The Tenderloin Museum to Expand, Bucking Local Trends

In early 2024, the Tenderloin Museum’s plans for the future were thrown into thrilling disarray. Executive Director Katie Conry was getting ready to expand from the ground floor into the basement of the Cadillac Hotel, where the museum currently occupies about 3,200 square feet at the corner of Leavenworth and Eddy.

Kathy Looper, longtime owner of the Cadillac and the museum’s board president, came over with the news. The childcare center next door had closed. Would Conry be interested in taking a look?

“You could see the light bulbs going off in all of our heads as we walked around the space,” Looper remembers. “Much better than a basement.”

Underneath an elegant glass ceiling, they surveyed what had once been the hotel’s formal dining room, built in 1907, and later became Newman’s Gym, where boxers Muhammad Ali, Jack Dempsey, George Foreman and Sugar Ray Robinson all trained or competed. (The floor still shows the boxing ring’s outline.)

At 6,850 square feet, it was so much more space than the museum had ever hoped to gain. And with that space, they could entertain some of their wildest dreams. The opportunity was too good to pass up.

An expansion project would be plenty of work for most museums, especially when so many other San Francisco cultural institutions are struggling with attendance and fundraising. But the Tenderloin Museum is now producing a play, building out an off-site theater venue and launching a capital campaign that seeks to raise $4.2 million over the next three years. The plan is to open the expanded museum in early 2026.

All of this work aims to tell a different, more in-depth story about the Tenderloin — and those who have shaped it.

“For me, it’s all about enhancing people’s understanding of the community,” Looper says. “Instead of the Tenderloin being a negative thing, it could be a positive. We are literally the best cut, the tenderloin of the city.”

Room for a more nuanced history

If Conry has learned one thing during her decade at the museum, it’s that there is so much more to the Tenderloin than the current displays can capture. The museum’s main gallery covers the neighborhood’s vibrant history as an entertainment zone, immigrant hub and center for numerous social movements. On the ceiling, a delightful three-dimensional light-up map shows the Tenderloin’s buildings and intersections.

But in the lobby, just one wall is available for contemporary art shows. Recent history is radically condensed. Space isn’t just an issue for displays, either; staff offices are essentially a closet, making it tricky to have private or sensitive conversations — or solicit donors.

With this expansion, the museum will more than triple in size. The permanent exhibition space will move into the old childcare center, to be replaced by a new neon art gallery, with pieces borrowed from Jim Rizzo’s Neon Works collection.

Two generous galleries behind the permanent exhibition will host contemporary art exhibitions and a long-term installation on South Asian immigrants in the hotel industry. There is also a kitchen, extra bathrooms, a future youth-focused library, and plenty of room to host private events (and hopefully bring in additional revenue).

On a tour through the emptied-out childcare center, which still boasts a diminutive door next to an adult-sized one, the word that kept coming out of my mouth was, “Wow.”

The museum hopes to be closed for only the loudest part of the construction process — just a month or two, this spring. And despite the challenges ahead, Conry is optimistic they can buck local trends, which see San Francisco museums closing either temporarily or permanently. “I think we’re a unique space that has a dedicated following,” she says. “We’re able to be a bit more nimble than the larger organizations.”

That said, she wants the museum to be even more financially stable. Enter, stage left, another income stream: an ambitious play based on the indelible neighborhood story of the Compton’s Cafeteria riot.

Art in service of a larger goal

Five blocks away from the museum, an energetic team of theater professionals is rehearsing lines, blocking fight choreography and turning 835 Larkin St. into a semi-functional 1960s diner.

The play, written by Collette LeGrande, Mark Nassar and Donna Personna, initially premiered at New Village Cafe in 2018 and sold out its two-month-plus run.

Compton’s Cafeteria Riot takes place on an August night in 1966, at a 24-hour diner on the corner of Turk and Taylor. There, fed-up trans women, drag queens and sex workers rebelled in what historian Susan Stryker identifies as the “first known instance of collective militant queer resistance to police harassment in United States history.”

The play, drawn largely from LeGrande and Personna’s own experiences, collapses the distance between audience and performer, lived history and theatrical retelling. Action takes place throughout the diner as audience members sit elbow-to-elbow with actors, or get a plate of pancakes from them.

“This is by far the most ambitious thing I’ve ever done,” says director Ezra Reaves, who has a background in immersive theater. “Every element needs so much more time than a traditional play because we have to build it out in extreme detail.”

In addition to drag, live singing, a violent confrontation and harrowing, real stories, Compton’s Cafeteria Riot comes with the sights, smells and tastes of breakfast (for dinner). The venue’s ongoing transformation from empty concrete box to 1960s diner is remarkable. Set designer Roxy Rose is working on a neon sign for the storefront, and helped source the furnishings — booths, a cash register, bar, stools, jukebox and cigarette machine — that give the space its authentic ambiance.

Reaves says they brought LeGrande and Personna to Amoeba Records to select songs from the time period. “They picked a lot of Lesley Gore, which I love, and we put in a lot of Dionne Warwick,” Reaves says. “So we’ve got plenty of divas in the show.”

It’s been a difficult seven-year journey to bring the play back to audiences, largely due to the pandemic and the team’s commitment to immersive theater, which led to a year of permitting delays. But the importance of the production kept everyone focused on the end goal. “We died on this hill,” Conry says with a laugh.

Compton’s Cafeteria Riot is, Nassar points out proudly, a “trans-centric production.” Conry sees it as an investment in the neighborhood. Reaves echoes the sentiment.

“It’s been my mission to not just make a show for entertainment, but to create a community here,” they say. “To create a piece of art that will continue to bring more people into the fold, and ultimately be an engine of creativity and employment for trans people in the community.”

As national politicians turn trans rights into a wedge issue, Conry says, works of art like Compton’s Cafeteria Riot can bridge divides with understanding and empathy. So much of what the museum does — whether through exhibitions, walking tours, or, now, live theater — is about correcting misconceptions drawn from dominant, damaging narratives.

“There’s so many people who think they’ve never met a trans person, so they don’t know anything about their experience,” Conry says. “The arts really have the ability to change people’s hearts and minds. And when you see the play, you’re really there.”