By Mauricio Segura June 18, 2025
Photo: Webador Stock
San Francisco wears its history like a patchwork jacket, some parts polished, others tattered, and many stitched with stories that rarely make the guidebooks. While the city’s skyline and foggy hills are instantly recognizable, its lesser-known past tells a far richer tale, one that’s as gritty and weird as it is fascinating.
Let’s start with Ah Toy, the city’s first infamous courtesan. She arrived from China in 1849 during the Gold Rush and quickly turned heads, and profits. Charging eager miners “two bits for a lookee, four bits for a feelee,” Ah Toy reportedly made a fortune by simply flirting, often without ever undressing. Later, she ran a string of brothels and even took men to court who challenged her business. Long before Silicon Valley billionaires, she proved that San Francisco was fertile ground for sharp minds and bolder spirits.
And speaking of fertile ground, there wasn’t any. Much of what is now western San Francisco, including Golden Gate Park, was once nothing but sand dunes. When early city planners decided to tame the dunes, they planted thousands of trees, hoping roots would stabilize the ground. It took years of trial and error, but eventually the sand gave way to grass, gardens, and greenery. The park’s current beauty masks a long, gritty battle against nature.
Long before tech giants staked out office towers, San Francisco’s intellectuals found a home in the Montgomery Block. Built in 1853, this four-story brick structure was called “Halleck’s Folly” because people thought it would collapse under its own weight. Instead, it survived the 1906 earthquake and became the West’s literary nerve center. Jack London, Mark Twain, and Ambrose Bierce all worked or drank there. Despite its durability, the building was razed in 1959 to make way for the now-iconic Transamerica Pyramid, progress swallowing history whole.
After the earthquake and fire of 1906 reduced most of downtown to rubble, the city’s commercial core temporarily shifted to the Fillmore District. What rose there was more than a shopping district, it became a cultural crossroads for Japanese Americans, African Americans, and Jewish communities. It would go on to birth jazz clubs, soul food joints, and synagogues, earning the nickname “Harlem of the West.” Sadly, much of this vibrancy was bulldozed during the so-called “urban renewal” projects of the 1960s.
San Francisco’s roughest edge was the Barbary Coast, a bawdy, brawling nine-block stretch infamous for brothels, saloons, dance halls, and swindlers. During the Gold Rush, desperate miners flooded the area, and the “Sydney Ducks”, an Australian gang, took full advantage, reportedly lighting fires to distract while they looted. Eventually, a group of armed citizens formed a vigilante committee to drive the Ducks out, proving the city has always had a flair for self-policing, for better or worse.
The Tenderloin, often maligned, also deserves its due. Long before it was synonymous with grit, it was the beating heart of San Francisco’s underground culture. Gambling dens, speakeasies, and theaters thrived here. In 1966, three years before the Stonewall riots in New York, transgender patrons at Compton’s Cafeteria fought back against a police raid, igniting one of the first known LGBTQ+ uprisings in U.S. history. It was messy, defiant, and historic, very San Francisco.
Other queer landmarks made their mark, too. In 1961, police raided the Tay-Bush Inn and arrested over 100 gay men in what became a galvanizing moment for the city’s LGBTQ+ movement. But the Black Cat Bar might be the most iconic of all. Reopened after Prohibition in 1933, it attracted everyone from beat poets to drag queens. Owner Sol Stoumen fought all the way to the California Supreme Court in 1951 to defend the bar’s right to serve openly gay patrons, winning a key legal victory years ahead of its time. It finally closed in 1964, but not before laying the groundwork for decades of activism.
San Francisco has always been a city in flux, burning, rebuilding, transforming. But through it all, it has retained its spirit: a place where people push boundaries, challenge authority, and rewrite the rules. You won’t find these stories on postcards, but they’re etched into the soul of the city. All you have to do is look a little closer.
