portfolio

We're Locking in Massive Gains on 2 Holdings After AI Surge

As we get ready for a key Fed policy outcome, we’re also sharing our updated shopping list.

Chris Versace·Oct 29, 2025, 11:05 AM EDT

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SymbolTransaction Type# Shares TradedRecent Price $Shares Owned After Trade% Portfolio

MSFT

Sell

24

$537.75

346

3.25%

NVDA

Sell

135

$210

1,120

4.1%

After you receive this alert, the Portfolio will make the following trades:

Sell 24 shares of Microsoft (MSFT)  at or near $537.75. Following the trade, the Portfolio will own 346 MSFT shares, roughly 3.25% of the Portfolio.

Sell 135 shares of Nvidia (NVDA)  at or near $210. Following the trade, the Portfolio will own 1,120 NVDA shares, roughly 4.1% of the Portfolio.

With shares of Nvidia quickly moving past the $5 trillion market cap level, the first company to do so, the shares have not only pushed past 4.6% of the Portfolio’s assets, but they’ve also landed in an overbought condition. As we discussed in our comments to you earlier on Wednesday, while we are for letting our winners run, past a certain point, we have to stick to our discipline, no matter how unpopular it may be.

That is leading us to ring the register in a modest way with NVDA shares on Wednesday morning, keeping ample skin in the game given what we see ahead. At the same time, we are also taking advantage of the 50% move in MSFT shares over the last few months, as well, to lock in a very small but very profitable slice of that position.

Another factor in this timing is the Wednesday afternoon Fed policy decision outcome. Yes, a 25 basis point rate cut is still expected, but it’s what Fed Chair Powell may say about another rate cut before we close out 2025 that could change things. The updated CME FedWatch Tools shows the market thinks there is an 85% chance of that cut coming in December, but it’s very possible that Powell reiterates the “need to see more data” line he tends to trot out.

There is also the comment we shared with you on Wednesday morning that, while U.S.-China trade tensions are softening, the details of any trade deal announced on Thursday will be what matters most. If you’re thinking there is room to be underwhelmed, we aren’t going to argue with you.

And if we’re wrong, the Portfolio still has more than 7.3% of its holdings in NVDA and MSFT shares, as well as others that will benefit from AI adoption and the ecosystem buildout.

Netting those factors out, we’re going ahead and locking in those gains, which will help rebuild the Portfolio’s cash levels.

As we make this move, we will note our updated shopping list includes shares of SuRo Capital (SSSS) , Labcorp (LH) , Waste Management (WM)  and Welltower (WELL) .

More Pro Portfolio: (updated Oct. 28)

(Please note that we are looking to execute these trades at or near the share price mentioned above. Once the trade is completed, subscribers can see the trade's executed price here. Be sure to toggle the chart to sort by Purchase Date.)

At the time of publication, TheStreet Pro Portfolio was long MSFT, NVDA, SSSS, LH, WM and WELL.