Milan Update #5: Tickle Me Elmo

There are certain moments in television history that feel seismic.  The moon landing. The finale of Friends. And now, Martha Stewart finally making it to Italy.

For years, Italy has belonged to Stanley Tucci. He sipped. He simmered. He gestured meaningfully at olive oil like it was a long-lost cousin, but this week…Tucci is out. And in a plot twist no one saw coming, but secretly hoped for, Martha Stewart has arrived and joined her best friend Snoop.

That’s right. The domestic goddess and the West Coast icon have touched down like the most unexpected buddy comedy ever greenlit by the Olympics. If you thought Snoop Dogg and Martha Stewart’s appearance at the equestrian dressage event during the 2024 Paris Olympics was considered a viral success of the games, then your bar is very low because Martha and Snoop had Date Night in the heart of Milan and if you watched last night, I’m almost certain you would agree.

It started innocently enough. A small dinner at a lovely high-end restaurant in Milan. Now when Italians say small dinner, they really mean Amuse-bouche, Antipasti, Pasta, and another pasta just to compare. Fish, Meat, Salad, Cheese, Dessert, Espresso, Digestivo and a 40-minute discussion about olive oil viscosity. Three and a half hours later, Snoop is checking his watch like he’s about to miss a flight because they have opera tickets at the famous theater La Scala. Somewhere between the second espresso and the sommelier explaining soil composition, someone whispers, “We’re going to miss the overture.”

They arrive at La Scala just shy of disaster. The chandeliers glow. The orchestra tunes. The crowd turns. Somewhere in the upper tier, a patron whispers, “Is that…?” Yes. It is. Martha Stewart and Snoop Dogg, sliding into their seats like the most unexpected opera subplot ever written.

And after opera, after the endless dinner, Martha and Snoop stroll into the NBC compound around midnight. No velvet ropes. No chandeliers. Just fluorescent lighting and exhausted crew members. They’re holding gelato from the commissary. Martha is evaluating the pistachio texture like she’s judging an international dairy summit. Snoop is recounting La Scala like it was a halftime show.  And I must admit, there is something deeply humbling about watching Martha Stewart stand under fluorescent lighting holding a paper cup of pistachio. Because that’s the Olympics in a nutshell. It strips away elitism. It strips away polish. It strips away the illusion that anyone, celebrity, superstar, legend is immune from very human moments.

Which brings me to Mikaela Shiffrin.

At the 2022 Winter Olympics, she experienced what athletes call the yips…that cruel mental block where your brain suddenly forgets how to do the thing you’ve done flawlessly your entire life. She couldn’t finish her races. Slalom? Out. Giant slalom? Out. Combined? Out. At least she was consistent. It was the most heartbreaking kind of deja vu. 

Every time she approached a gate, the collective global audience held its breath… and then exhaled into a snowbank. And because the Olympics are emotionally chaotic, the narrative machine did what it always does…overanalyzed, overreacted, over-everythinged.

Fast forward.

Now…She finishes slalom with gold. And suddenly her phone is lighting up like a sponsor reunion tour.

“Hey Mikaela! Just checking in!”

“We always believed in you!”

“Remember that yogurt commercial idea?”

Amazing how confidence returns at the same speed as medal counts.

Gold after public unraveling…that’s impressive and resilient. It’s easy to celebrate dominance. It’s much harder and much more powerful to celebrate recovery. One minute you’re skiing out and the entire planet is dissecting your mental state. The next, you’re finishing strong, medal around your neck, and again, every sponsor that just wanted to give you space is calling back like a long-lost cousin.

The Olympics compress life like that. Opera almost missed, legends momentarily human and global icons balancing melting gelato with plastic spoons. Under fluorescent lights, titles dissolve. Everyone is just someone who showed up and that’s the point. Whether you’re Martha evaluating texture, Snoop rewriting cultural diplomacy one story at a time, or Shiffrin reclaiming a finish line, the games bring you back to the same truth. Greatness isn’t the absence of struggle. It’s the courage to step back into the arena. Even if you’re doing it in NBC lighting.

Lastly, let’s talk about the Olympic pin trade. It’s a tradition that somehow turns grown adults into treasure-hunting, handshake-negotiating children. Tokyo and Beijing put a damper on it thanks to COVID; no crowded halls, no frantic early-morning trades, but Paris and now Milan are making up for lost time.

And the stakes are higher than ever. Snoop has his own pin, naturally, which means everyone else thinks they can do the same. Even Simone Biles brought her Team USA goat pin to the speedskating and hockey events, because why wouldn’t she? Meanwhile, Sesame Street is in on the action, showcasing Cookie Monster, Elmo, and Big Bird like they’re negotiating for gold. In fact, Sesame Street filmed on set at the NBC compound, where Elmo and friends hung out with Team USA athletes. As a parting gift, they left a bowl of pins and it was like throwing chum into shark-infested waters. Grown men and women sprinted and shoved each other aside like their lives depended on it, all for a tiny metal rectangle featuring a smiling monster.

The bar has been raised but also equalized. Suddenly, normal day mignons in the NBC compound from on-camera talent to cinematographers, even the person behind the gelato cart are making their own pins. You’ve got tiny cameras with googly eyes for the cinematographers, miniature microphones for the reporters, a gelato cone with a little smile for the commissary crew, and even a broom crossed with an eSIM card for the logistics crew. It’s like a miniature Olympic universe on enamel, and everyone’s trying to stake their claim.

As for me…I’m a retired athlete. No viral moves, no social media skills, no Snoop-level swag. If I made a personal pin, it wouldn’t feature a finish line or highlight reel. It would celebrate what I do best which is savoring a nice bottle of wine from Italy’s finest Piedmont region. Honestly… maybe that deserves a pin too. At the very least, it would be the only pin where “expert in enjoying life” is an official Olympic event.

Who knows a printing facility I can call?

More to come….