Microsoft Director Just Dropped $2M (while everyone else panics)

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While everyone’s running away from Microsoft like it’s got the plague, Director John Stanton just bought $2 million worth of the stock.

That was February 18th. 5,000 shares at $397.

Now, directors don’t usually put their own cash on the line unless they know something. And this comes just a few months after Bradford Smith, the Vice Chair, showed us a masterclass in timing.

Smith bought 3,842 shares back in April at $377 when nobody wanted to touch this thing. Then he rode it all the way to $520 and sold 38,500 shares in November at $518 – right at the peak. That’s $20 million he got out right before this mess started.

The stock’s down 23% since his sale. You think that’s a coincidence?

Microsoft is trading at 25x trailing earnings. Six months ago, it was 37-44x. Same company, same fundamentals, just a hell of a lot cheaper.

Revenue’s still growing 16-17%. Net margins are still 39%. They’ve got a $625 billion AI backlog they can’t even fill fast enough.

But everyone’s panicking because Azure “only” grew 39% and they spent $37 billion building out AI infrastructure. Since when is 39% growth disappointing?

insider buying msft

Is This A Blood In The Streets Moment For MSFT?

About a third of this selloff comes from what they’re calling the “SaaS apocalypse.” This idea that AI agents are going to kill all software companies.

Complete nonsense.

Microsoft isn’t getting disrupted by AI – they’re building the damn thing. While everyone else worries about being replaced, Microsoft owns the infrastructure powering the whole revolution.

Look, I’ve been doing this for 30 years. Executives sell for a million reasons – taxes, diversification, buying a house. But when they buy with their own money? That’s conviction.

And when you get a pattern like this – Smith timing his exit perfectly at $518, then a director stepping in at $397 – that’s telling you the smart money sees value where everyone else sees disaster.

The pattern’s always the same: mainstream panics, smart money accumulates.

Your Action Plan

Microsoft at $400 isn’t a broken company. It’s a $62 billion cash machine on sale because everyone’s terrified of headlines they don’t understand.

The talking heads will tell you to run. That this time is different. That AI is killing everything.

Do exactly the opposite of what they’re saying.

When insiders sell at $518 and buy at $397, they’re showing you where the real value lives.

These are exactly the contrarian setups we track in the War Room – where technical levels meet insider conviction and the crowd's positioned dead wrong.

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