Why I Sold AMZN, MSFT

On Wednesday afternoon (near the lows) I established longs in Microsoft ($MSFT) and Amazon ($AMZN). 

I know Amazon reasonably well, not so much Microsoft (though I was prone to buy it based on Bill Ackman’s recent buy (at much higher levels) in his new publicly traded vehicle ($PSUS).

While I have successfully trafficked/traded Amazon and Microsoft on several occasions — my avoidance of the stocks reflected a generally negative view that those two constituents of Mag7 (as with the others) had morphed from a capital light to capital intensive. That metamorphosis has execution risk, increases the likelihood of lower share buybacks and provides less certainty to the profit stream.

As noted in my Diary yesterday and this morning, MAG7 in the aggregate have been awful performers — and have likely been a source of funds to buy memory and semi stocks.

I aggregated sell-side research reports on both companies last night (as I spent some portion of the evening trading ($SPY)/($QQQ) and concluded in the case of MSFT the above challenges are being exacerbated by continued changes in their AI strategy and positioning. Though I am not an expert on Microsoft, from my perch, MSFT’s estimates might be lowered. 

I am not sure, however, why Amazon has been so weak, but I decided to bale on that as well. I plan on continuing to do my research on the name to get more informed and current. 

From Comments Section last night:

Dougie Kass
11h ago

Sold my AMZN $239.88 adn MSFT $383.06

From earlier:

Loaded Up on Microsoft and Amazon

I bought a ton of MSFT at $378.05 and AMZN at $237.01 in the last 15 minutes of the day.

Position: Long MSFT (M), AMZN (M)

By Doug Kass · Jun 17, 2026, 4:03 PM EDT

Dougie Kass
11h ago

I am not sure I understand the after market ramp = s and p futures +64 and nasdaq futues +401

*taking profits in msft and amazn buys

shorting spy $745.81 and qqq  $732.40

Position: None

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Posted by Doug Kass

Doug Kass is a world-renowned hedge fund manager with decades of experience and success navigating through some of the most turbulent periods in market history. He is known for his time-tested analytical skills and ability to look past the current noise and herd mentality. On TheStreet Pro, Kass provides frequent market commentary and investing ideas for active investors throughout each trading day in Doug’s Daily Diary. He also serves as president of Seabreeze Partners Management Inc. Previously, he served as a senior manager at Omega Advisors, a $6 billion investment partnership. He co-authored a book with Ralph Nader and the Center for the Study of Responsive Law called “Citibank: The Ralph Nader Report” and can be found as a guest host on CNBC's "Squawk Box." A Note from Doug: Current strategies and actionable trade ideas -- all on one dynamic platform built exclusively for active trades. From sudden sell-offs to sudden spikes, TheStreet Pro arms you with crucial analysis -- at a rapid fire, professional pace -- to help you make sound trading decisions -- every day, every hour, and every minute. Join me and my team of professional traders for unique perspectives and breakthrough investment opportunities.

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