The rise and fall of Walgreens: from $100B to bankruptcy watch

A $100B pharmacy empire that rode two perfect waves for decades — now worth less than it was 30 years ago.

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By The Numbers

8,700

locations at peak

-90%

stock crash from peak

<$10B

current market value

What They Nailed Early

Rode two massive tailwinds: car-centric America and exploding healthcare spend. Paid up for corner real estate with drive-thrus. Pharmacy in the back forced customers past high-margin impulse buys — brilliant flywheel.

What Changed

Pharmacy benefit managers (PBMs) inserted themselves between Walgreens and profits. When Walgreens tried to fight Express Scripts in 2012, they lost 20-30% of revenue overnight and capitulated. CVS vertically integrated by buying a PBM and insurer Aetna. Walgreens stayed a dumb box while Amazon entered with home delivery.

Where it Landed

Stock down 90%, worth what it was 30 years ago. Closing 500 stores in 2025 alone. Third or fourth CEO attempting turnaround. The decisions that killed them were made years ago when they missed the window.

The Principles

Vertical integration or die. When middlemen control your pricing, you're a commodity with no leverage against the squeeze.

Technology doesn't care about your real estate moat. Amazon's delivery model made billions in corner locations irrelevant overnight.

Missing the strategic window is terminal. You can't fix in year 10 what you should have done in year 3.

Builder's Takeaway

If you're in a consolidating industry, remember:

•

When PBMs or middlemen emerge, integrate or get crushed on margins

•

Real estate moats evaporate when tech enables delivery to the home

•

Strategic windows close fast — thrashing later won't fix missed bets

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