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The Downtown San Francisco I Loved Was a Holiday Wonderland

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A young man and woman pose for a photo inside a clothing store while holding a oversized Timberland work boot.
A young Rocky Rivera (right) poses with her beloved wheat color Timberland boot. She worked in the downtown San Francisco Timberland store in the early 2000s. (Courtesy of Rocky Rivera)

Frisco Foodies is a recurring column in which a San Francisco local shares food memories of growing up in a now rapidly changing city.


his holiday season, my teenage son asked for his first pair of classic wheat Timberland boots. Favored by construction workers and rap legends, Timberlands are prized for their lifelong durability and rugged aesthetic. I should know — I’ve had my own pair of wheats on ice for over twenty years. The style of shoe is canon in hip-hop history; when I interviewed the Wu-Tang Clan for The Source in 2007, they mentioned that their performance fee back then, split between the nine original members, was sometimes only enough for a pair of Timbs.

In the early 2000s, when I worked as a retail associate at Timberland’s downtown San Francisco store, I learned that only the classics were resoleable for life, and that they were water-resistant enough to withstand a quick downpour but not a heavy deluge. They were a good investment, I told my son, but please let Mom pick them out. I wanted him to have a lasting pair.

I loved that downtown Timberland job and have fond memories of taking the J-Church train from Mission Terrace over Dolores Park and through the Castro, before it finally dropped me off at Market & Powell. I was convinced it was the most beautiful Muni line in the city, and the holiday season, with the Embarcadero skyline lit up, made the trip even more festive. It was just close enough to Union Square to feel the holiday cheer in the crisp winter air and hear a melancholy Coltrane song from a street performer’s saxophone. The store itself was small enough for me to form lasting relationships there. And the employee discount was good enough to allow me to play Santa during the holidays.

Over a box a Timberland boots, a hand holds up an engraved leather name tag that reads "Krishtine"
A relic of the downtown San Francisco of the early 2000s. (Courtesy of Rocky Rivera)

Fast forward to 2023 and I haven’t stepped foot in downtown for years — not since the pandemic accelerated the neighborhood’s retail apocalypse. What used to be the prime destination for Christmas shopping now has to contend with two-day Amazon Prime shipping and a barrage of Fox News reports about the whole area being an open-air drug market. Cop cars park on the corner next to Louis Vuitton, hoping to deter roving gangs of juvenile shoplifters known for their chaotic smash-and-grabs. Even a high-end supermarket couldn’t save its customers from “machete-wielding” assailants and drug users overdosing in the bathroom — though locals might wonder who Whole Foods was trying to cater to downtown in the first place.


The neighborhood’s food scene isn’t doing much better. Chefs lament about how the lack of foot traffic and downtown office workers has shut down both trendy power-lunch spots (Barbacco) and beloved family-run staples (Turtle Tower). The nearby San Francisco Shopping Centre Mall is a shell of itself — about 45 percent empty after the Nordstrom closed over the summer. Even during the lunch rush, the food court often feels deserted.

The downtown I remember had shoplifters, drug users, scammers and weirdos, too — that part hasn’t changed as much as today’s news headlines might lead you to believe. But back when I worked downtown, I could spend my half-hour lunch breaks on a $2.50 slice combo at Blondie’s Pizza or splurge on a $15 roast chicken with mashed potatoes at Wolfgang Puck’s bistro in the Macy’s Cellar. Sometimes I’d have clam chowder in a sourdough bowl at Boudin; other days, I would save my pennies and meet my family for a celebratory dinner at Tad’s Steakhouse. When I was really broke, there was always the McDonald’s on Powell, where the old Filipino manongs used to hang out and watch the tourists on cable cars go past — not to mention the countless corner stores that sold bagels, coffee and sandwiches next to the Swisher Sweet cigars I used to wrap my blunts.

Most of these places are gone or relocated from where they originally stood. Even the McDonald’s are shutting down. And the Timberland store I loved so much? That’s gone as well. My engraved leather name tag and pristine-condition wheats are all that remain of that era of downtown San Francisco.

‘Make the City Better’

“No one remembers, right before the pandemic, how many restaurants were closing, how many chefs burned out, how bad business was, how bad the rent was,” says Christian Ciscle, a chef and longtime San Francisco resident who owns SF Chickenbox — a restaurant known for its perfectly golden-fried chicken, homemade hot sauces and chewy-pillowy mochi muffins. I’ve followed Ciscle’s seasoned breadcrumb trail from Little Skillet, where he served chicken and waffles to clubgoers at 330 Ritch, to Wing Wings in Lower Haight and now his new location in North Beach.

A person in a baseball cap stands in the doorway of a city building.
Christian Ciscle stands outside of the 332 Pine St. location of his latest project, Sucka Flea, a pop-up flea and swap market. (Aryk Copley for KQED)

Ciscle believes the mental health crisis and crime that have always existed in San Francisco are now compounded by the constant barrage of videos that serve as fuel for conservative media outlets looking to blame progressive politicians. Experiencing even one incident first-hand is enough to make a liberal store owner switch ideologies to welcome increased police presence — an approach Ciscle believes doesn’t actually deter property crime but instead targets the most vulnerable. “There’s truth to how bad it is, but unhoused people didn’t make [downtown] bad,” he says. “What made them unhoused did.”

Downtown San Francisco has never been an ideal place for a food business, in Ciscle’s opinion: “It was always dead after 5 p.m. on weekdays and weekends. It was never a place to do business, unless you’re Tyler Florence.” And when the pandemic hit and business came to a screeching halt, he saw how vulnerable everyone was to closing down. “Nobody was bulletproof,” he says. “Everyone had to reassess their business model, their values.”

A group of people stand stand outside of a city building.
Vendors take a break outside of 332 Pine St. from the Sucka Flea market in San Francisco, Calif. on Nov. 5, 2023. (Aryk Copley for KQED)

Luckily, a newly created nonprofit called SF New Deal supported food businesses by paying them to provide meals for various community orgs. It paid SF Chickenbox for 200 meals a day — a source of money Ciscle could rely on in unsteady times, enabling him to keep his business open. Earlier this year, the program evolved into Vacant to Vibrant (V2V), a new initiative that tries to activate empty office spaces to accommodate small business pop-ups.

Ciscle didn’t want to expand SF Chickenbox into downtown. But his experience throwing community festivals in years past made him perk up at the prospect of doing more than just food. The V2V program would allow him to utilize his long-standing relationships with vendors, artists, DJs and local artisans. So Ciscle created Sucka Flea, a pop-up flea market (and homage to San Francisco’s “Sucka Free” alias) that would also include local food vendors like Hyphy Iceez and Tasty Tings. The flea market’s last event of the year — a holiday-themed market — will take place at Hub Embarcadero (Howard St. and Embarcadero) on Saturday, Dec. 16.

For jewelry designer Chelsea Macalino-Calalay, Sucka Flea has provided a consistent space to sell her wares. At the Pine Street pop-up, her colorful baubles catch the eye of my five-year-old daughter, who otherwise would have no business in the Financial District on a Sunday afternoon. Macalino-Calalay is one of the thousands of Filipino Americans who were displaced from SoMa’s Manilatown enclave that once spanned ten city blocks to the International Hotel on Kearny Street. Macalino-Calalay’s family emigrated in the late ’60s and early ’70s. Her grandfather’s siblings were first employed as sign-painters at the Thomas Swan Sign Company when it was on Howard Street, then as food and service industry workers.

A smiling vendor greets a customer at an indoor flea market.
The author chats with vendors Chelsea Macalino-Calalay (center) and Dante Kaleo during the November edition of Sucka Flea’s downtown pop-up. (Aryk Copley for KQED)

“I used to be a crepe chef and a cake decorator and a hostess and a waitress. So I worked in food, too. It showed me a lot about work ethic as well as perseverance,” she recalls with pride. “But it also showed me what I don’t want in a work environment.”

Macalino-Calalay remembers downtown San Francisco as the place her family squeezed into on weekends, patronizing the fresh Filipino food at Aling Mary’s Unimart, relishing her lola’s home cooking, and enjoying meals from the McDonald’s on Bryant, where her father worked as a manager with an all-Filipino staff. Community orgs like West Bay, Soma Pilipinas and United Playaz helped her as a young girl, and Macalino-Calalay is seeing a resurgence of these kinds of resources that she hopes will continue.

When asked if things are better or worse today, she pauses. “From someone who didn’t grow up in SF, ‘worse’ is very subjective. Things being worse just looks like us not being there,” she says about her family of SF locals, who are now scattered throughout the East Bay and Outer Mission. Some are still in the SoMa, where her jewelry is now being shown in a special exhibit at SFMOMA with artist Pacita Abad. It’s a full-circle moment for a Frisco girl, who used to see parts of the museum being painted below the front steps of her family home on Langton Street.

A person poses for a photo holding up a bowl of food in an indoor setting.
Tanya Herrera (left) and Catherine Pham enjoy taking photos with some vintage collectibles. (Aryk Copley for KQED)

Meanwhile, Whack Donuts owner Vandor Hill, a born-and-raised San Franciscan, opened his own temporary pop-up shop through the V2V program. who sells delectable-looking peach cobbler doughnuts and Donkey Kong bread doughnuts, alongside trendy flavors like Thai tea and horchata. While he has appreciated the opportunity, He believes first-time business owners in San Francisco need even more support from City Hall — and actual follow-through from local politicians. “Like the Bobby Byrd song, ‘Saying It and Doing It Are Two Different Things.’ The mayor along with the Board of Supervisors have been saying a lot in terms of enforcing law and the homeless situation, but have yet to really make any lasting moves for improving these topics,” he says.

Ciscle, for his part, believes pandemic-era programs like SF New Deal and Vacant to Vibrant are proof that money is out there for local food business owners: “There’s billionaires blocks away from us right now that could literally fund some shit and make it better — not that they should be running the city,” he says. “There’s money to fund programs out there, not just locking people up. To feed people, put people in houses. Make the city better.”

“People are more concerned with seeing [the unhoused] on the street,” Ciscle says. “They’re gonna put a planter on the sidewalk there so they can’t sleep and then be mad it gets knocked over or graffiti-ed up. And now we have two problems.”

A person with long hair laughs while sitting at a table talking to someone else.
Nina Parks gives the author a tarot card reading. (Aryk Copley for KQED)

For now, Sucka Flea is occupying some of these empty spaces and providing small business owners with shared foot traffic and community. It can’t fix all of the problems facing downtown San Francisco, but it’s a start. After all, creating a family-friendly space that attracts folks from all over the Bay Area to shop downtown is no small feat — and spending holiday shopping dollars with local vendors seems more sustainable than throwing it away on chain restaurants and national department stores that never felt connected to community residents anyway. In a small way, the flea market has brought back some of that old holiday spirit I remember from my own time working in the neighborhood.

At the last flea market we attended, my son found a vintage button-down Ben Davis — another Frisco workwear staple — to go with the Timbs that he has yet to receive. Though I don’t consider my own pair vintage, I guess you can say those boots have walked many hills and seen a lot of change. Hopefully they’ll last long enough to live through a revitalization of downtown SF that is truly for the people who built it.

Sucka Flea’s pop-up holiday market will take place on Saturday, Dec. 16, 10 a.m.–4 p.m., at Howard Street and Embarcadero in San Francisco. The downtown pop-up is normally held at 332 Pine St. Its Mission District outpost will have its next event at CityStation SF (701 Valencia St.) on Jan. 14.


Rocky Rivera is a journalist, emcee, author and activist from San Francisco. She has four musical projects out, three of those with her label Beatrock Music. She released her first book last year, entitled Snakeskin: Essays by Rocky Rivera.

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