostly because nobody bothers to look them up.

Since 1950, the S&P 500 has had 76 May-October periods. The average return was +3.05%. The market was positive in 2 of every 3 of those summers. The maxim assumes that giving up that 3% is somehow risk management. It is not. It is leaving money on the table 65% of the time.

November-April averaged +5.96%, so summer is the weaker half. "Weaker" is not "lose money." Both halves, on average, rewarded the patient investor.

Then comes our specific setup. S&P up 10.4% year-to-date. Midterm election year. Hot start. Six historical comparables since 1950. Five positive summers. One mild loss. Average summer return: +7.89%.

And the kicker that ought to make every investor sit up. The post-midterm November-April window is 19-for-19 since 1950. Average +12.6%. The strongest seasonal pattern in the equity market. We are sitting at its front door.

Dean’s note:
None of this is a guarantee. History never reads from its own script word for word. But when somebody tells you to sell in May, they are arguing with a 75-year track record of being wrong. The risks this summer are real. They are also not seasonal.

The 10-year near a one-year high is real. The 30-year near 5% is real. The SpaceX IPO flood is real. Iran's signature getting delayed is real. But none of those is a reason to time the calendar. There are reasons to be selective about what you own, not whether you own anything at all.

Quietly, away from the day-to-day records, something significant happened this month. The technology sector officially overtook energy as the best-performing sector in the S&P 500 year to date.

Stop and think about that for a second. We are in a year that began with an oil shock so severe that the Strait of Hormuz suffered its first near-complete stoppage in recorded history. Brent peaked at $114. California gas hit $6. Energy should be the layup trade of 2026. For most of the spring, it was.

But tech caught up. Then it passed energy. And it now leads by a meaningful margin. Why? Azure grew 40% last quarter. Google Cloud grew 63%. Snowflake just signed a $6 billion AWS deal. Dell reported its best quarter ever, driven by demand for AI servers. Micron's high-bandwidth memory chips are sold out through 2026.

Dean’s note:
This is a signal worth holding onto for the rest of 2026 and into 2027. When AI infrastructure beats an oil shock in the year-to-date sector rankings, the market is telling you which demand curve is steeper.

Structural compute demand has now overtaken cyclical oil demand, even during an active war. Energy still matters. Geopolitical risk still matters. But the dominant economic narrative of this decade is being written in transistors and data centers, not in barrels. Position accordingly. Just do not overpay for the shiny version of it.

Friday's headline number was Dell, up nearly 33%. Best single day in the company's 41-year history.

Dell is not a stock that gets much love on tech Twitter. It is not Nvidia. It is not the AI poster child. It is a computer company that sells servers, storage, and laptops. The kind of business influencers ignore.

Then Dell reported. Revenue beat. Earnings beat. AI server backlog up sharply. Full-year guidance raised meaningfully. Dell makes the boxes that hold the chips that run the workloads. When AI capex booms, Dell wins by default.

Dean’s note:
There is a lesson in Dell's quarter that gets lost in the celebration of the move. "Boring" is not a bad word in investing. It is often the best word. The companies that quietly deliver beat after beat, in industries everyone thinks they understand, are the ones that compound steadily over decades.

Dell did not have its best day on Friday because the market suddenly discovered the company. It had its best day because the company kept doing what it always does, just better, at a moment when its products mattered more than they have in years. The flashy AI names get the headlines. The quietly excellent businesses often deliver better long-term returns. Watch the ones nobody is talking about.

Stay invested. Stay selective. And ignore the cliches.

A short week with three record highs, the strongest May in years, Dell's best day on record, and a tentative Iran framework that still needs a signature.

•  "Sell in May" has been wrong for 75 years. Seventy-six May-October windows since 1950. Average +3.05%. Positive 2 of 3 years. The maxim is a rhyme, not a strategy. When the cliche goes quiet, history says it is usually about to be even more wrong than usual.

•   The post-midterm Nov-April window is the strongest seasonal pattern in equities. 19 for 19 since 1950. Average +12.6%. No other six-month setup has that hit rate. We are at its doorstep. Take note.

•   Tech has overtaken energy as the best-performing S&P sector year-to-date. In a year that started with the worst oil shock in modern memory. AI infrastructure beat a war. That tells you which curve is steeper. Position accordingly.

•  The Iran framework is the most important development of the week, full stop. A signed deal sends oil toward its 2027 futures curve (high $60s), pulls inflation down, and gives Warsh's Fed room to act. A failed deal means oil bounces and the bond market gets uglier. Watch ships, not statements. Mine-removal clock is 30 days from signing.

•   Dell up 33% Friday is the boring-winner story of the year. Beat. Raise. AI server backlog strong. Boring is not a bad word. The companies in industries that everyone thinks they understand are often the best long-term compounders.

•   All three indices at simultaneous records is the headline. PCE at a three-year high, GDP revised down, six Fed officials warning about hikes, Bitcoin slipping 3% on a record day for stocks. Those are the footnotes. Footnotes eventually become text.

•  SpaceX, OpenAI, and Anthropic are still lining up the largest IPO wave in market history. Not on the calendar yet, but on the horizon. The mechanical pressure of trillions in new equity is still building. It just is not priced in yet.

•  Keep contributing to your 401(k). $24,500 limit. $35,750 super catch-up if you are 60-63. Seasonal math, structural earnings, and the discipline of dollar-cost averaging all point in the same direction. Show up every paycheck. The rhyme is not in charge.

Here is where I land. The summer ahead is not the summer to sell. The math says stay invested. The seasonal setup says stay invested. The AI cycle says stay invested. But the bond market and the inflation data suggest being selective. Both messages are true at the same time. The investor who hears both and acts on both wins the next twelve months. The investor who only hears one of them probably does not.

Stay calm. Stay invested. Stay selective. And do not let a 75-year-old rhyme talk you out of a 75-year track record of being wrong.

- Dean

P.S. The number that sticks with me this week: 19 for 19. That is the record of the post-midterm November-April window in the S&P 500 since 1950. Nineteen consecutive instances. All positive. Average return +12.6%. There is no other seasonal pattern with that kind of hit rate over six months. We are sitting right at its doorstep. When somebody tells you to sell in May because it rhymes, the right response is to ask which other 19-for-19 pattern they would rather bet against. Usually, there is silence.

And one more thought. Robinhood quietly unveiled "Agentic Trading" and an "Agentic Credit Card" this week. Products that let third-party AI assistants execute trades and make purchases on users' behalf with minimal human involvement. Mizuho raised its price target to $115 the same day. I bring this up because it is the next chapter of the AI story we have been tracking all year. Agentic AI is no longer just about Microsoft Azure or AMD's chip mix. It is now about consumer products that delegate financial decisions to algorithms. Whether that turns out to be wonderful or worrying, we will find out. But it is the kind of structural shift that quietly rewrites how money moves over a decade. Keep an eye on this. It matters more than it currently appears.

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This newsletter is for informational purposes only and does not constitute investment advice. Past performance is not indicative of future results. Consult with a qualified financial advisor before making any investment decisions.