The mid-to-late twentieth century in the United States was defined by deep counter-cultural shifts, intense political polarization, and a heavy restructuring of the nation’s domestic drug policies. Within this turbulent landscape, the life of Wesley A. Pomeroy stands as an extraordinary study in progressive law enforcement. Born on January 1, 1920, in Burbank, California, Pomeroy navigated an eclectic career path that seamlessly bridged traditional law enforcement, radical counter-culture event management, and federal drug policy reform. His professional history—stretching from the chaotic muddy fields of the 1969 Woodstock Music and Art Fair to the boardrooms of the National Organization for the Reform of Marijuana Laws (NORML) and the upper echelons of the Drug Enforcement Administration (DEA)—fundamentally challenged standard assumptions regarding the intersection of police work and civil liberties. [1, 2, 3]
The Crucible of Progressive Law Enforcement
Pomeroy began his adult life in uniform, serving as an officer with the California Highway Patrol before enlisting in the United States Marine Corps to see direct combat in the Pacific theatre during World War II, including the Battle of Okinawa. Following his military service, he returned to California law enforcement, climbing the ranks to become the undersheriff of San Mateo County while simultaneously earning a law degree from the San Francisco Law School. Unlike many of his contemporary peers during the Cold War era, Pomeroy developed a highly progressive, non-combative philosophy toward public crowd control. He asserted that civil protesters and mass assemblies should be engaged through strategic communication and institutional cooperation rather than structural threats, riot batons, and brute force. [4, 5, 6, 7, 8]
He proved the efficacy of his peaceful de-escalation strategies during the contentious 1964 Republican National Convention in San Francisco, where his security teams successfully managed aggressive political demonstrations without triggering mass violence. This success caught national political attention. In 1968, U.S. Attorney General Ramsey Clark appointed Pomeroy as a special assistant to coordinate federal anti-crime initiatives, placing him in the command post for the 1968 Democratic National Convention in Chicago. Though Chicago Mayor Richard Daley ultimately rejected Pomeroy’s de-escalation strategies in favor of a violent police crackdown against anti-war demonstrators, Pomeroy emerged from the federal government with a bulletproof reputation as a calm, highly capable coordinator who viewed citizens—even those using illicit substances or protesting the state—with inherent dignity. [2, 9, 10, 11, 12]
The Peacekeeper of Bethel: The Woodstock Logistics
In early 1969, as the organizers of Woodstock Ventures scrambled to plan an unprecedented, three-day outdoor musical festival in Bethel, New York, they faced a massive logistical crisis. Local municipalities were terrified that hundreds of thousands of anti-war, drug-using youth would descend on their rural towns, and standard security firms refused to touch the event. Seeking a leader who could maintain structural order without inciting a riot, the festival organizers hired the 49-year-old Pomeroy to serve as their Vice President and Director of Security. [13]
Pomeroy’s leadership at Woodstock became legendary. Facing an overwhelming, unexpected influx of nearly 500,000 attendees alongside a total breakdown of local food, traffic, and sanitation infrastructure, New York Governor Nelson Rockefeller threatened to deploy the National Guard to forcibly clear the site. Pomeroy fiercely resisted military intervention. He banned his security personnel from carrying firearms, strictly instructed them never to make low-level drug arrests, and organized the famous “Please Force”—a security unit tasked entirely with helping attendees find water, medical aid, and shelter. By treating the massive crowd as a community of citizens rather than an unruly mob of criminals, Pomeroy single-handed prevented a humanitarian disaster, ensuring that Woodstock became a global symbol of peaceful counter-cultural assembly. [14, 15]
The Federal Paradox: Outlawing and Overseeing the Drug War
Following his success at Woodstock and a stint in high-profile security roles, including leading the security for Led Zeppelin’s 1973 US tour, Pomeroy became Chief of Police for Berkeley, California, in 1974. His progressive views continued to evolve, and he became a vocal advocate for the total decriminalization of marijuana, joining the board of directors for the National Organization for the Reform of Marijuana Laws (NORML). [14, 16]
In a unique turn of events, in 1977, Pomeroy was appointed as the Assistant Director of the Drug Enforcement Administration (DEA) under the Carter administration. This move created a paradox where a proponent of cannabis reform, and a sitting NORML board member, was helping lead a major federal drug enforcement agency. Pomeroy aimed to steer federal efforts away from low-level user harassment and toward targeting violent traffickers. He remained a firm believer in progressive law enforcement and community-based policing until his death on May 4, 1998. [5, 14]
Factual Bibliography
- Obituaries and Mainstream Press Archives:
- The New York Times. “Wesley A. Pomeroy, 78, Security Chief at Woodstock Festival.” Written by Robert McG. Thomas Jr., published May 15, 1998. The New York Times Digital TimesMachine.
- National Drug Strategy Network (NDSN). “Wesley Pomeroy, Police Officer and Drug Policy Reformer, Dies at Age 78.” Published May/June 1998 Edition. NDSN NetNews Archive Portal. [5, 14, 15, 17, 18]
- The Woodstock & Security Logbooks:
- Woodstock Whisperer Historical Project. “Woodstock Wes Pomeroy: The Philosophy of the Please Force.” Editorial Series, published January 1, 2016. Woodstock Whisperer Digital Archive.
- Pomeroy, Wesley A. “The Management of Mass Assemblies and Counter-Culture Security Realities.” Interview transcript preserved via the Redwood City Tribune Public Library Collection. [15, 19]
- Drug Policy Reform and NORML Histories:
- Stroup, Keith. High in America: The True Story Behind NORML and the Politics of Marijuana. New York: Viking Press, 1981. [Digital Monograph Access via CannaLib Archive Collection].
- The Drug Enforcement Administration Museum. “The Carter Administration Structural Matrix: Assistant Directors and Policy Pivots (1977–1881 Records).” Arlington, VA: DEA Historical Office. [16]
If you want to keep tracking this law enforcement timeline, let me know if you would like me to locate:
- The exact protocols he wrote for the 1969 Woodstock “Please Force”
- The clippings and internal debate records regarding his dual role at NORML and the DEA
- The genealogical links tracking Wesley back to his California Highway Patrol roots
[5] https://ndsn.org
[6] https://woodstockwhisperer.info
[12] https://woodstockwhisperer.info
[13] https://woodstockwhisperer.info
[16] https://cannalib.eu
August 17, 2026 at 2:30 pm
As a Woodstock alum and someone who has led tours in the Museum at Bethel Woods Center for the Arts (on the site of Woodstock 1969), this is a wonderfully informative article. Wes Pomeroy is sadly an unsung hero of Woodstock’s fame for being four days of peace, love, sharing, and understanding. Hugh Romney (later Wavy Gravy) is more often mentioned (and deservedly so), but Pomeroy was the person who created the space for Romney’s approach of a “Please Force.”
Thank you.