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Walgreens used to be unstoppable. Once a $100 billion drugstore empire, they dominated street corners across America with drive-thrus, clever retail strategy, and a booming pharmacy business model. For decades, they rode the rise of post-war healthcare spending, and Walgreens stock looked like a can’t-miss investment. 👇 SUBSCRIBE for more business breakdowns / @michael-girdley Get my free guide → Why Great Businesses Fail: 10 Multi-Million Dollar Mistakes To Avoid. https://links.girdley.com/10fails-yt ------------------------------------------------------------------ ► For sponsorships or inquiries please reach out to: [email protected] ► Want to get smarter at business? I share a deeper dive into business lessons in my weekly email → https://links.girdley.com/newsletter-yt ► Deep dives on businesses for sale: / @acquisitionsanonymouspodcast ► Follow me on Twitter/X: https://x.com/girdley ------------------------------------------------------------------ But now? The Walgreens collapse is in full swing. Their stock is down 90% from its peak. In 2025 alone, they’re closing 500 stores, and Wall Street’s wondering if they can even survive. In this video, we break down the rise and fall of Walgreens — and compare it directly to smarter competitors like CVS and Amazon PillPack: How Walgreens built a moat around real estate and pharmacy profits Why PBMs (pharmacy benefit managers) broke their pricing power How CVS Caremark and Aetna outmaneuvered them with vertical integration And why tech giants like Amazon are dismantling what's left of the business This isn’t just a failing retail chain story — it’s a dive into missed opportunity, bad leadership, and disruption. 00:00 The rise of Walgreens 01:25 The trends Walgreen's capitalized on 04:11 How PBMs crushed their profits 07:16 CVS makes the smarter move 08:28 Amazon enters the chat 09:23 Walgreens fumbles the turnaround