Welcome back to the Reasonable Efforts newsletter, where we explore the week’s news through the art of argument. This week, as last, I argue for optimism after another uniquely bleak week.
I was going to write about the Parler Purge, and about freedom of speech. But then, just before I pressed Publish, something amazing happened: I bore witness, together with 2,500 of my neighbors, to a heated argument on social media between two rival political factions — and, (miracle of miracles!) everyone involved came out looking substantially better than when they came in. Against all odds, in this, the year 2021, my neighbors and I became better informed citizens.
I know. I know!
So, we’ll talk about freedom of speech next week (maybe), because this week, we’re talking about miracles.
One week after our federal politics devolved into the executive branch sending a lynch mob to the legislative branch, thousands of San Franciscans logged onto a social media platform and witnessed the impossible: political opponents having a reasoned, informative discussion in front of their constituents, with both sides engaging in (mostly) good faith and neither side compromising on their ideology. It was nothing short of a pigs-with-wings miracle.
It’s shocking that such a thing happened on social media, and it’s even more shocking because it could have only happened on, and because of, social media. Could it be that the industry everyone blames for destroying national politics will be the one to save local politics?
It started out innocuously enough, with an invite on Twitter to a talk on Clubhouse:
Clubhouse is a relatively new, audio-only platform where people can host conversations in “rooms” that anyone else can discover and join. Michelle Tandler and Mike Solana are both passionate San Franciscans within a network of increasingly political members of the tech/VC communities. They’ve written extensively and thoughtfully about the problems and potential of San Francisco, and they’ve increasingly focused their ire on one political rival in particular: the District Attorney, Chesa Boudin.
Michelle and Mike opened the room, titled “The Future of SF”, and invited several political allies to the conversation, most notably: Nancy Tung, who ran against Chesa Boudin in the 2019 election; and Cyan Banister, chair of the Recall Chesa campaign.
I joined early, when the room had about 40 or so people in the audience. Mike and Michelle began with a discussion of the uniquely San Franciscan political spectrum, where the left-center-right positions are occupied by the Democratic Socialists of America, the Progressives, and the Moderates, respectively. To state the obvious: that’s incredibly tilted, where the “left” is occupied by unapologetic Maoists and the “right” is occupied by Nancy Pelosi. Mike and Michelle are Moderates, and were explaining to the growing audience that Chesa—who has a very public history of supporting Hugo Chavez—sits on the far, far left of that spectrum.
It was then that Chesa Boudin logged on and quietly sat in the audience.
After a few minutes, the moderators noticed. Mike and Michelle invited Chesa into the hornet’s nest by giving him speaking privileges and, to Chesa’s immense credit, he accepted.
The stage was set for an absolute shitshow: an embattled politician joined a conference call of his ideological rivals—including his opponent in the last election, and the leader of the effort to recall him before the next one—in front of a growing audience of his (increasingly angry) constituents.
My first thought was “I should make popcorn”, so I did.
Chesa came out swinging. He joined the conversation, he said, because someone had tipped him off that he was being dragged, misrepresented, and slandered by out-of-touch billionaires with no interest in the truth, and no interest in improving San Francisco. Mike punched back, demanding to know whether Chesa still supports the politics of Comrade Chavez. Chesa parried by denying he had ever met Chavez (which, notably, did not answer Mike’s question), and the shitshow was starting to steam. Chesa dominated the conversation, talking over questions and spending way too much time insulting Mike for reading Wikipedia.
Michelle sensed the opportunity and rescued the conversation. She thanked Chesa for his bravery, and let him know that everyone in the room only cares about his policies and his ideology because we care about San Francisco. Because we’re victims of robberies, because we’re terrified of violence, because his approach to prosecution appears to let career criminals back onto our streets to rob and kill.
Then, the miracle: Chesa dropped his guard, Mike calmed his fervor, and an honest and impromptu town hall in front of over 2,500 concerned constituents began.
For the next hour, Chesa answered difficult and probing questions from respected members of the San Francisco tech community. He gave incredibly detailed accounts of institutional failures and bureaucratic sclerosis. He painted a picture of decades of incompetence, corruption, and mismanagement in city government, of himself as a patient and earnest fighter for justice in a broken system.
He also deflected, reframed, and evaded, pointing fingers at everyone from prior District Attorneys to career prosecutors to the Mayor to the Board of Supervisors to the SFPD to venture capitalists to (again, weirdly) Wikipedia. Michelle, Mike, and their fellow moderators were entirely unprepared, and it showed, but they did a surprisingly good job highlighting Chesa’s complete refusal to discuss his ideology—that is, the very core of his constituent’s concerns with him.
After about an hour, another surprise guest joined the room: Balaji Srinivasan, a shrewd and savvy doomsayer of San Francisco and fierce critic of Chesa’s politics.
Unlike the other gobsmacked moderators, Balaji has never been unprepared in his life, and within five minutes he began to box Chesa in, preventing him from shifting blame to others for the thousands of discretionary decisions he makes every day. Chesa, sensing a shift in the room, wisely ended the impromptu town hall.
I left the conversation elated and inspired—not by Chesa, whose politics I loathe—but by the entire event. Before that night, I saw Clubhouse as nothing more than live-action podcasts, but now I think I get it: Clubhouse is social media as a town hall, rather than a public square.
Local politics in America suffers for many reasons, but a major one is that the political conversation has died. More accurately, it moved online, but that’s pretty much the same thing, historically. Online political conversations necessarily expand in scope, which makes their focus increasingly national and international. As interest in local politics wanes, local journalism suffers, and without local journalism framing the issues, our neighborly conversations become as fractured as our national ones. But something about live audio, something about real-time conversation, something about the fluidity of social media, seems capable of piecing those neighborly conversations back together. I heard it happen, live.
We can imagine the opposite, of course. Dropping someone like, say, Donald Trump into a Clubhouse room would create a familiar sort of bedlam, and opportunists may yet ruin that platform, too. But unlike the current crop of social media spaces that reward broadcasting, Clubhouse rewards conversation, so maybe Clubhouse will be more likely to expose political grifters than elevate them. It could also be that, as the platform grows, politicians hide out exclusively in friendly rooms, recreating the echo chamber dynamic.
No one can know for sure. But, while I’m still not sure what exactly happened last night, I do know this: social media still has tremendous potential to revolutionize our politics and society for the better. An impromptu discussion between political rivals like that is simply inconceivable in any other context. An impromptu conversation In Real Life can’t attract a crowd of constituents like it can on social media. A scheduled conversation In Real Life is just the familiar old sanitized “town hall debate” we know and hate. Only on social media could such an event take place. I hope Paul and Rohan see the potential of what they created, and I hope we all get to see them realize it.
For the Mikes and Michelles and Cyans of San Francisco, a few parting thoughts:
Welcome to politics! The tech/VC communities in San Francisco are populated with political novices, and it was painfully obvious last night. Techies are often criticized for hubristically claiming expertise over fields they know nothing about—unfairly, in most cases—but that was on full display last night. With the obvious exception of Nancy Tung (who, despite being overshadowed by Chesa’s monologuing, was the unsung superstar of the night), their ignorance of municipal politics and legal process made it difficult for them to engage on Chesa’s level. They’ll need to bring many more politicos and lawyers (hey, hello, that’s me, I’m a lawyer, pick me) into their movement if they’re going to save San Francisco.
Chesa Boudin is a shitty DA, but a brilliant politician. Chesa put on a masterclass in political gamesmanship last night. His deflections were Clintonian—subtle enough that you’d think he answered the question, savvy enough that you’d find yourself agreeing with him that the problem is someone else’s fault. His politics are probably too extreme to go national (probably), but he will be a standard-bearer for the far left in California for the next forty years. We’d better get used to him.
Journalism is a deeply valuable and important skill, when actually practiced. Mike, Michelle, and the moderators were simply outmatched by Chesa’s talent for PR. Chesa’s slipperiness made clear how important talented journalists are to a culture of political accountability. Unfortunately, modern journalism has devolved mostly into clickbait and tabloids, and modern journalists into edgelords and grievance farmers. Local politics can be reinvigorated by direct conversations between political opponents in front of constituents, but the conversations can only go so far without journalists doing what they do best: pinning down rhetorically gifted politicians, and carefully extracting answers from them.
The biggest problem with local politics in American cities is the Machine. If Chesa and Mike could find any common ground, it might be this: San Francisco is being strangled to death by a landed gentry supporting a sclerotic, byzantine bureaucracy that stands for nothing but increasing property values. By his own admission, this Machine prevents Chesa from enacting his socialistic reforms, just as it prevents Mike from realizing his technocratic ones. It’s time to rage against that Machine, not just each other.
Thanks again for reading, and I’ll see you next week!
LOVE,
MIKE