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Today, we’re taking a look at Silicon Valley’s next big political knife fight: the wild, well-funded effort to recall San Francisco District Attorney Chesa Boudin, and how tech money is shaping what will be one of the most important races of 2022.

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Tech’s Looming Radical Chic Throwdown

The recall election of Chesa Boudin, San Francisco’s avant-garde D.A., has turned bitter, pitting tech’s billionaires against one another—and forcing the city to look at itself, and its past, in the mirror.

Last January, I fired up my AirPods to eavesdrop on a Clubhouse thrashing of Chesa Boudin, the 41-year-old, bleeding heart District Attorney of San Francisco, and the son of the infamous Weather Underground radicals Kathy Boudin and David Gilbert. In those lonely, divisive days of the pandemic, one of the few ways that Silicon Valley could find companionship was bonding over how Chesa—who had achieved first-name only status like Sheryl or Elon—was absolutely not crushing it. 

Chesa, partly raised by his surrogate father Bill Ayers while his parents were incarcerated for an armed robbery gone awry, took the more establishment path to political power. Educated at Yale and Oxford, Boudin clerked on the U.S. Court of Appeals before becoming a public defender. Elected in 2019, he immediately became one of America’s most controversial prosecutors, deemphasizing placing non-violent criminals on trial. Chesa had struck a nerve in the city, a first-world utopia wrestling with social disorder, at a time of growing bipartisan outrage over mass incarceration, with a mandate to try something new. 

I was expecting the usual kvetch-fest on the Clubhouse virtual chat, with the anodyne title, “The Future of SF.” Complaining about Chesa, after all, had become a cherished pastime amid the post-Covid crime wave and the proliferation of viral robberies and assaults near some of the country’s most expensive zip codes. Did you see that video of the smash-and-grab in SOMA? Was he really best friends with Hugo Chavez? Have you read my Medium post? 

What I didn’t expect was for Chesa Boudin himself to somehow find the Clubhouse chatroom and, without any advance notice, give as good as he got. “The whole framework for these conversations is based on lies,” he said. Tempers flared and the listenership surged over the next half hour or so as the pugilistic D.A., armed with more-complicated statistics than Silicon Valley cared to admit, argued that the pandemic, not his own policies, was to blame for any rising crime nationally. 

For the moment, it seemed that Chesa had gained the rhetorical upper hand in the endless tug-of-war between the city’s Haight-Ashbury counterculture and the techno-libertarianism that is displacing it. But in the months since the Clubhouse smackdown, which has attained almost mythological status of its own, the situation in San Francisco, at least as depicted in the media, has been deteriorating...

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