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© History Oasis
1901-1939
Walgreens founder. Charles Walgreen Sr. was a Swedish immigrant’s son who lost part of a finger in a shoe factory. After the shocking incident, he pivoted to a pharmacy career. When he decided to start his own pharmacy, he threw his last three cents in the Chicago River for luck. In his first Walgreens, he invented the milkshake with the help of an employee. Walgreen Sr. built the pharmacy chain from one store to 490 stores across 37 states.
1939-Early 1950s
Chuck, as he liked to be called, was the founder’s son. He started his career as a drug apprentice for his dad at 19. He expanded the chain internationally into Mexico and Puerto Rico. Purchased the Sanborns department store chain in Mexico in 1946. And grew sales to $141 million with 17,500 employees by the time he stepped down.
Early 1950s-1998
Cork started as a stock boy at the company in 1952, before taking the reins of Walgreens when his father retired. He’s best known for pioneering drive-thru pharmacies and the “Main & Main” corner strategy. Cork also owned Wag’s restaurant chain in the 1980s. With Cork at the top, Walgreens saw 23 consecutive years of record growth. Where the pharmacy expanded from 561 stores ($817M sales) to 2,400 stores ($13B sales). He would be the last family member to lead the company.
1998-2002
Daniel Jorndt was the first non-family CEO. Jornt was a former pharmacist who maintained the company’s growth streak. He updated the tech stack for the future. Let’s just say he made Walgreens into the modern pharmacy that we all know today.
2002-2006
Starting as a pharmacy intern in 1966, David Bernauer created the Intercom Plus system, processing millions of daily transactions. Implemented Basic Department Management for automated inventory. Achieved 30th consecutive year of record profits. Bernauer was known for his quiet, methodical leadership style. Something that modern leaders could take notes from (we are talking about you, Elon).
2006-2008
Jeff Rein took the reins of Walgreens briefly (no pun intended). He expanded Walgreens’ reach by acquiring the Take Care Health Systems clinic chain in 2007. Known for a decisive, concise management style. But he fell from grace in the ’08 financial crisis.
2008-2009
Alan McNally was the acting CEO during the financial crisis. He was just an interim CEO for Walgreens until the board could find a new CEO.
2009-2014
The global expansion architect. Greg Wasson started as a pharmacy intern in 1980 and moved up the corporate ladder. He acquired Duane Reade ($1.075B) and Drugstore.com ($409M). He also made a $6.7B Alliance Boots deal. Wasson was notorious for his Express Scripts battle with the Al Sharpton coalition involvement. He was on the other side of the law when the SEC fined him $160,000 for misleading investors in 2018.
2015-2021
Steffano Pessina was an Italian billionaire dealmaker and trained nuclear engineer. He built Alliance Boots from one distributor into a $40B empire. Pessina bought Walgreens with its own money through a complex merger. He described himself as a “company builder,” not a retailer.
2021-2023
Known as the barrier-breaking executive. Rosalind Brewer was a former Starbucks COO and Sam’s Club CEO. She was the first Black woman to lead a Fortune 500 company. She led Walgreens during the COVID recovery period. Brewer stepped down unexpectedly for reasons unknown.
2023-2025
Turnaround specialist Tim Wentworth was a former Cigna executive who came out of retirement. He inherited a $1B cost-cutting plan and a 48% dividend slash. Tim closed VillageMD clinics and reduced store hours. He ended Walgreens’ public era when Sycamore Partners acquired the company for $10B.
2025-Present
Walgreens’ private equity era begins with Mike Motz. Motz is a former Staples US Retail CEO and Shoppers Drug Mart President. He was recently named CEO on August 28, 2025, the same day Sycamore Partners completed its acquisition. Motz will be tasked with refocusing on core pharmacy/retail after its failed healthcare expansion.
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