29 Sunset Missives

Blog/newsletter by David 29 Sunset • 29sunset.comrssreceive new posts as email newslettercontact

Jose Caballero Follows the Rules and MLB Doesn't Like It

July 23, 2026


Generally, I’m a rules-follower. I don’t cut lines. I use crosswalks. I pay transit fares even when I know no one’s checking. Abiding by agreements is valuable because when fewer people honor just agreements — which is what most rules boil down to — then trust degrades and that way lies disorder, chaos, and misery. Which brings me to Yankees utility player Jose Caballero and MLB’s pitch clock.

The Limiting Vision of "Revitalizing Downtown"

June 28, 2026


Recently, I visited Portland, Oregon, and Seattle to see family and friends, and to be in town during the US Men’s National Team World Cup game against Australia. I had visited both cities previously, but it had been a few years, and since then I’ve learned a lot about urban development and evolved on what I value in places — both places to live and to visit.

I wasn’t there to pass judgment on whether Portland and Seattle are “good,” but my experiences did prompt me to think a lot about San Francisco’s mayor, Daniel Lurie, and the anxieties about my city that apparently motivate a good chunk of its leadership, which in turn get transferred to media members and everyday people who take their cues from those leaders.

Catching Up With Catchers Who DH

June 21, 2026


Last August, I noticed that Major League Baseball teams were using catchers as designated hitters more often than in previous years, so I attempted to quantify and contextualize the trend. Through Saturday’s games, most teams were just shy of the halfway mark in the season, so I counted again.

The topline takeaway: Teams are starting catchers at DH at higher rates than they have in recent years, and at a higher rate than any other season for which I’ve checked the numbers.

Make the NBA Draft Lottery a Mini-game

May 25, 2026


This weekend, Brentford missed European football for next season after they failed to convert an open header in the 100th minute of their final day match against Liverpool. That feels terrible right now, but before this season, the Bees were widely picked as a relegation candidate after transitioning away from their top two goal scorers and manager from the previous season. Instead, they simply kept on doing what they do, matching their highest-ever finish since returning to the English Premier League in 2021-22 and generally having solid vibes. Be resilient and formidable like Brentford. Don’t be expensive and nonsensical, like Tottenham.

This week, I wrote about my wild NBA Draft Lottery idea, my wild MLB roster construction idea, my super-easy lentils preparation, and more. LFG.

GO DIRECTLY TO
- Improving the NBA Draft Lottery
- The San Francisco Giants Have Been a Boring Kind of Bad
- Do Not Ever Let the Casino Into Your Pocket
- I Almost Hit a Home Run
- The Root of Anti-AI Rage
- Lentils: Hell, Yeah
- What Makes a “Top 15 TV Show”
- “The Ten Year Affair”

Trump Follows Classic Wrestling Logic

April 19, 2026


I did actually notice that the NBA playoffs began this past weekend, but I only watched a little bit because in my middle age I’ve once again become much more of a Baseball Guy, more interested in watching the end of a regular season Padres-Angels game than a Celtics-76ers first round playoff tilt. I’ll probably get drawn in during the conference finals.

This week, I wrote about Donald Trump’s pro wrestling persona, one’s dominant eye, “Project Hail Mary”, a great baseball book from the 1970s, my recent trip to Ireland, and more. LFG.

GO DIRECTLY TO
- Trump’s Pro Wrestling Logic
- “The Summer Game” by Roger Angell
- Do You Know Your Dominant Eye? What About Baseball Players?
- MLBGuessr
- The Helen DeWitt Drama
- Slop Is Not Inevitable; You Don’t Have to Use It
- “Project Hail Mary” by Andy Weir
- Ireland

I Want to Know if AI Is a Washing Machine

March 22, 2026


This week, I wrote something a bit longer about how my opinion of using AI is evolving as I learn new information. The TL;DR is that I’m trying not to be a kneejerk opponent of new technologies, but the more I see of what AI is, the more I’m convinced its most valuable utility is extremely narrow. Aside from that, I wrote about a rich person saying bad things, a cool chase video, and my redesigned website. LFG.

GO DIRECTLY TO:
- I Want to Know if AI Is a Washing Machine
- Rich People Are Not Necessarily Smart: Exhibit Bajillion
- “A Miraculous Escape”
- The Climate Apocalypse Continues
- It’s Time For Baseball
- My Home Page Is a Motherfucking Website

Driving Like a Maniac Should Have Consequences

February 22, 2026


The Winter Olympics are basically over as I write this, and I didn’t watch much of it, though I did notice that drone footage following downhill skiers kicks ass. I understand various safety concerns, but at a certain point, one wonders why drones aren’t used more extensively over soccer matches, baseball games, and other outdoor sporting events where cable-guided cameras over the playing surface are impractical.

This month, I’ve written about a cool philosophy book, how I've been radicalized against cars, a critically-acclaimed TV show I’m finally watching, Barack Obama’s opinion on aliens, our gambling dystopia, and more. LFG.

GO DIRECTLY TO:
Are You Competitive? Know “The Score”
Which MLB Teams Are Trying to Win?
American Gambling Culture Is Bad
“Halt and Catch Fire”
Driving Like a Maniac Should Have Consequences
The Worst Class I Took in College
Barack Obama Got Asked About Aliens…
Sam Altman Doesn’t Value Humanity
A Good Toilet Seat
More About My Next Book

Do Not Mess With Calvin and Hobbes

December 21, 2025


I hope you’re having a safe and happy holiday season. For the last entry of 2025, I’m sharing some reflections on “Wake Up Dead Man,” Jeff Kent, cookies, books, tying shoes, Calvin and Hobbes, and more. It’s the most wonderful time of the year, and that means I’m only giving you the uncut best stuff I’ve got. Also, the first season of the Kids Popcorn Podcast is finished! Listen to all the episodes on the podcast site, or wherever you get your podcasts. LFG.

GO DIRECTLY TO:
Read My Novel for Free
“Wake Up Dead Man” Is an Intensely Catholic Movie
Chatbots Aren’t Your Friends
Seriously, the Jeff Kent “Survivor” Clip Is Hilarious
Step Up Your Cookie Game
Do Not Mess With Calvin and Hobbes
“Now That I’m Grown, I Eat Five Dozen Eggs”
“So This Is Christmas”
The Greatest TED Talk Ever
All the Books I’ve Read This Year

Mamdani Beyond New York

November 23, 2025


We’re currently in the midst of the first season of the Kids Popcorn Podcast, my show in which I interview interesting people about the movies they watched as kids and kids movies they find interesting as adults. If you want to listen to Zach Geballe talk about toxic parental traits in “Tangled,” Maria Bustillos talking about watching “The Sound of Music” dubbed in Spanish, or Gabe Fernandez reflecting on why he watched so much “Bruce Almighty” as a child, and more, you can hear those episodes and find subscription links at the Kids Popcorn Podcast website.

In this post, I wrote about Zohran Mamdani, bagels, Victor Wembanyama, the World Series, “Our Town”, "Wicked", and more. LFG.

GO DIRECTLY TO:
- Mamdani Beyond New York
- Such a Great World Series
- Wemby
- “Our Town”
- NYC Bagels, SF Bagels, Las Vegas Bagels
- MrBeast Sucks
- A Great Expository Movie Scene
- Wicked For… Meh
- New Nightmare App Dropped
- Through 4 Episodes of “Pluribus”…

"Great Comedians Get Away With It"

October 20, 2025


First things first… I’ve been working on a new project I’m proud to share: the Kids Popcorn Podcast. In each episode, I interview an interesting person about movies they watched as kids and the kids movies they find interesting today. The first episode drops Oct. 27, 2025, so I hope you subscribe through the links on popcorn.29sunset.com or wherever you get your podcasts.

While I’ve happily devoted lot of my attention to the podcast in recent weeks, there’s plenty more to notice in the world. Below, I’ve written about the No Kings protests, a skillful Trevor Noah comedy set, a take on “One Battle After Another” I’m guessing you haven’t seen, a trash prestige TV show, why the New York Mets’ season was honorable, and more. LFG.

- No Kings
- “Great Comedians Get Away With It”
- Edgelord Shooters
- DEI by Other Names
- An Underappreciated Aspect of “One Battle After Another”
- Trash Prestige TV
- Finally Learned My Lesson on Stephen King
- Don’t You Dare “LOLMets”
- “The Compound Interest of Design”

Unctuous Grievance, Not a Good Look

September 21, 2025


Let he who has not gone on television and suggested killing all unhoused people be the first to cast a stone. Wait… why do you all have stones? Before things get out of hand, take a look below, where I’ve written about right-wingers’ contempt for the rule of law, the folly of car culture, a brief examination of Taylor Swift lyrics, and more. LFG.

GO DIRECTLY TO:
- Seeing Charlie Kirk with Clear Eyes
- Bari Weiss Is Not a Serious Person
- The U.S Government Keeps Bragging About Killing People for No Reason
- MAGA Has Contempt for the First Amendment
- By the Way, a Fox News Host Said We Should Solve Homelessness by Killing Unhoused People
- Car Culture Is the Worst, Pt. 1
- Car Culture Is the Worst, Pt. 2
- Reflecting on Roberto Clemente Day
- The Clippers Are Showing Why Salary Caps Are Bad
- A Thought About Taylor Swift’s Lyrics
- I Recommend a Novel: “When We Were Real”

AI Evangelism is a Hazard to Your Health

May 18, 2025

Hello, again. Have you ever had a moment where you heard someone say, or read about someone saying, something utterly bizarre and you realized instantly they had no idea that what they were saying was completely bonkers? I feel like I have two or three of those every week, now.

Recently, I have been thinking about AI evangelism cooking people’s brains and why “Andor” is the greatest Star Wars story ever told. I have also come up with an idea for a new Major League Baseball award, gave up reading a book because its anachronisms drove me to distraction, and have an important recommendation. LFG.

GO DIRECTLY TO:
AI Evangelists Cooking Their Brains
Using an AI-Created Video of a Dead Man in Court
Men Being Hot
Rob Manfred Sucks, Part Bajillion
My Pitch for a New MLB Fielding Award
A Book I Love
A Book I Didn’t Love, and Some History
Watch "Andor" Now
A Recommendation
A Reminder

The Grid... It Is Immaculate!

April 21, 2025


Hello, again. I have big news: My novel is published! It’s called “A Hell of a Wedding”. If you want to buy it in paperback, here’s where you can get it, and if you want a digital copy, you’re welcome to buy it, but I’m also happy to send you a free copy if you request it here. I’m proud of making this and hope it will find at least a few readers, so I hope you enjoy!

Recently, I have been appreciating Immaculate Grid and lamenting Americans’ seeming disregard for due process. I also read a really gossipy book about Elon Musk and read another book that deals with time travel in a satisfying way. LFG.

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