BOOK REVIEW: A People’s History of SF’s Most Notorious Neighborhood

The Tenderloin: Sex, Crime, and Resistance in the Heart of San Francisco by Randy Shaw, Urban Reality Press, 2025

"Any city that doesn't have a Tenderloin isn't a city at all."
—Herb Caen, longtime San Francisco Chronicle columnist 

Few San Francisco neighborhoods have had more ups and downs than the 33-block area still called “The Tenderloin”—a name that derives from the late 19th century police practice of shaking down local restaurants and butcher shops by taking their best cuts of beef in lieu of cash bribes.

At various periods in its storied past, the Tenderloin has been home to famous brothels, Prohibition-era speakeasies, San Francisco’s first gay bars, well-known hotels and jazz clubs, film companies and recording studios, and professional boxing gyms. 

In 1966, trans people hanging out at the all-night Compton’s Cafeteria staged a militant protest against police harassment three years before the more famous LGBTQ uprising at the Stonewall Inn in NYC. During the last decade, the Tenderloin has become better known for its controversial side-walk camping, open-air drug markets, and fentanyl abuse.

The failure of municipal government to deal with those social problems— in a residential neighborhood for working-class families with 3,000 children—contributed to recent electoral defeats of a district attorney, city supervisor, and San Francisco’s second female and African-American mayor.

For the past 45 years, Randy Shaw has been a fixture of the place as co-founder of its Tenderloin Housing Clinic (THC). After graduating from law school nearby, Shaw became involved in fights for tenants’ rights and more affordable housing at a time when blue collar neighborhoods in San Francisco were starting to gentrify.

A Unionized Non-Profit

The THC, which now employs 200 SEIU Local 1021-represented staff members, began to acquire and develop its own network of Single Room Occupancy (SRO) buildings in the Tenderloin, as an alternative to run-down private landlord-owned ones. 

Today, THC provides subsidized housing and wrap-around services to several thousand of the city’s most needy tenants—who might otherwise be among the social outcasts living in the surrounding streets. Shaw estimates that the Tenderloin has a higher percentage of housing in nonprofit hands than any central city neighborhood in the nation, an arrangement that safeguards its distinctive character as an economically mixed neighborhood with many low-income people among its 20,000 residents.  

In this second edition to his book, The Tenderloin: Sex, Crime and Resistance in the Heart of San Francisco, Shaw recounts how this multi-racial working-class enclave managed to survive, if not always thrive, amid a city dominated by tech industry wealth and privilege. 

That history of neighborhood resistance to displacement is also on display at the Tenderloin Museum (TLM). Created ten years ago, with much help from the author, this venue for community-based, historically-inspired cultural programming now operates under the direction of Katie Conry. 

In her Forward to Shaw’s book, Conry describes the TLM’s many art shows, special exhibits, theatre productions, walking tours, and other public programs that have drawn 50,000 people to a downtown area many out-of-town visitors (and locals) are told to avoid. On April 11, for example, the THC is hosting a new production of The Compton’s Cafeteria Riot to commemorate that “collective act of resistance” and “the on-going fight for transgender rights.” (For ticket info, see: https://www.tenderloinmuseum.org/the-comptons-cafeteria-riot-play)

Community Benefits Agreements

DSA chapters fighting gentrification—or trying to make sure its benefits are more equitably shared—will find Shaw’s book to be an invaluable guide to effective activism around housing issues. It illustrates how persistent and creative grassroots organizing can challenge and change urban re-development schemes designed for the few, rather than the many. In too many California cities, it’s the latter who continue to get pushed out and left behind in the name of “neighborhood improvement.”

A central case study in The Tenderloin is the author’s account of how community residents won a pioneering “community benefits agreement” (CBA) with three powerful hotel chains. In the early 1980s, Hilton, Holiday Inn, and Ramada wanted to build three luxury tourist hotels adjacent to the Tenderloin. Given the city’s pro-development political climate at the time, these hospitality industry giants expected little organized opposition to their plans. Then Mayor Diane Feinstein lauded them for “bringing a renaissance to the area.”

However, as originally unveiled, their blueprint would have transformed nearby residential blocks by “driving up property values, leading to further development, and, ultimately the Tenderloin’s destruction as a low-income residential neighborhood.”

An Organizing Case Study

Among those faced with the prospect of big rent increases and eventual evictions were many senior citizens, recently arrived Asian immigrants, and longtime residents of SRO buildings in dire need of better ownership and management. Fortunately, this low-income, multi-racial population included some residents with “previously unrecognized activist and leadership skills” that were put to good use by campaign organizers, like Shaw, who were assisting their struggle. 

During a year-long fight, hundreds of people mobilized to pressure the city Planning Commission to modify the hoteliers’ plans. As Shaw reports, the resulting deal with City Hall created “a national precedent for cities requiring private developers to provide community benefits as a condition of approving their projects.”

Each of the hotels contributed $320,000 per hotel per year for twenty years for low-cost housing development. They also had to sponsor a $4 million federal Urban Development Action Grant (UDAG) for the acquisition and renovation of four low-cost Tenderloin SROs. In addition, each hotel had to pay $200,000 for community service projects, and give priority in employment to Tenderloin residents. 

Four decades later, community benefits agreements of this sort are not so unusual. But, in the absence of major new federal investment in public housing built with union labor, they are still much needed.  

Where tax breaks or rezoning encourages various forms of private development today, the only way to win additional low-income housing units, living wage jobs, local hiring, or preservation of open space for public use is through grassroots campaigning by community-labor coalitions, aided by sympathetic public officials. 

Otherwise mayors and city councils under the thumb of developers will simply offer financial incentives with few strings attached—whether the project involved is a new hotel, casino, shopping center, office building, or luxury apartment building.

Organizers’ optimism

Back in the Tenderloin, as Shaw reports in the conclusion to his book, residents in recent years have had to mobilize around basic public safety issues.  Pandemic driven economic distress flooded their neighborhood with tent dwellers, drug dealing, and street crime that added to small business closures, drove tourists away, and made daily life hazardous for longtime residents (except when state and local politicians cleaned things up for high-profile gatherings like the Asia-Pacific Economic Cooperation leadership meeting in S.F. two years ago).

Nevertheless, the author ends on an optimistic note (characteristic of organizers): “New restaurants and small businesses are again opening in the Tenderloin. Street and crosswalk changes make the neighborhood among the city’s most walkable. New housing has increased the Tenderloin’s population…” 

But, Shaw reminds us, residents of this urban enclave must still fight to achieve “the quality of life common to other San Francisco neighborhoods,” while “protecting an ethnically diverse, low-income, and working-class community” with a storied past and always uncertain future.