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

Trendingnow

1

MacKenzie Scott, Melinda French Gates, and Lauren Sánchez Bezos are rewriting the rules of billionaire giving—one quietly, one strategically, one very publicly

2

After donating $48 billion to the Gates Foundation, Warren Buffett is quietly ending one of the biggest philanthropic relationships in history

3

Current price of silver as of Tuesday, July 14, 2026

1

MacKenzie Scott, Melinda French Gates, and Lauren Sánchez Bezos are rewriting the rules of billionaire giving—one quietly, one strategically, one very publicly

2

After donating $48 billion to the Gates Foundation, Warren Buffett is quietly ending one of the biggest philanthropic relationships in history

3

Current price of silver as of Tuesday, July 14, 2026
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
Add Fortune on Google for similar content.

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
Add Fortune on Google for similar content.

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
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • 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
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Newsletters

A headshot of Dave Bozeman, CEO of C.H. Robinson.
NewslettersEye on AI
The secrets of an unheralded AI success story
By Jeremy KahnJuly 14, 2026
8 hours ago
MacKenzie Scott, Melinda French Gates, and Lauren Sánchez Bezos are rewriting the rules of billionaire giving—one quietly, one strategically, one very publicly
NewslettersMPW Daily
MacKenzie Scott, Melinda French Gates, and Lauren Sánchez Bezos are rewriting the rules of billionaire giving—one quietly, one strategically, one very publicly
By Sydney LakeJuly 14, 2026
10 hours ago
Why is a satellite like a race car? Apex and Toyota’s racing division have an answer
NewslettersTerm Sheet
Why is a satellite like a race car? Apex and Toyota’s racing division have an answer
By Allie GarfinkleJuly 14, 2026
16 hours ago
Group of business people waiting in line for job interview in modern office. (Photo: VioletaStoimenova/Getty Images)
NewslettersFortune Tech
Almost 200 economists warn of AI-driven job displacement
By Andrew NuscaJuly 14, 2026
17 hours ago
Bahrain EDB bids to win investors despite mounting headwinds 
NewslettersFortune Gulf Brief
Bahrain EDB bids to win investors despite mounting headwinds 
By Melissa HancockJuly 14, 2026
17 hours ago
MassMutual CEO says Americans’ share of the U.S. debt is going up $10 a day
NewslettersCEO Daily
MassMutual CEO says Americans’ share of the U.S. debt is going up $10 a day
By Diane BradyJuly 14, 2026
18 hours ago

Most Popular

MacKenzie Scott, Melinda French Gates, and Lauren Sánchez Bezos are rewriting the rules of billionaire giving—one quietly, one strategically, one very publicly
Newsletters
MacKenzie Scott, Melinda French Gates, and Lauren Sánchez Bezos are rewriting the rules of billionaire giving—one quietly, one strategically, one very publicly
By Sydney LakeJuly 14, 2026
10 hours ago
After donating $48 billion to the Gates Foundation, Warren Buffett is quietly ending one of the biggest philanthropic relationships in history
North America
After donating $48 billion to the Gates Foundation, Warren Buffett is quietly ending one of the biggest philanthropic relationships in history
By Marco Quiroz-GutierrezJuly 14, 2026
9 hours ago
Current price of silver as of Tuesday, July 14, 2026
Personal Finance
Current price of silver as of Tuesday, July 14, 2026
By Joseph HostetlerJuly 14, 2026
17 hours ago
United States' $39 trillion national debt will mean fewer jobs at lower wages for Gen Z, according to think tank
Economy
United States' $39 trillion national debt will mean fewer jobs at lower wages for Gen Z, according to think tank
By Eleanor PringleJuly 14, 2026
16 hours ago
The U.S. spent $30 billion to ditch textbooks for laptops and tablets: The result is the first generation less cognitively capable than their parents
Innovation
The U.S. spent $30 billion to ditch textbooks for laptops and tablets: The result is the first generation less cognitively capable than their parents
By Sasha RogelbergJuly 12, 2026
3 days ago
Current price of gold as of July 14, 2026
Personal Finance
Current price of gold as of July 14, 2026
By Danny BakstJuly 14, 2026
14 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.