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Welcome back to The WOLF Letter. Markets just wrapped a strong and strange month.

Here is what actually moved, what it means, and where to look as jobs week begins.

Let's Get Into It.
 Markets Weekly · May 29, 2026
S&P Hits A Record.
8 Of 11
Sectors Fell In May.

Dell ripped 30% on $16.1B in AI server sales, yet most sectors finished May red. Plus oil cracks on a 60-day Iran ceasefire and Anthropic eyes a $900B raise.
S&P 500
7,581.59
+1.45% WK
Nasdaq
27,013.02
+2.54% WK
Dow
51,062.80
+0.96% WK

Two things happened this month, and they do not fit together. The S&P 500 closed Friday at a record 7,581, the Nasdaq capped an 8% May at its own all-time high, and yet eight of eleven sectors finished the month lower. The index is green. Most of the market is not.

The split comes down to one trade. Information technology rose about 16% in May and the SOXX semiconductor index climbed 24%, while most sectors outside AI leaned lower. Dell's earnings blowout Friday was the exclamation point. Here is the week, and the tell underneath it.
 The Rundown

Five Stories
That Moved
The Market.
01
Earnings › Dell's AI-Server Blowout

Dell reported $43.8B in quarterly revenue and EPS of $4.86 against a $2.96 estimate, then raised its full-year guidance. The line that mattered was AI servers at $16.1B, up 757% from a year ago. The stock jumped roughly 30% Friday and added an estimated $62B in market value, pulling the rest of the AI hardware chain higher with it. Dell is now the clearest sign that the AI trade is widening beyond chips into servers, storage, and the full buildout.
02
AI Infra › The Trillion-Dollar Club Keeps Growing

There are now 14 public companies worth more than $1 trillion, led by Nvidia near $5.2T, Alphabet at $4.7T, and Apple at $4.5T. Micron crossed $1T for the first time this month and AMD topped $800B, both riding the same AI demand. The concentration cuts both ways: it is why the indexes keep printing records, and why so much now rides on a handful of names.
03
Oil › A 60-Day Ceasefire Sinks Crude

US and Iranian negotiators agreed to a 60-day framework to extend the ceasefire, pending final sign-off, with hopes the Strait of Hormuz reopens. Crude fell on the news: Brent settled near $91.68 and WTI near $87.86, leaving Brent down about 19% from the end of April, its steepest monthly drop since 2020. Lower oil cools one of the Fed's last inflation headaches, which is part of why equities liked it.
04
AI Capital › Anthropic Closes In On A $900B Valuation

Google's $10B investment in Anthropic, made at a $350B valuation, is already worth more than $25B on paper as the AI lab lines up a new round at a reported valuation north of $900B. The read-through is the one driving the whole tape: capital is chasing AI infrastructure and the model layer fast enough to keep resetting the comps. Even AWS margins inflected last quarter on customer spending through Anthropic's models.
05
Fintech › Robinhood Hands The Trades To An AI

Robinhood unveiled AI agents that can scan prices, monitor availability, and place trades and purchases on your instructions, with 3% cash back on the card side. The pitch is a market that runs itself while you sleep. Which raises the obvious question: if the trades never stop, why should the venue?
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 The Play · Long Read

Watch Breadth,
Not The Index.

The headline number is doing a lot of work. The S&P 500 rose about 5.3% in May and closed the month at a record, but underneath that green print, eight of eleven sectors actually fell.

When an index climbs while most of its sectors decline, the rally is being carried by a few names. Right now those names are AI hardware, semis, and mega-cap software, and almost nothing else.

01 · What The Tape Is Hiding

Information technology gained roughly 16% in May while the SOXX semiconductor index ran 24%. Strip those out and the month looks flat to lower. That is the definition of narrow leadership, and it is why a single report like Dell's can swing the whole tape.

02 · Why Goldman And The Bears Both Have A Point

Goldman just raised its year-end S&P 500 target to 8,000 from 7,600, betting the AI engine keeps pulling. The other side of the table sees a crowded trade where too much rides on too few balance sheets. Both can be right until breadth resolves the argument.

03 · The Tell To Watch

Next week is jobs week: JOLTS Tuesday, ADP Wednesday, ISM Services Wednesday, and the jobs report Friday. If the labor data cools and money rotates out of mega-cap tech into the other ten sectors, the rally gets a second engine and breadth heals. If tech keeps carrying it alone, you are in a narrower market than the record highs suggest. The tell is the equal-weight S&P against the cap-weight S&P. Watch that spread through jobs week.
Tactical Close · Before Year-End

While you wait on the data, one housekeeping move. The 2026 HSA contribution limits are $4,400 for self-only coverage and $8,750 for a family, plus a $1,000 catch-up at age 55 and older. An HSA is one of the only accounts with a tax deduction going in, tax-free growth, and tax-free withdrawals for qualified medical costs. If you have an eligible high-deductible plan and the cash flow, it is rare triple-tax-free space worth using before December.
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 Next Issue · Monday

Monday: Jobs Week Kicks Off, Jensen Takes The COMPUTEX Stage, And This Week's WOLF Pick.
Built For
Wolves.
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WOLF Financial publishes The WOLF Pick for informational and educational purposes only. Nothing in this newsletter constitutes financial advice or a recommendation to buy or sell any security. Always do your own research before making investment decisions.

The research and analysis referenced in this edition was prepared by independent third-party sources and shared with WOLF Financial for informational and educational purposes. It does not constitute a recommendation or endorsement by WOLF Financial. Always do your own research before making investment decisions.

Disclosure: This content is a paid partnership with Vest Markets. This information is for informational purposes only and is not investment advice. Vest Markets is a WOLF Financial partner.