An Open Letter to William Oberndorf

Dimitry Yakoushkin
6 min readJun 18, 2022

No man is a monolith, but to contextualize you for others that will read this letter and not know who you are, there’s this: you donated $1.5M to Mitch McConnell’s 2022 campaign. I can only imagine the eye-roll that I rightfully deserve for condensing your rich, productive life to that singular tidbit, but one’s relationship to Mitch does tend to make for a quick assessment of a person. And we’re all pressed for time, amiright?

Since part of this letter is exposing your character, it’s only fair I expose part of mine. I root for villains in fiction. This is the best way I can explain my vice: the more powerful a villain, the more intense the story’s conflict becomes. I love heroes too, but I love them as underdogs, so I love a good villain even more. I’m obsessed with Homelander's simultaneous downward spiral into darkness and ascension to power. When an exhausted Luke left his hand exposed a little too long, I wanted Vader to lob it off. The thrilling part for me was not when Rocky was winning, but when he was so beat up that winning seemed impossible.

It is due to my need for a good story — good conflict — that I admire you. Nay, downright obsess over you. I’ve written satire before, but this isn’t that.

Our progressive DA Chesa Boudin was recently recalled as easily as Luke’s hand. You’ve admitted by way of being the main donor on the “Yes-on-H” contributors list that you are San Francisco’s father, or as close to being our father that your millions of PAC recall campaign donation can buy.

My underestimation of you began with the assumption that your name alone listed as a (substantial) donor on a campaign in San Francisco would assure its defeat— because what self-respecting SF Democrat would align themselves with *the* Republican donor? Turns out, a large majority would. I always forget most people will convince themselves that aligning with evil, if done for a “good” cause (i.e. “their” cause,) is worth it. The others that don’t believe this but still took your money? Well, those people obviously just enjoy cashing checks. The rest of SF doesn’t even know who you are, and that is even a more brilliant trick. Congrats.

Crime in SF is down in every category, yet friends have asked me about the “recent rash of car break-ins” and if it’s safe to park when they visit me — despite the fact that they’ve lived five miles away from me for years.

“Democrats” in SF are tweeting sensationalized Fox News stories about a woman attempting to kidnap children (it turns out she was a mom having a psychotic break while trying to pick up her own kids from school) and then falsely saying she’s at it again, and then tying it all back to Chesa’s responsibility with a completely made-up story.

What I’m saying here, and what I’m congratulating you on, is that your money has been put to good use; all of these beliefs originate from right-wing misinformation and “news” sites. My favorite was the website that looks and feels like the utterly wonderful “League of Pissed-Off Voters,” but is a Bizarro right-wing version that simply replaced “pissed-off” with “angry,” and then the smart google and Facebook ads that point SF-ers to this site. Whomever did that for you — give them a raise.

William Oberndorf — you’re not quite as handsome as Homelander, but you’re far smarter. Image © Amazon.

William, your understanding of people — particularly how lazy and uneducated and frighten-able even those with PhDs in the sciences are — greatly exceeds mine. It’s simultaneously thrilling and depressing how good you are at this. I’ve googled your net worth (the varying reports all place it at staggeringly high amounts) and I genuinely believe that in the particular way we’ve set up a capitalist society that you deserve every penny. I’m embarrassed to call myself a therapist when someone like you understands people and relationships far better than me. My son, my ex, and current partner all called me an "optimist,” but I’m only now realizing it’s just a nice way to say “stupid.”

So what I want you to do is have at it. Turn the screws further. $600k got you a 55% vote on a recall of a progressive official in San-Fran-fucking-cisco, a city that for the rest of the nation exists more as an adjective for liberalism than it does as a real place. You’ve got longtime SF residents clamoring to “make the city great again” (God I wish I wasn’t directly quoting an SF “Democrat’s” actual tweet.) William, consider me your man on the inside — I’m telling you as honestly as I can that everything you’re doing is working.

I want to see SF humiliated, defeated, and the rest of it kowtow to you and become a Republican majority. I want progressivism to become immoral and illegal and I want to actually hide in basements for our anti right-wing meetings. I want you to finish what you started. Don’t quit now, William. Don’t be a fucking coward and back down when you’ve got us on the ropes. You have billions.

Keep telling us crime is high and getting worse. Keep telling us to fight the war on drugs. Keep telling us that drugs and sex are bad and abstinence is the only way. Keep telling us that prosecuting the mentally ill and disenfranchised and victims is how to keep our streets safe. Feed us the lies we deserve. If we start to get out of line and defund the police, just do what you did last month and flood the news cycle with stories of car break-ins and overdoses. When the tough-on-crime moderate mayor appoints a new tough-on-crime moderate DA and they cozy up with the new conservative-SF “majority,” flood the news cycle with sunshine. Show our happy, safe communities and the many arrests that got us there. Law and order, William, law and fucking order. Make our city great again.

My uncle fought with the 101st Airborne in the Battle of the Bulge. Like him, I want to tell kids two generations below me stories that I literally fought Nazis and won. Like I said, I love a good villain and underdog story.

Roll your eyes, William Obernorf and pro-recall campaign chair Mary Jung and David Sacks and Michael Moritz and you light-brown shirts over at GrowSF and misery pornographers-tuned political activists Tom Wolf and the rest of you pro-recall SF Republicans, because this does sound pretty ridiculous. After all, your boy Trump’s January 6th Reichstag fire attempt fizzled out and our version of a (kinda) democratic 1933 Germany never got to grow into our version of a fascist 1942 Germany.

But there’s hope yet, William, because what if the next guy isn’t a spray-tanned inept bumblefuck? (Huge hint: DeSantis likes his checks written out to “Cash” and his third-grade teachers arrested for saying “gay.”) The Russian legislature recently voted 474–0 in alignment with Putin’s calls to ban any gay propaganda — ostensibly in an effort to protect their children, too. And Putin’s approval rating is 100%. You can’t buy an approval like that! Oh wait, actually you can. And you, as in actually you, William, can.

I want to be clear, here however— I’m not calling you a fascist or a Nazi. I’m saying you knowingly and happily fund them.

William, I hope that you die a very very old, very very rich man. I hope you outlive all of your loved ones and you spend your last moments alone in a dark, cold hospital room in the kind of abject terror only pure loneliness can yield. I hope the final few people in your life are the surgeons that spend their time tearing out your cancers and your rot and your failing joints and organs until there’s barely a body left. I hope that the last gurgled words escaping your one remaining fluid-filled lung — words that no one will ever hear — are for mommy, or anyone, to take the horrible pain away as you slowly, ever so slowly drown in your own puss and lymph. But until then, stay strong and wreck my fucking city, daddy.

--

--