• by Steven Rosenbaum , Featured Contributor, July 14, 2025

Remember XinXin? The Uber driver who told me his "boss" wouldn't let him return my hat, so he followed Uber's instructions and handed it to the NYPD -- in Queens?

After my story about becoming "Hatless Steve" went viral, the customer service bots disappeared. Instead, I got an email from Freddi Goldstein, Uber's senior communications manager. She used to be a City Hall spokesperson. Now she works for Uber. That career trajectory alone tells you something about how the city works.

The Blame Game Begins

Goldstein's email was polished corporate jiu-jitsu. Uber had followed the rules, she insisted. Those rules? That's the Taxi and Limousine Commission(TLC)'s fault. "TLC rules specifically require drivers to bring lost items to a police station if they can't coordinate directly with the rider," she wrote, citing Rule 80-18(b)(2). Clean narrative: The city required it, not Uber.

And about XinXin's text: "I need work, my boss not allow me stay in traffic without any rider"?

"There aren't currently any fleets operating on our platform," Goldstein explained. "Rental companies don't manage drivers or oversee the use of the Uber app."

That "boss" XinXin mentioned? According to Uber, he doesn't exist.

Except that's demonstrably false. Uber literally offers fleet management software at uber.com/us/en/earn/fleet-management/. I've reached out to Uber for comment on this contradiction. So far -- radio silence.

The Regulator Blinks

TLC Commissioner David Do got me a response from press secretary James Parziale. His answers made things murkier, not clearer. "Drivers have discretion to return property if both can agree on logistics," he said. But we had agreed: The driver had my address; I had a doorman. The hat went to the precinct closest to where the driver lived, not where I lived, was picked up, or dropped off.

And what about Uber's warning that the driver risked losing his license if he didn't bring the hat to police? "A complaint or violation does not automatically trigger a loss of license," Parziale clarified. Not exactly the hard mandate Uber described. More like: "it depends."

When I called American Lease -- the company XinXin likely worked for -- and explained why I was calling, they hung up. Immediately.

I asked TLC to clarify Uber's "no fleets" claim. "Fleet is a non-specific term," Parziale replied. Translation: We're not going to touch that.

The TLC responded to Uber's misdirection with the bureaucratic equivalent of a shrug. Rather than clarify its own rules or challenge Uber's interpretation, it retreated into legalese and qualified statements that sounded like they were written by lawyers afraid of taking a position.

The Real Story: Follow the Money

XinXin's revealing text tells you everything: "I need work, my boss not allow me stay in traffic without any rider." He drives for Uber but can't make independent decisions about his time. Someone else controls his schedule and calculated that returning lost items is bad for business.

The economics are brutal. A trip from Jamaica, Queens to Manhattan and back would cost XinXin gas, tolls, and at least two hours off the platform during peak earning time. Uber's flat $20 return fee doesn't come close to covering those costs. Meanwhile, dropping the hat at the nearest police station cost him nothing but 15 minutes.

Uber could have solved this in a dozen ways: location-based return fees, app-based tips, convenient handoff locations. Or if “driver safety” is the real concern, then a police precinct a block from my home would have been fine. Still wasting the NYPD's time, but better than Queens, which -- an hour and 20 minutes away -- crosses the line from inconvenient to impossible. Maybe for an iPhone or a Stradivarius, but not a hat. Instead, Uber designed a system that makes good customer service economically impossible, then blamed government regulations when it failed.

The Political Machine

Uber isn't just a rideshare company -- it's a political actor. Through its Uber NY PAC, the company has poured over $2.7 million into city elections, including $129,000 backing a candidate opposing Council Member Shahana Hanif, who supports driver protections. Meanwhile, Council Member Shekar Krishnan is pushing Intro 276—a bill to create a public oversight board that would review Uber's deactivations, a system many drivers say leaves them unable to earn a living without warning or recourse. When I asked TLC if Uber misrepresents its rules, it dodged: "There is no indication that either the driver or the base violated any TLC rules."

Which doesn't answer the question.

Who Gets Screwed?

Uber collected its fee, shifted blame to regulators, and moved on. The TLC gets to hide behind vague rules while Uber spends millions on political influence that makes direct confrontation inadvisable. When Uber misrepresents its regulations to the public, the TLC responds with technicalities and qualified language that avoids taking a clear position. It's regulatory capture disguised as bureaucratic caution. The car lease companies collect their fees and disappear when problems arise.

But XinXin gets screwed from every direction. He's caught between Uber's algorithm that punishes him for going off-route and the rental company's demands that he maximize platform time. He's squeezed by a $20 flat fee that doesn't cover actual costs and regulations that Uber uses as cover for their own policy choices.

When XinXin texted me that his boss wouldn't let him return my hat, he wasn't lying. He was just confused about who his real boss was. His real boss is Uber's algorithm, designed to extract maximum efficiency from every trip. And that algorithm calculated that my lost hat isn't worth the detour.

The Bigger Picture

This is platform capitalism in practice. Uber builds the infrastructure, sets the incentives, and collects the fees. It controls which rides get offered to which drivers, how much those rides pay, and what happens when something goes wrong. But when something breaks, the company points to independent contractors, government regulations, and market forces.

The result is predictable. Drivers are afraid to speak out and risk deactivation. Regulators are afraid to challenge Uber's narrative and risk a well-funded political campaign. Customers are paying 48% more than in 2019 for rides with fewer protections and less recourse when things go wrong.

It's a system that privatizes profits and socializes costs, with the NYPD as Uber's de facto lost-and-found department and drivers like XinXin caught in the middle.

Somewhere in an evidence locker at the 109th Precinct in Queens, a grey pork-pie hat sits as evidence of a system designed to avoid responsibility. I still haven't gone to get it. It's not just an hour and 10 minutes each way to Queens. I have to file a police report and wait for it to be investigated -- all to prove to the NYPD that I own a hat I forgot in a car I paid to ride in.

But it's more useful where it is, as proof that when platforms claim to be neutral, someone always gets left holding the bag. And it's never the platform.