By Josh Gondelman — 08 Sep 2025

#148. Kawhi Leonard and You

They are NOT talking about trees! (Jayne Kamin-Oncea-Imagn Images)

Hi everyone,

After a great Maris's Birthday Week, we're back doing Regular Monday Stuff. I had a bunch of late nights out last week performing on and hanging out at shows, and I could feel my body getting slightly run down. Usually I'd have the good sense to cancel or reschedule something under those circumstances, but the last few times I did that, I just ended up at home feeling crummy instead of out feeling crummy. So, learning the exact wrong lesson, I pushed through and did everything I had on my calendar, and things ended up more or less fine. Latching onto incorrect takeaways from an experience and suffering no consequences? What am I, a CEO? Folks!

I am, of course, not a CEO. In fact, on Saturday I marched in the week-late-as-usual Labor Day parade. Weirdly, I don't think I'd ever made it to the parade before. I mean, it's not that weird. I don't attend that many parades overall. But I'm wrapping up my third term/sixth year in the Writers Guild of America East elected leadership, and I wanted to make sure I'm still doing what I can to be involved in union activities, so I set aside the morning to take a little walk through midtown with some yelling mixed in. The best part of the parade was marching alongside people from all corners of the labor movement. The funniest part was a protester outside of Trump Tower with a sign that just said:

"EPSTEIN! EPSTEIN! EPSTEIN! EPSTEIN!" Sadly I didn't get a picture of that.

A picture of me and Liz Hynes and Susan Rinkunas marching in the Labor Day Parade! — Please ignore how sweaty I am. (Photo credit: Farhad J. Parsa)

In other labor-adjacent news, I felt encouraged by the $1.5 billion dollar settlement reached by the group of authors who sued Anthropic (an AI company whose large language model was trained on hundreds of thousands of copyrighted works). I'm honestly still reading up on the wider implications of this lawsuit (and whether the best more for authors is to take their share of the settlement money), but it gave me a flicker of hope to see such a big penalty levied against one of these companies. Sometimes the best you can hope for in a given moment is a bad thing happening to a bad person or company. It should be noted that an individual artist taking this much material without owning the intellectual property and raising billions of dollars of funds off of that practice would be sued until they physically left the ground like they were being hit with a 37-punch Tekken combo. So I got to indulge in a bunch of good AI haterism this week, which warmed my spiteful heart.

I also heard maybe the saddest AI-adjacent thing of my life so far. While I was standing at a concert, I overheard heard a guy behind me say to the woman he was with: "Did I show you the video I had AI make of my high school band playing?" And look. I agree that it's neat that computers can do all sorts of things that would have felt like science fiction when I was a kid. I also understand the seductive lure of nostalgia. But it really bummed me out to hear someone so enthusiastic for a piece of software to create him a fully fabricated memory. He might as well have had AI generate footage from the first dance at his wedding to Marilyn Monroe. Yeah, a computer can show you believable fabricated footage of things. I'm sure there are no terrible far reaching implications of this technology that outweigh your brief flicker of: "Hey cool that's sorta me!"

Regardless! Thanks so much to everyone who came out to this week's Frankenstein's Baby (where I had a great time hanging out and enjoying the show) and everyone who braved the weather to make it out to Sup, Bro? on Saturday night. Alison Leiby and I had the best time hosting that one! Unrelated to the live show, Leiby and I are in the midst of a (hopefully brief) period of professional waiting. We're not yet in a place where the hope is for GOOD news, but I will gladly accept any mental energy you have to spare as we cross our fingers for news that isn't actively bad. I always roll my eyes at cryptic "more news soon" posts on social media, but this isn't a particularly interesting juncture to explain, and when I have interesting news (good or bad) to share, I'll tell that story here!

Oh! I was on MSNBC last night making some jokes about our horrible reality! I was going to include a clip here, but I don't think there are any online yet! I also Remembered Some Guys with the great team at Defector and am not sure if that's anywhere you can see it! It was a blast though!

This week:

Friday: I'm hosting Wait Wait...Don't Tell Me Presents: Comedy Grab Bag at the Bell House in Brooklyn! There are just a few tickets left and I think it's going to sell out!

Saturday: I'm headlining the Fairfield Comedy Circle in Connecticut! I imagine there are way more tickets left for that show.

Sunday: I'm the guest at the Boston tour stop of the Normal Gossip live show. It's at the Wilbur Theater and there may not be any tickets left?

Next Monday I'm going to be hanging out at the PUP/Jeff Rosenstock/Ekko Astral show in Boston I think! See you there, Bostonians?

Later this fall:

I'll be in New Orleans on 10/24 and 10/25 headlining Sports Drink once again! It's a great and cozy venue, and I'm so excited to bring my new jokes to town!

I'm coming back to Minneapolis on 11/23 (the Sunday before Thanksgiving) for one show only at the Parkway Theater, another venue and city I LOVE!

PEP TALK FOR KAWHI LEONARD

Kawhi Leonard in a Clippers jersey talking to Steve Ballmer who is facing away from the camera. — I hope he doesn't arbor a grudge. We have fun here. (Jayne Kamin-Oncea-Imagn Images)

I understand that not everyone who reads this newsletter is a lover of professional sports, and of the people who are, only a portion of those are NBA fans, and of those people only a few are keyed into the ups and downs of the offseason when there's little NBA news to talk about (and the WNBA is in full swing!). BUT STAY WITH ME...

Last week on his YouTube series/podcast (what do we call these things now?) Pablo Torre Finds Out, the titular Pablo Torre broke a story alleging that Clippers star Kawhi Leonard received an $28 million endorsement deal from a "tree brokerage" company called Aspiration that team owner Steve Ballmer had invested money in. I know this is a lot of information up front and seems potentially too boring to parse, but I SAID STAY WITH ME!!!! Here's a little primer...

Steve Ballmer is the owner of the Los Angeles Clippers (a professional basketball team). He was also the CEO of Microsoft from 2000-2014 and is consequently the wealthiest team owner in the NBA. He's worth $153 billion dollars give or take a few billion depending on which way the wind blows or what tariffs have been declared on a whim. In today's political and economic climate, people would be clambering to devour Ballmer's flesh in the streets, except that he pours a TON of money into the team and their facilities, and the Clippers' previous owner was an extraordinarily vile racist even by Trump Era standards. He is technically still alive, and it's kind of amazing that he hasn't been made Ambassador to the Philippines or something.
Kawhi Leonard is a an extremely talented basketball player and two-time NBA champion. He is known for having the kind of stoic personality you'd expect from a cowboy having a wound stitched up by a local tailor, looking down at it through clenched teeth, and flatly saying: "I reckon that'll do." This is an apt metaphor because Leonard is frequently injured. Leonard's taciturn nature is also notable here because despite taking in somewhere between $28 and $48 million dollars for this endorsement deal, he never mentioned Aspiration (or even really the concept of husbandry) in public. Not the most effective tactic as a spokesperson. Although it is one I'd like to see Kevin Hart try, just for the sake of giving us all a respite from his sports betting ads.
I am unclear on what a "tree brokerage" is (I'm kind of picturing those big arboreal suckers from Lord of the Rings on landline phones yelling "buy!" and "sell!" but who knows). I think it had something to do with...planting trees. Ultimately it doesn't matter. The company was some kind of scam, and the co-founder has pleaded guilty to fraud charges.

For what it's worth, Leonardo DiCaprio and Robert Downey Jr. were also somehow involved in Aspiration, but I don't think in any kind of criminal way. It seems like they were duped. Honestly, I am surprised by this part. Leonardo DiCaprio seems like he would have been much easier to trick back when he was desperate for an Oscar and you probably could have gotten him to live in an aquarium tank full of tapioca for a month if he thought it would get him the award. Frankly, I admire his commitment. Drake also endorsed Aspiration. I guess he just loves trees, although Kendrick Lamar would probably say he's more into saplings.
Why this is a big deal: To put it in the simplest terms, the NBA has a salary cap, which means teams only have a certain amount that they're allowed to pay their players every year. This is an anti-labor provision, which sounds counter-intuitive given how much money these players can make, until you realize the guys signing their checks are way, way richer. The salary cap is designed so that reality-alteringly rich guys like Steve Ballmer have less of an advantage over the other, still-obscenely-rich team owners. Otherwise, one person could presumably assemble the NBA version of Mr. Burns's company softball team of all the best players and dominate the league. Ballmer's investment in Aspiration and their subsequent endorsement deal with Kawhi Leonard is being investigated as a potential way to pay a player tens of millions of dollars more or less under the table. The company was allegedly less invested in green energy solutions than in solutions to provide a little more green energy if you catch my drift.

My friend Katie Heindl has already written a little about what makes this scandal so funny. No one seems to have been physically harmed. It involves very rich people either being or pretending to be stupid to avoid consequences. And most of all, it all centers on a fraudulent company that was purportedly just...planting trees. But they were not. Any rumors of horticulture were greatly exaggerated. The plants were ciphers, more like NFTrees than the real thing. Cryptocurrenseed, if you will. Which you shouldn't, but I did.

If the Clippers, Aspiration, and Kawhi Leonard are guilty of the alleged infractions, the team will be in big trouble. As of yet, no paper trail has emerged, which makes sense, because you need actual trees to manufacture paper. This sham endorsement, in my opinion, was the perfect crime. Not because it was immaculately executed, but because it is so fun to consider. Any time a scam is about rich people trying to trick other rich people, and nobody else loses their home or feels compelled to self-harm, that's fun to me. This is my true crime.

And, I kind of think when you own a professional sports team, it's your obligation to borderline (or actually) cheat a little bit. I am not otherwise in favor of white collar crime, but I generally make exceptions for sports chicanery. After a drink or two, I'll even defend the Houston Astros sign-stealing scandal. If you can defeat an opponent with an iPhone camera and a few slaps of a trash can, that's just going above and beyond in search of victory. (Although obviously if they had defeated the Red Sox using this method I would be ripshit about it. That just goes without saying.)

It's early September, and there's a chill in the air. The WNBA playoffs haven't started yet, and I needed an infusion of fresh basketball chaos. So thank you, Kawhi Leonard. For in your silence, you have given us all something to talk about.

PEP TALK FOR A READER

I've been getting many similar pep talk requests lately and in an interest of not offering a bunch of duplicative responses week after week, I put out a call for weird little issues, and I am extremely into the responses I got. If you have a weird little request, feel free to leave it in the comments!

I have a copy of the new Mario Kart game sitting around, but I'm afraid to play it because I worry that if I do, it will eat up time I could use doing more productive things. But I really love Mario Kart!
- Kart Monster

Anecdotally, it seems like there is a cohort of people out there who could stand to apportion less time in their schedule for video game playing. If you, as an adult, have ever chugged a bottle of Mountain Dew so you'd have a place to pee without standing up from your chair, you may be such a person. There is such a thing as Too Much Fun, to steal directly from Infinite Jest, a book I have read and enjoyed in its entirety despite the internet's broad assertion that no one does that (and also despite the dispiriting facts around the behavior of David Foster Wallace the guy). I say this without hating the player or the game, but there is an amount of indoor virtual recreation that's detrimental to the rest of your life, even just in terms of eyesight, hygiene, and posture.

While I have nothing but respect for hard line "I do not dream of labor" devotees to James Baldwin's philosophy, I also don't think he meant that we should never feel an urge to be productive. Some left-memeing social media accounts are deep in the "why am i here? I was meant to lay on a warm rock eating berries." mode, which is probably closer to true than it is to false. But even in that situation you've still got to locate a suitable rock and forage for berries. A life without wage labor doesn't mean a life without work. All that is to say, even outside of the pneumatic pressure device of capitalism, dinner needs to get made and dogs need to be walked and laundry needs to be washed. There is a point at which unlimited relaxation becomes an impediment to like...lunch.

With that lengthy preamble out of the way: If you are not the type of person to let a video game where cartoon characters have go-kart races through farms, castles, and the void of space dominate your entire schedule, it's probably nice to blow off a little steam by hucking some green shells out the side of a virtual ATV. In terms of gaming pursuits, Mario Kart is pretty wholesome and family friendly. It is not going to radicalize you politically (except in favor of the society-leveling blue shell). It's not likely to alienate your children or deplete your savings with Mario Kart unless you find a way to place high stakes bets online, which I imagine exists, but you'd have to be a true sicko to seek it out.

There is only so much productivity that is actually holistically productive. Sure, you can wake up at 4am and plank for three straight hours while sending voice to text emails to your business associates. You can meal prep a batch of frozen protein popsicles for the entire month so you never have to think about what to eat, and your jaw gains definition from all the ice pop sucking you'll be doing. But...to what end? How much efficiency do we need?

It's worth asking broadly: What are we trying to produce? If the answer is something like "shareholder value" then sure you can always be creating more of that by constructing a workday that's more work than day on the balance. But if you're trying to produce endorphins or community or straight up FUN, then it's not just benign but rather imperative that you inject a little whimsy into your days. Are your bills paid enough? Is your home tidy enough? Have you connected with your loved ones? If yes, then maybe it's time to stock up on bananas and head out on the Rainbow Road in search of a little peace of mind. Or a little bonding time with some Kart-minded friends and family.

Nobody on their deathbed ever wishes they spent more time at the office. But also nobody on their deathbed ever wishes they spent more time playing video games. Why do we focus so much on people's death bed thoughts around time management? I don't think most of the time you spend dying is used to wish you organized your calendar differently at all. Life is for living. So get busy playing Mario Kart, or get busy doing spreadsheets. The choice is yours.

PICK-ME-UP SONG OF THE WEEK:
Rilo Kiley - "A Better Son/Daughter"

On Friday night we saw Rilo Kiley's reunion tour at Pier 17, which is my favorite venue in the city I think. We watched from towards the back with a little cluster of friends and had a great time. The band sounded great. Jenny Lewis is one of our coolest and most talented living rock stars. (Her solo work is great too obviously.) It had rained early in the day, but the precipitation ended before showtime, averting the threat of a ruined Maris's Birthday excursion. The first hour of the set was excellent but the group really put their collective foot on the gas for the last half hour and ripped through a bunch of fan favorites. "Better Son/Daughter" is all about weathering ups and downs and the potential for coming out stronger on the other side of the bad times. It feels...resonant!!!! (I think I included a Rilo Kiley song recently but it's Maris's post-birthday week so we're doing it again!)

Also last week, I met music critic Grace Robins-Somerville at a lovely little fundraiser (put on by the independent magazine Antics), and she reviewed the new album by Greg Freeman for Pitchfork, which got me listening to this charming, shuffling, shambling song. It's full of barroom piano and ends with horn blurts. Right up my alley! Greg Freeman has an M.J. Lenderman type of voice with a little quaver in it. It's good stuff, in my opinion (and Grace's, which is how I found it, of course)! Bonus song this week!

COLUMBO VOICE JUST ONE MORE THING

A few years ago, my friend Amina Sutton made this really sweet short film called Beach Floaty Thingys, and you can watch it now! It's lovely! The kids in it are remarkably good!