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. 

And yet Chesa is, without a doubt, in serious trouble. The well-funded recall goes before an angry electorate this summer that just voted to toss three liberal members of its school board by a three-to-one margin, in a state that flirted with dethroning its Democratic governor, and appears fed up with the surge of crimes like burglaries and car thefts. The public data is cloudier than Chesa’s tech critics like to admit, but people perceive themselves to be more at risk of crime. I’ve had my own recent brushes with San Francisco crime —like many residents, my car was broken into about a year ago; unlike many residents, this year I served on a weeks-long violent criminal trial prosecuted by Chesa’s office, a fascinating experience. (The two sides eventually cut a deal.)