Now, before you check your prescription (or pinch yourself), rest assured that these images are a product of advanced artificial intelligence. But come on, isn’t the idea of a Christmas Day Playpen extravaganza featuring Chicago’s most prominent figures just too wild and wonderful to pass up? Indeed, the AI-generated images are going viral—and for good reason. I mean, who can resist a scene that says “Windy City winter wonderland” more than politicians and celebrities risking hypothermia just to catch a wave in front of our gorgeous skyline?

Yes, you read that right: the iconic Chicago skyline looms majestically in the background, with the shining towers reflecting off the icy lake. If you’re wondering what motivated these fictional folks to get out there in December, it’s obviously their unwavering commitment to The Playpen, that legendary boating haven that sits just north of Navy Pier. Typically, The Playpen’s prime months involve sun-soaked, mid-June weekends when the water is slightly less frigid, and the breezes aren’t threatening to turn you into a human popsicle. But these brave (and, let’s be honest, slightly insane) AI-versions of our local leaders are apparently so dedicated, they’d do anything to keep The Playpen open 365 days a year. After all, rumor has it that if you can water ski on Lake Michigan on Christmas, you can water ski anywhere, anytime. Or at least that’s what an AI chatbot told me.

In these wonderfully absurd renderings, JB Pritzker’s Santa hat has a pom-pom the size of a basketball, while Brandon Johnson sports a bright green holiday beanie with “Chicago” emblazoned across it. Lori Lightfoot, never one to be overshadowed, takes the style competition up a notch by donning a full-on Santa coat—somehow remaining perfectly balanced as she zips past cheering boaters. Meanwhile, the Obamas, the epitome of cool, manage to strike matching poses on their skis, giving us the next best thing to a red-and-green holiday card. Word on the AI street is that Michelle is wearing a Santa-themed ear-warmer that complements Barack’s giant grin. If that doesn’t spread holiday cheer, then Oprah, poised in all her regal grandeur on a bedazzled pair of skis, certainly will.

Of course, in the background of these images, the real star of the show remains the Chicago skyline itself. The Willis (formerly Sears) Tower peers through the chilly haze, and the John Hancock Center stands tall like a festive, steel tree. Lake Shore Drive shimmers in the distance, while party boats circle around the waterskiers in a comedic swirl of confetti, eggnog, and questionable dance moves. In one truly cinematic shot, Chance the Rapper spontaneously leaps off his boat, Christmas sweater and all, into the chilly water, while R. Kelly, ankle bracelet in plain view, looks on in sheer confusion. The spectators on nearby vessels are either filming the spectacle with their smartphones or clinking champagne glasses in festive camaraderie. Only in Chicago, folks. Only in Chicago.

Naturally, the question on everyone’s mind is: Why the fuss over these particular AI images? The answer is simple—these delightful, if slightly insane, portrayals underscore just how beloved The Playpen is among Chicago’s most prominent public figures. There’s been whispered talk over the years about potential restrictions, new regulations, and even the possibility of shutting down or severely limiting partying at The Playpen. But if these year-round, Santa-hat-wearing water-skiers are any indication, our beloved floating shindig spot isn’t going anywhere. After all, if the Obamas, Oprah, and pretty much every local official can show such devotion that they’d (AI-figuratively) freeze their behinds off on December 25th, how can The Playpen possibly be in any danger of being outlawed?

We Chicagoans value a good time—and nowhere is that more evident than on the water. Whether you’re a city dweller who can’t wait for those balmy Lake Michigan nights or a suburban transplant who claims to “hate the city until someone invites you on a boat,” The Playpen unites us all. This comedic, AI-generated Christmas carnival is the perfect representation of our city’s wacky spirit, where the improbable often becomes reality (though, in this case, it’s digitally fabricated reality). But hey, the mere concept is enough to keep us dreaming of our next big splash.

As we inch closer to summer 2025, let these images serve as a wacky reminder that The Playpen is here to stay—an aquatic paradise for boat-hopping, wave-riding, and memory-making. Yes, sometimes you’ll freeze. Yes, occasionally you’ll wonder if you’ve lost your mind as you try to navigate an inflatable swan in the midst of speedboats and sea-doos. But if JB Pritzker can do it in a Santa hat on Christmas Day, we know we can handle it once the weather is more forgiving.