Browsing through Amazon (don’t judge) we found a novel published last year that caught our attention. “Stilettos and Steel” by Jeri Estes is a noir-esque crime novel based on her personal experiences living in the Tenderloin in the mid-1960s as a runaway teen from the Southern California suburbs. With nowhere to go, she lands in “a seedy neighborhood run by dirty cops and ruthless gangsters”. She briefly tries her hand at prostitution, but quickly promotes herself to management and becomes a pimp. That doesn’t sit so well with the men who rule the Tenderloin. They are determined to run the new pretender off the block and out of the city entirely. The only problem is, they didn’t count on facing off with a whole gang of gorgeous hookers who won’t be ordered around anymore. The new stud on the block is a lot nicer, and she pays a lot better.

“Stilettos and Steel” also chronicles a first in LGBT history that took place in the Tenderloin in 1966: The Compton’s Cafeteria Riot, where the gay community fought police harassment in San Francisco’s Tenderloin three years before the more famous riot at the Stonewall Inn bar in NYC. This is how Jeri Estes describes it in the book:

The cafeteria was on Turk and Taylor Street was my favorite place to rendezvous. It was a convenient meeting spot in the heart of the Tenderloin. Any time was a good time, since it was open twenty-four, seven. The corner was a mecca for every variety of street people, including the young runaways who panhandled in front of the restaurant.

Compton’s had large windows that ran the full length of the cafeteria, which made it an ideal location to check out the street action. The cooks and servers were were immune to the hard drag butches, to the dolled-up femmes, flamboyant queens and army of hippies and bikers that lingered inside over cups of coffee.

To give you a better idea of ho the Tenderloin was perceived in the 1960s, here’s a TV report in which it gets called “a marketplace of vice, degradation and human misery”:

The book has stellar reviews on Amazon, so we’ll have to check it out. Here’s an excerpt from the opening chapter, titled “Welcome to the Tenderloin”:

Turned the corner on Ellis and Powell Streets with a red rose in my hand. The chilly night air stole through my silk shirt as I made my way to the Why Not Lounge. Sporting a new leather jacket and polished wing tips, I rehearsed my best clean-up lines. Carmen knew me too well for just anything to work.
At this hour, the heart of San Francisco came alive with romance and glamor. Antique fog lamps softly illuminated the sidewalks. Other suitors walked arm in arm with their girls through Union Square. Shiny black limos dropped off well-heeled travelers draped in minks, diamonds and tailored overcoats. Glowing candles on white linen peeked through the windows of the five-star restaurants. Grand facades of elegant shops and historic hotels lent the streets a Parisian grandeur.

As I neared the Tenderloin, the neighborhood lost its civility. Flower-crowned hippies, restless soldiers and glossy ladies of the night emerged from the mist. Strip joints, beer bars and panhandlers announced the opening of San Francisco’s red light district. It welcomed runaways from all over, people like me who didn’t fit in at home.