IN DEFENSE OF QUESADILLA POSTERS.
The only ad newsletter that chooses not to be mad about fun.
It’s Saturday. I’ve finished a few hours of social media for a client, and I’m in various conversations about sports with some of our team. Its not lost on me that when you’re working on sports, you’re always working and talking about sports. I don’t hate it.
The night before Toronto Blue Kazuma Okamoto went deep twice against the Twins. He just misses a third.
Through interpreter Yusuke Oshima, he delivers one of the great post-game lines of the year:
“I didn’t have my pre-game quesadilla today. I think if I’d had that, it would have been a home run.”
Beat writers ate it up. MLB ran with it. The Jays followed the next day with “We think he had his quesadilla today” when he blasted another homer.
I had shifted to my own feed vs. our client’s feed. Having the kind of Saturday-morning fun social media used to be made for. One member of our team was commenting on something that showed up in my feed about the Quesadilla that launched a thousand likes.
It hit me that this was the perfect 80s sports poster idea.
The Quesadilla. Quesadilla Power. Quesadillas in the Outfield. This is exactly how the great 80s sports posters were born. Before there were memes. Or even social media. A pun or a little joke became a poster of epic proportion. It maybe even became a hat.
It was just pure stupid fun. Except out of a few hundred likes across a few versions and posts, two people replied “AI slop 👎.” That made me laugh out loud.
Didn’t they know this AI-made poster was pure nostalgia?
I didn’t think this through in the moment. But the aesthetic I was reaching for has a name.
In 1984, two Greek brothers in Seattle started a t-shirt company out of their dad’s parking garage. John and Tock Costacos. Their first hit was a Huskies shirt called “Purple Reign” — Prince crossed with the Washington defense. If you grew up in the Pacific Northwest you knew this shirt.
Two years later they noticed nobody was making decent sports posters. They went after Seahawks safety Kenny Easley. Cast him as “The Enforcer.” They couldn’t get a league license so they couldn’t show team uniforms. So they leaned entirely on Easley’s persona instead. That accident made them.
By 1996 they’d sold 30 million posters. Bash Brothers — Canseco and McGwire posed on the hood of an Oakland PD cruiser with giant Louisville Sluggers. Rickey Henderson as the Man of Steal. Bo Jackson was “Black & Blue.” Lawrence Taylor ended up as the Terminator. Jim McMahon as Mad Mac, a play on Mad Max.
There was the epic Andre Dawson as the Hawk. An incredible Kirk Gibson Big Game Hunter poster. And of course my favourite player, Will Clark, in an incredible Pacific Sock Exchange classic with Kevin Mitchell.
These weren’t team-approved corporate marketing. The leagues hated them at first. The athletes loved them.
Then a thing happened. The Costacos brothers eventually got their league licenses. They could finally put guys in real uniforms. The work got worse. The sanctioned stuff lacked the gonzo creativity of the bootleg years.
Today these posters hang in galleries next to Jeff Koons. Dana White paid $2,500 each for them at a New York show.
The official book of their work, Walls of Fame features the definative quote from Charles Barkley:
“The poster made you cool. You didn’t make the poster cool.”
The Quesadilla poster I made with AI is a Costacos Brothers poster with 2026 tools and 50 fewer dollars worth of explosives.
On X it was clearly labeled as AI.
I wasn’t passing it off as not AI. It was the equivalent of me dropping a Michael Scott The Office GIF.
The problem was more about fun.
The Carolina Hurricanes sold 4,687 Beer Skates Friday night at the Lenovo Center. One in every four fans. A plastic ice skate that holds a beer. Introduced with a ten-second pour clip and the line “BEER SKATES ARE HERE 🚨.” The real question is how have we lived without beer skates all this time?
The next morning they posted a follow-up — “Can confirm Beer Skates were a hit” — over a stat card with the sales number and three fans clutching three skates apiece.
While other franchises pump out gameday graphic templates, they’re just putting beer in a skate and posting that.
Carolina’s mascot Stormy is currently in a one-sided beef with Gritty. Gritty posted “rd 2.” Stormy quoted it: “Welcome to hell you muppet reject.” That’s good copy. From a costumed dog.
What’s striking: the league offices aren’t driving any of this.
Gary Bettman didn’t sign off on Beer Skates. Rob Manfred didn’t approve a whole Quesadilla content arc for Okomoto. Teams and fans have just figured out that fun is a competitive advantage. The franchises that allow themselves to invest in it are eating the ones that won’t.
Same lesson the Costacos brothers learned the hard way. The closer you are to the core, ruins it. Fun comes from somebody not asking permission.
But here’s where it gets un-fun.
On Saturday May 3rd, the Detroit Pistons — facing elimination from the Magic in Round 1 — posted an AI graphic for Game 7. A wolf paw scratching at a magicians hat. The caption: “All Dawg.” And note the clearly labeled “Made with AI.” The playing cards are the bigger tell.
4M views. 4.7K likes.
The very next day, the Minnesota Timberwolves posted a snarky response.
1.8M views. 83K likes.
Read that ratio. The Pistons got over twice the views with a full graphic. The Wolves got seventeen times the likes with one sentence about AI.
Jack Appleby called it out: “Presenting your brand as ‘anti-AI’ really does work in 2026, when regular ol’ humans feel very threatened by technology.”
This complicates everything I’ve said up to now. So I’ll be honest about it.
The bland brigade has found a play. “Anti-AI” is now a brand stance that gets engagement. Performing a virtue is, suddenly, a content strategy. The Wolves found a market in fear and they cashed in.
And it is true, billion dollar sports teams can afford a lot of designers and can even paying for artists. That’s a lot different than me posting AI as form of a reply or comment to communicate. An art form all its own.
But.
The Wolves didn’t post a piece of art. They posted a one-liner about themselves. Eight months from now nobody will remember it. The Bash Brothers poster, the Beer Skate, even my stupid little Quesadilla poster and hat will all still be fun.
The Wolves played the algorithm. The Pistons probably aren’t losing sleep about it.
Sports is supposed to be fun.
The bland brigade is loud. Sometimes, like the Wolves last weekend, they get the algorithm to back them up.
Performing a virtue is way easier than putting beer in a skate.
But over time? They don’t win. They’ve never won. They didn’t win when teams stopped giving away calendars. They don’t win when you have to line up 4 hours early and not get a free hockey jersey for Ernie Clement. They don’t win if they don’t want me to AI myself into a Rogers ad with Ernie Clement. They won’t win the AI fight either.
They’ll just keep yelling slop at a feed that’s having more fun without them and posting “btw, none of our graphics are AI” while the Hurricanes sell 4,687 Beer Skates.
Let people put beer in a skate. Let people post an AI-made Quesadilla sports poster. Let mascots talk shit. Hell, let sports franchises post a sloppy AI photo every once in a while.
Remember. The poster makes you cool. You don’t make the poster cool.
Tools are tools. Fun is fun. Trying is trying. AI isn’t the problem.
COCKTAIL OF THE WEEK: THE PAINKILLER
The Painkiller was invented in 1971 at the Soggy Dollar Bar on Jost Van Dyke in the British Virgin Islands. The bar’s named for the fact that there’s no dock — to get there, you jump off your boat and swim to shore. By the time you’re paying, the dollars in your pocket are wet.
Cut to 1979. A guy named Charles Tobias buys the rights to a defunct British Royal Navy rum recipe and starts a brand called Pusser’s. He wants the Painkiller for his rum. He goes to the Soggy Dollar and asks for the recipe. They say no.
So in 1989 he just trademarks it.
Pusser’s filed a U.S. trademark on the name and the recipe of a drink they didn’t invent and didn’t sell. Then in 2011 they sued a tiki bar on the Lower East Side called Painkiller. The bar was forced to change its name to PKNY, hand over its website and stop calling its own drink a Painkiller unless they used Pusser’s rum.
Bartenders organized a boycott. Two Facebook groups sprang up. Pusser’s didn’t budge.
The trademark stands today. Order a Painkiller anywhere in America and the legally correct version requires the rum of the company that didn’t make the drink, didn’t name it and tried to sue the people who did.
The Soggy Dollar still serves theirs with Cruzan. Fly to Jost Van Dyke. Jump off the boat. Swim to shore. Pay with wet money. That’s the original. You can also fire up the webcam and imagine yourself there.
The Soggy Dollar version:
2 oz dark rum (Cruzan, or whatever you’ve got that’s not Pusser’s)
4 oz pineapple juice
1 oz orange juice
1 oz cream of coconut
Shake hard with ice. Pour over crushed ice in a tall glass. Grate fresh nutmeg on top. Generously. The nutmeg is non-negotiable.
Garnish with an orange slice or a pineapple wedge. Have fun.
The Drink Cart is a newsletter version of sitting at a really good bar with someone who thinks too much about advertising and won’t shut up about it. Subscribe to get it on Wednesdays and Fridays.