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One-on-One with Silicon Valley’s Enemy No. 1

Chesa Boudin
Gabrielle Lurie/SF Chronicle via Getty
Theodore Schleifer
March 29, 2022

Last Thursday evening, I hopped out of an Uber in San Francisco’s Mission District to kibitz among the tech-political menagerie at the launch party for The San Francisco Standard, a new, promising and buzzy publication that is particularly popular with the city’s civic-minded tech crowd and is chaired by the Sequoia venture capitalist and former journalist Mike Moritz, who is funding the outlet with $10 million. As I approached the door, about an hour after the event’s start time, I did a double-take as a tall, suit-clad man—a rare sight in these parts—and his entourage disembarked from their car at the exact same moment: Was that Chesa?

In some ways, I was surprised to see Chesa Boudin, San Francisco’s embattled District Attorney, at a party where he was likely to see not just fans but some of the business leaders who would like to toss him from office this June. (At one point later in the evening, I saw Chesa literally standing back-to-back, in separate conversation circles, with the political operative who is leading the largest outside group behind his recall.) But in other ways, I was not. Chesa is daring, irrepressible, and unafraid of the people lobbing tomatoes his way. Many tech elites have cast Chesa as an avatar of out-of-control progressivism, a hapless oaf who presides over San Francisco’s deterioration into a woke, crime-infested Hobbesian hellhole, in part because he has generally sought more lenient sentences and declined to prosecute some juveniles as adults. But the son of imprisoned 1970s radicals was precociously interested in reimagining the criminal justice system, even radically, well before he went to Yale Law or became a Rhodes Scholar. He is no slouch.