Vice Chair Buys Shares of Magnificent Seven Microsoft—At a Not-So-Magnificent Price

NASDAQ: MSFT • $478.53 (-1.02%) 😅
As of Dec 12, 2025 · 4:15 PM ET
FUNstock Index: 7 / 10 🎯

Microsoft (MSFT), aka The Titanic That Refuses to Sink, just got another jolt of insider confidence — and not from a junior VP looking for press. Nope. The company’s Vice Chair & President, Bradford L. Smith, cracked open his wallet and dropped $1.45 million on MSFT shares at $377.47 back in April.

Brad doesn’t usually impulse-buy stocks. He’s not at Target. So why now? And why at a price that looked “premium enough,” only for the stock to zoom almost $100 higher since?

Let’s dive in — AI-powered snorkels on. 🤿⚡

🔥 Trigger #1: The Insider Buy — When the President Says “I’ll Take 3,842 of Those”

On April 23, 2025, Bradford Smith purchased:

• 3,842 shares

• At $377.47

• Worth ~$1.45 million

• Boosting his holdings to 451,597 shares
  (When your “+1% position increase” is still worth more than small countries, you know you’re living right.)

Insiders buy for one reason:
👉 They think shares will be worth more later.

They sell for 37 reasons (taxes, diversification, yachts, divorces, wanting a yacht after a divorce…), but they buy for one.

Microsoft insiders rarely buy. So when they do, markets listen.

🏦 Trigger #2: Institutions Like the Stock — But It’s Not Overcrowded

Institutional ownership sits around 75.7%, which is high but not “every pension fund in the galaxy owns it” high.

The usual Avengers are assembling:

• Vanguard: 702M shares (9.44% of outstanding shares)

• BlackRock: 592M

• JPMorgan: 318M

• State Street: 300M

• Fidelity (FMR): 210M

• Morgan Stanley, T. Rowe Price, Geode, Northern Trust…

When the smartest money in the world holds MSFT in bulk, it’s rarely a coincidence.
It’s usually a strategy. ⚙️💰

For Microsoft (MSFT)’s Institutional Ownership breakdown, 🔍 see here.

🔮 Trigger #3: Analysts Still Love MSFT Like It’s 2019

The analyst consensus:
Strong Buy → Moderate Buy → Buy The Dip, You Cowards.

Average 12-month target price: $630–$632
That’s a cool +30% upside from today’s price.

And here’s a spicy research note from CFRA:

• Target price: $620

• AI demand “outstrips supply” ⚡

• Commercial bookings: +112% YoY 🤯

• Commercial RPO: +51% YoY

• Azure growth holding steady in the high 30s

• AI tokens per watt per dollar (don’t ask, just nod respectfully)

Wall Street believes MSFT’s AI empire is not only real — it’s scaling like a controlled explosion.

📉 Trigger #4: Shares Are 14% Below ATH

The peak?
$555.45 in July 2025.

Today?
$478-ish.

Not cheap.
Not bubble-level either.
Just... Microsoft being Microsoft: premium, like a hotel mini-bar chocolate bar you buy anyway.

🧠 Trigger #5: Microsoft’s Earnings — Still Printing Cash Like It Found the Cheat Codes

Q3 FY25 results were a fireworks show:

• Revenue: $70.1B (+13%)

• Operating income: $32.0B (+16%)

• Net income: $25.8B (+18%)

• EPS: $3.46 (+18%)

• Microsoft Cloud: $42.4B (+20%)

Highlights:

Productivity & Business Processes 💼

• Office 365 Commercial: +11%

• Dynamics 365: +16%

• LinkedIn: +7%

• Microsoft 365 Consumer: +10%

Intelligent Cloud ☁️

• Intelligent Cloud revenue: $26.8B (+21%)

• Azure: +33% (and +35% in constant currency)

More Personal Computing 🎮

• Windows OEM: +3%

• Xbox content & services: +8%

• Search & ads (ex-TAC): +21% 👀

Microsoft ended the quarter with a small gesture to shareholders:
$9.7 billion in dividends + buybacks.
Pocket change. 💸

 👉 Want the full picture? Dive into Microsoft (MSFT)’s financials here.

🏛️ The Valuation Reality Check: Premium With a Purpose

Is MSFT cheap?
🤣 No.

Is MSFT expensive?
Yes — but reasonably expensive, like a Tesla that still actually works.

Key valuation ratios today (approx.):

• P/E: ~34

• Forward P/E: ~30

• PEG: 1.96

• Price/Sales: 12.2

• EV/EBITDA: 20.7

Microsoft isn’t trading like a sleepy mega-cap.
It’s trading like a mega-cap with:

✔ AI dominance
✔ Cloud #2 position
✔ Office 365 profits on autopilot
✔ Gaming empire
✔ Cash flows that can fund small nations

Still, value hunters will squint.

💙 The Long-Term Bull Case: Why It’s Hard Not to Love (or At Least Like) MSFT

✔ AI Leadership

Azure + OpenAI = the Coke + Mentos of enterprise cloud.

✔ Diversified Business Model

Office, Azure, Windows, LinkedIn, GitHub, Xbox, Enterprise apps…
Microsoft could lose entire divisions and barely flinch.

✔ Massive Free Cash Flow

The company spits out tens of billions per quarter. That fuels R&D, capex, buybacks, dividends — and confidence.

✔ Stability + Resilience

Microsoft has survived every tech cycle since disco.

✔ Dividend Aristocracy

20 years of dividend growth.
Not huge yields, but beautifully reliable.

😬 But Beware: Not Everything Is Sunshine in Redmond

❗ Premium Valuation

Great company ≠ great price.
We personally like it closer to $400.

❗ Capex Explosion

AI = Data centers → Servers → GPUs → Electricity bills → CFO heart palpitations.

❗ Competition Never Sleeps

Google, Amazon, Nvidia, Oracle — the whole tech zoo.

❗ Regulatory Fog

AI + cloud dominance = more governmental “We need to talk.”

💡💡💡 Curious about another deep oil exploration play?
Check our takes on UnitedHealth Group or even Oscar Health.

🎯 Bottom Line

Microsoft remains one of the best businesses on Earth — but even world-class companies can become world-class expensive.

If the stock drifts toward $400 again, the Buy button becomes easier to hit.

Until then?
It's a premium stock at a premium price, with premium long-term upside and premium short-term volatility.

AKA: Microsoft.

⚡ Quick Take / TL;DR

• Insider buy? ✔ +$1.45M

• Institutions in? ✔

• Analysts bullish? ✔

• Fundamentals strong? ✔

• Price cheap? ❌

• Price reasonable? ✔-ish

• FUNstock Index: 7 / 10 🎯

MSFT is a long-term compounder, still pricey, still powerful.
A buy-on-dip legend.
We like it lower — but we like it.

❓ FAQ

📌 Is Microsoft still a good long-term investment?
Yes — it’s one of the strongest mega-caps ever built.

📌 Is MSFT expensive?
Always. Forever. Per tradition.

📌 Is AI really moving the needle?
Yes. Azure growth + AI bookings = monster demand.

📌 Should I wait for a dip?
If you’re patient, history suggests MSFT always gives you one.
If you’re impatient, well… you’re in tech.

👤 About the Author — Frédéric Marsanne

Frédéric Marsanne is the founder of FUNanc1al — part market analyst, part storyteller, part accidental comedian. He blends sharp insights with humor to help readers laugh, learn, and invest a little wiser (or at least laugh while losing less).

This article blends research and entertainment — not prescriptions.
Side effects may include mental turbulence and raised eyebrows.
Nothing here is financial advice.

Always DYOR, resist FOMO, and never invest money you can’t afford to lose.

Keep your humor cells alive. We laugh, we analyze, we meme.
We sell jokes and opinions — and yes, we bill your sense of humor. 🎪💸
We’re not financial advisors. We’re FUNancial advisors.

Invest at your own risk. Love at any pace. Laugh at every turn. 😄
Be Happy. 😄😄

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