Commentary

My Uber Saga: When A Hat Is More Than A Hat

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.

2 comments about "My Uber Saga: When A Hat Is More Than A Hat".

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Steve Rosenbaum from SustainableMedia.Center, July 23, 2025 at 3:46 p.m.
Uber responded - see what you think:

Part 1 -
Steven,

I suggest you refer back to my original email. I said clearly that “TLC rules specifically require drivers to bring lost items to a police station if they can't coordinate directly with the rider (Rule 80-18(b)(2)).” The TLC confirmed the same. If a driver and rider can’t successfully coordinate an exchange, the driver is required to bring the item to an NYPD precinct. I also linked you directly (and am providing it again above) to where you can find this information yourself online. What I shared is consistent with what James told you and what you can read for yourself on the TLC’s site.

Again, many of these questions have been answered in my prior emails.

XinXin is his own boss. Drivers on our platform are independent contractors. They can choose to accept trips or reject trips entirely at will. There is no requirement that they work set days, a minimum number of hours, or that they accept a minimum percentage of trip offers in order to stay on our platform. They can work for three weeks a year and reject 95% of trip requests and remain eligible to work on our platform.

Uber is a technology platform that connects drivers with ride requests. We price trips, dispatch offers to drivers on our platform and pay drivers in accordance with TLC regulations. As you can see online, drivers are paid for the time they spend with a passenger in the vehicle. As such, it is entirely up to a driver whether they feel it’s worth their time to return an item, or if it’s more cost efficient to bring the item to a local precinct for the item’s owner to pick up. We attempt to incentivize the former by paying the driver for the trip and, in your case, attempt to make it easier for the rider to pick up the item if it’s dropped at a precinct by providing ride credits so you can get it at no cost to you.

As is our policy, when the lost item was reported, we got in touch with the driver to attempt to facilitate a return of your hat. When the driver was unable to return your item with you directly, we suggested he drop it at a local precinct - as is both the TLC’s requirement and our policy. I understand the precinct in Queens (or as you call it, “out of town”) is inconvenient for you and I understand your frustration. On the flip side, bringing the hat to a precinct in Manhattan was inconvenient for your driver. Out of consideration for his time, as well, drivers are not required to drop it off at a precinct closest to you or directly with your doorman.
Reply

Steve Rosenbaum from SustainableMedia.Center, July 23, 2025 at 3:47 p.m.

Part 2

I cannot speak to what was relayed to you by the driver over text. What I can say with certainty is that Uber did not prevent the return of your hat and does not tell drivers that we don't allow the return of lost items - this should be obvious considering we actually pay for their return. Reading between the lines, my best guess is that the driver blamed an amorphous “boss” to end the conversation.

In reference to Intro 276, where you say Lyft has commented and Uber has not, I think you may be confusing the companies. Uber testified in person in front of the City Council at the hearing for the bill in September and submitted a written comment to the Council. Please make sure you have this reported accurately.

There are many things factually inaccurate with the paragraph you shared. Should you feel like correcting any of them, here you go:
Drivers on our platform are independent.
It is not accurate to say “the base is the only entity legally allowed to dispatch trips.” Trips can be dispatched to vehicles by bases other than the base their vehicle is affiliated with. For example, if a driver affiliates their vehicle with Uber, Lyft can still dispatch rides to that driver. In New York City, pursuant to TLC's rules, vehicles (not drivers) are affiliated with licensed bases (here, XinXin affiliated his vehicle with Uber's base) and those bases must dispatch the vehicle for a prearranged trip. TLC rules permit other bases to dispatch a vehicle as long as the consumer is made aware of the dispatching and affiliated base. This is why you see 'dispatched by' and 'affiliated with' on your receipts.
Uber does not “assign” trips. Assign implies that we tell a driver they must do a certain trip. That is not how it works. We send trip offers to drivers simultaneously for them to accept or reject. There is no requirement to accept any number of trips.
The TLC sets the minimum pay requirement for drivers in New York City. Uber complies with that law. Drivers are told what they will make on each trip (exclusive of tips) and the time and distance to both the pick up and drop off when they receive a trip offer. They then determine whether the pay for that specific trip is worth their time and accept or reject the offer.
Drivers are held to Uber’s Community Guidelines, just like riders are. If a driver violates those guidelines, for example, is reported to have driven dangerously, or to have harassed a rider, they risk losing access to the platform. Except in extreme cases that pose a significant safety risk, drivers are given several warnings and the opportunity to improve before losing access to the app. Uber also removes drivers from the app at the directive of the TLC, the licensing agent.

I hope this helps finally clear up any outstanding misconceptions.

Thank you,
Freddi