Categories: I Drive SF

What would Herb Caen say?

For over half a century, Herb Caen was the “voice and conscience” of San Francisco. In his daily column, Caen documented life in The City, from the Great Depression to the Grunge Era.

Reading a collection of his newspaper work is a different kind of history lesson. Like flipping through an old photo album and recognizing faces in faded snapshots that have been transformed over time, but familiar nonetheless.

Even though Caen frequently ruminated on the San Francisco of old, change is constant throughout his writings.

Of course, he saw it all. And if he didn’t witness it or hear about it first hand, he received a tip about it …

Upon securing this column three years ago, I remember being at the yard and telling Late Night Larry about my stroke of luck.

“Herb Caen,” he snarled. “Find his books. Read them. Cover-to-cover. If you need to borrow mine, let me know.”

Unfortunately, it wasn’t easy to locate Herb Caen’s books, most of which are out of print. For several weeks, while traversing The City in between fares, I went from one bookstore to the next. More disheartening than my futile quest, though, was when a bookstore clerk responded to my query with, “Who?”

Late at night, when the streets are empty, I will bemoan the lack of fares with other cab drivers. But secretly, I enjoy the solitude. It’s at these times that I feel most connected to The City and when I’m able to let me mind wander to ponder such frivolities such as, “What would Herb Caen think of all this?”

“What we know now,” he wrote in 1967, “for a fact, is that the more The City changes, the more it changes — it’s as simple and complicated as that.”

Change is inevitable, yes, but change isn’t always good, right? Since Caen hated the Transamerica Pyramid, I can’t help but wonder what he would think of the Salesforce Tower.

Herb Caen was no fan of the Beatniks but he seemed to think more highly of the hippies, writing in 1967, “As Voltaire might have said, if the hippies hadn’t existed, it would have been necessary to invent them.” Would he feel the same about techies?

While he witnessed the homeless population grow, and commented on the squalor repeatedly over the years (“Market and Filth,” he wrote in 1966, “as I sometimes think of it. Is there a dirtier, doggier, more trash-strewn [human and otherwise] stretch of retch in town?”), what would he say about the horror show on Market Street these days?

How about the recent news that a major medical association is moving their convention to Los Angeles, due to its members not feeling safe in The City, citing the blatant drug use, mental illness and homelessness that are constantly on display?

In 1964, he wrote, “A city, any city, is always in a state of anarchy, more or less controlled. For a city is the world — or the jungle — in microcosm, and the laws of the jungle prevail.”


I’m often struck by how selfish people have become. But that too, apparently, is nothing new.

“Let me get mine,” he continues in the same paragraph, “and then we’ll worry about the common good. As for what constitutes ‘mine,’ it’s every man for himself.”

Hmm. If I was hoping to find some validation for my impulse to blame everything on the current powers-that-be, reading The Best of Herb Caen, 1960-1975 is a total letdown.

It’s fascinating though. Like this gem: Staying contemporary is “a hard role to play in a city with a magnificent past, a restless present and a future whose outlines — square and graceless — are already discernible on a hilltop earmarked for leveling. This could, of course, be a golden age: it’s hard to know when you’re living in one. But I’d say the odds are against it unless you’re so damn contemporary you can find excitement in a traffic jam and poetry in the smog.”

He wrote that in 1966, but it’s just as relevant today. That same year he wrote this: “I’ve lived in this city, man and bore, for the better part of my wasted life, and I am now ready to concede that nothing is permanent here except change.”


“What would Herb Caen say?”

The same thing he was saying all along, it seems. Perhaps the real question is, “When will we hear what he’s saying?”

Kelly Dessaint is a San Francisco taxi driver. His zine “Behind the Wheel” is available at bookstores throughout The City, and a “What would Herb Caen say?” bumpersticker is available on his blog. Write to Kelly at or visit

Kelly Dessaint
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Kelly Dessaint

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