• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
NewslettersFortune Archives

Fortune Archives: The roots of Walgreens’ woes

Phil Wahba
By
Phil Wahba
Phil Wahba
Senior Writer
Down Arrow Button Icon
Phil Wahba
By
Phil Wahba
Phil Wahba
Senior Writer
Down Arrow Button Icon
June 29, 2025, 7:00 AM ET
Photograph by The Voorhes for Fortune

In early 2016, U.S. druggist Walgreens had recently bought Britain’s popular Boots Alliance chain to create the first international drugstore empire. The acquisition was the brainchild of Italian billionaire and dealmaker extraordinaire Stefano Pessina, and a deep dive by Fortune asked “Can a brilliant dealmaker become a killer retailer?”

Recommended Video

Almost a decade later, we have an answer: a resounding “no.” As detailed in my recent Fortune feature, Walgreens has stumbled mightily in the last decade. Its value on the stock market was $100 billion in 2015, but by the time Walgreens Boots Alliance struck a deal to be bought by a private equity firm, Sycamore Partners, and go private after 98 years on the stock market, the company’s market cap had fallen 90%, to $10 billion.

Pessina, who will remain a major shareholder after the take-private deal, was better known for his dealmaking prowess than his skill at running stores. “I am not a retailer,” he admitted to Fortune’s Jennifer Reingold in 2015.

Ignoring retail in favor of deals has turned out to be a big factor in Walgreens’ decline. Under Walgreens’ business model, the front-of-store general-merchandise sales and its prescription business feed off each other. But over time, Walgreens, which is now closing some 1,200 stores out of 8,700, has let its stores deteriorate and became an e-commerce laggard. It hasn’t helped that Walgreens, like many large pharmacies, has locked up much of its store inventory to ward off shoplifters—a move that ended up warding off many shoppers too.

Meanwhile Pessina, who bragged in 2015 of having done 1,500 M&A deals in his life, kept making deals. With his eye on competitor CVS, he made a bid for Rite Aid, the distant No. 3 in the U.S. drugstore wars, and its 5,000 stores—an expensive adventure that later led to the closing of many of the 2,000 Rite Aid stores that regulators allowed it to buy. Other deals followed as Walgreens sought to mimic CVS’s focus on health care clinics, but many of those acquisitions have been unwound since, at a loss of billions to Walgreens.

A re-read of the 2016 Fortune piece underlines the lack of progress on key problems analysts were concerned about. Back then, Wall Street worried about Walgreens being pinched by tightening reimbursement rates for the drugs it dispenses and the fact that, unlike CVS with its Caremark, Walgreens didn’t own a pharmacy benefits manager to exert more influence on drug companies. Walgreens is still feeling the reimbursement pinch and still has no PMB of its own. And in 2015, there were also worries about Walgreens’ enormous debt load from its Boots acquisition, which stoked fears it had too little room for error as it attempted to turn around. Analysts are expressing exactly the same fears today.

This is the web version of the Fortune Archives newsletter, which unearths the Fortune stories that have had a lasting impact on business and culture between 1930 and today. Subscribe to receive it for free in your inbox every Sunday morning.
About the Author
Phil Wahba
By Phil WahbaSenior Writer
LinkedIn iconTwitter icon

Phil Wahba is a senior writer at Fortune primarily focused on leadership coverage, with a prior focus on retail.

See full bioRight Arrow Button Icon

Latest in Newsletters

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Most Popular

placeholder alt text
C-Suite
OpenAI’s Sam Altman says his highly disciplined daily routine has ‘fallen to crap’—and now unwinds on weekends at a ranch with no cell phone service
By Jacqueline MunisFebruary 5, 2026
2 days ago
placeholder alt text
Politics
Meet the Palm Beach billionaire who paid $2 million for a private White House visit with Trump
By Tristan BoveFebruary 3, 2026
4 days ago
placeholder alt text
Travel & Leisure
How Japan replaced France as the country young Americans obsessively romanticize—they’re longing for civility they don’t see at home
By Nick LichtenbergFebruary 5, 2026
2 days ago
placeholder alt text
Success
After decades in the music industry, Pharrell Williams admits he never stops working: ‘If you do what you love everyday, you’ll get paid for free'
By Emma BurleighFebruary 3, 2026
4 days ago
placeholder alt text
Investing
Ray Dalio warns the world is ‘on the brink’ of a capital war of weaponizing money—and gold is the best way for people to protect themselves
By Sasha RogelbergFebruary 4, 2026
2 days ago
placeholder alt text
Crypto
Bitcoin whales and ETFs are baling out of the market; UBS warns: ‘Crypto is not an asset’
By Jim EdwardsFebruary 6, 2026
17 hours ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.


Latest in Newsletters

NewslettersMPW Daily
Inside the Kansas City Chiefs’ strategy to attract female fans—and what the rest of the NFL can learn ahead of the Super Bowl
By Emma HinchliffeFebruary 6, 2026
13 hours ago
Woman with blonde hair sitting on stage
Newsletterssuccess
Skier Lindsey Vonn is competing in the 2026 Winter Olympics despite a ruptured ACL: She says grit is the most important quality in life and business
By Emma HinchliffeFebruary 6, 2026
13 hours ago
NewslettersCFO Daily
How e.l.f. Beauty has used Super Bowl ads to rocket from 10% brand awareness to 40%
By Sheryl EstradaFebruary 6, 2026
16 hours ago
Image of Moltbook app logo on a smart phone with another image of the Moltbook logo in the background.
NewslettersTerm Sheet
Moltbook is the talk of Silicon Valley. But the furor is eerily reminiscent of a 2017 Facebook research experiment
By Allie GarfinkleFebruary 6, 2026
17 hours ago
NewslettersFortune Tech
Gemini takes a bite out of ChatGPT share
By Alexei OreskovicFebruary 6, 2026
17 hours ago
NewslettersCEO Daily
Disney’s Bob Iger achieves an essential feat for outgoing CEOs: giving his successor a clean slate
By Diane BradyFebruary 6, 2026
18 hours ago