• by Steven Rosenbaum , Featured Contributor, Yesterday

It's not a particularly valuable hat. A grey porkpie, worn-in. The kind you forget you're wearing until you're not. I left it in the back of an Uber.

Simple mistake. It should've been a simple fix.

Instead, it became a police case file.

The driver, XinXin, was kind enough to answer my call within minutes. "I found it," he said. "I'll drop it off." I texted him the address.

The next day, when the hat didn't arrive, I called him again. No answer. I texted him again. Then it got weird.

Uber Driver XinXin: "I do not say I not to return the item to you, this two days I have no order to city, I am living in Jamaica, it takes too long time to go to your location."

By then Uber had already charged me for the ride, and a "return item charge." But my hat was being held hostage.

Next text: Uber Driver XinXin: "Uber told me to drop the item at a police department and get a report from them, I will give them your contact information."

Wait, what?

The police.

Let that sink in.

Meanwhile Uber support told me I needed to file a police report. Because of a lost hat. They had no responsibility for the driver. He didn't work for them.

The next text from XinXin made it clear: Uber Driver XinXin: "I don't know when and where I am, I can drop off your item to your location when I close to that, or I can drop it to a police station and let them contact you, I need work, my boss not allow me stay in traffic without any rider."

My boss. Who was that? It may be a Fleet operator called Americanlease - "NYC's Largest TLC Rental & Leasing Company," but I can't be sure. The driver won't tell me who he works for, Uber won't tell me who the driver works for, and Americanlease doesn't answer emails or phone calls. So, my hat remains hostage.

And now the NYPD was involved, and not because it was stolen. Not because there was a threat. Just a piece of cloth left on the seat of a car I paid to ride in. Now I was being directed—by a global tech company with billions in valuation—to walk into an NYPD precinct and say, "Hi. I'd like to report a missing hat."

And that is where my hat now lives: in evidence lockup at the 109th Precinct in Queens.

I asked Uber: "Can you tell me the name of the driver so I can reference it in the report?" Nope. Privacy policy. They won't give me his last name. Not to me. Not to the police. Not even so I can get my own damn hat back.

And it gets dumber. If I want to retrieve it, I have to travel to Queens—an hour and 10 minutes each way—and maybe they'll give it to me if I have ID and can somehow prove it's mine. What counts as proof of hat ownership, exactly? A selfie from last week?

But the deeper absurdity here isn't the cops. It's Uber. It's the way its system is designed to feel helpful while actively avoiding responsibility.

Every layer of Uber support is a loop. Tap through the app? You get an apologetic robot. Call support? You'll be transferred from one rep to another, and every transfer means repeating your name, email, and date of birth—again. I've done it maybe 20 times in the last three days. That's not technology solving a problem. That's techno-obstructionism.

The thing is, XinXin is not an Uber Driver. He works for a Fleet, and the Fleet is invisible. And here's the kicker: the fleet company can't even talk to Uber. XinXin works for them. They lease him the car. They tell him what to do. But they're locked out of Uber's walled garden like the rest of us. So Uber tells the driver "Go to the police," tells me "File a report," and vanishes behind a curtain of policy, privacy, and prescripted non-answers.

What's really happening here is simple: Uber has built layers of code and customer service that don't solve problems—they just distribute blame and burn time. Every new system update seems less about helping people and more about making it impossible to hold anyone accountable.

And so, a hat that should've been returned in 20 minutes is now in custody, literally, at the 109th Precinct.

Uber support has emailed me, now more than 20 times. I’ve gotten emails from “Senior Support” supervisors, with names like Yamkela, Ralph, Yayan, Ella, and RJ. It's possible some of them are real people, while others are robots. Yayan thanked me for 13 years as a customer, and offered me a $10 credit. Ralph offered another $20 credit. Yamkela told me the fee to return my item—$20—wouldn't be charged. When I explained to her it HADN'T been returned, she didn't respond.

Among the lines they wrote to me: "We sincerely hope you recover it soon," and "Officer Diaferia, badge number 12236, has received the item."

You could laugh. I did—at first. But underneath the comedy is something darker. Because if this is how Uber handles a forgotten hat, what happens when the stakes are higher? When it's not a hat, but a safety issue? When a human being needs help?

What Uber has built isn't a transportation company. It's a bureaucratic firewall with GPS tracking. A service that lets you move through the world, but not reach anyone in it.

So no, I don't have my hat. But I do have a better understanding of what happens when you design tech to minimize liability instead of maximize connection.

Uber didn't lose my hat. They impounded it. Digitally. Physically. And, somehow, on purpose.

I think I thought that maybe a string of emails might result in some sort of response based on exhaustion, but what I forgot is that the relentlessly polite robot humans don't get tired. They just thank me for my patience and move on to the next unhappy rider.

I remain Hatless Steve.