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Shady Uber Driver Is To Steal Phone And Wallet Left In The Car, Passenger Outsmarts Him And Gets Their Things Back

by Jeffrey Stone
December 3, 2025
in Social Issues

A Redditor’s lost phone and wallet spark a wild chase when a shady Uber driver demands a $200 ransom. Reddit’s AITA cheers: was their sneaky retrieval genius or reckless?

After a late-night party, the Redditor realizes their belongings are trapped in an Uber. The driver’s $200 demand triggers a cunning downtown Chicago retrieval plot, dodging voicemails for a sly grab. The Reddit post poses desperation versus daring, with users divided on whether the Redditor’s cinematic caper was a brilliant comeback or a dangerous dance with a dodgy driver.

Redditor outsmarts a shady Uber driver holding their phone and wallet hostage, exposing gig economy trust issues.

Shady Uber Driver Is To Steal Phone And Wallet Left In The Car, Passenger Outsmarts Him And Gets Their Things Back
Not the actual photo.

'When an Uber driver refuses to return your stuff?'

First of all, I understand leaving something behind in an Uber is a pain in the a__ for the driver.

Uber has recently added a $15 fee for a driver returning an item which I completely support and in the past,

I’ve given a driver a $20 tip for returning my item. Now to my story-

Late Friday night I left both my phone and wallet in an Uber on my way home from a party.

I thought they might have been left at the party, so I waited until Saturday morning to check before reaching out to the Uber driver.

My phone is off so no luck with find my iPhone, which is strange because I went out with a full charge.

My friend is unable to find it at his place to I reach out to the driver.

I try him a few times throughout the day and I either get his voicemail or he answers and immediately hangs up.

I understand they work weird hours so no alarms yet. Finally, I get through and he confirms he has the phone, but says he can’t meet today.

When I ask when he can meet, he starts to pretend he can’t hear me and just says “Hello? Hello?” Before hanging up.

I try him the rest of Saturday and Sunday, getting the same voicemail/hang up runaround.

I reach out to Uber, who reaches out to him directly asking about my items.

Monday morning Uber tells me he doesn’t have them, and despite me telling them

that he confirmed that he did on Saturday, they were about as helpful as you’d expect.

I get ahold of the driver Monday afternoon after repeated attempts, which is only the second time I’ve ever spoken to him at this point.

His story is now that he doesn’t have them, and when I say I’m going to get the cops involved,

he hesitates for a second but then doubles down and says he can prove he doesn’t have them (?).

I file the police report and then as a last ditch effort, decide to take the number I got from his answering machine

(Uber connects you via phone rather than giving you their number) and text him, offering $200 for my items returned, no questions asked.

Well guys, as luck would have it, he found my phone and wallet! My offer must have made them magically appear out of thin air!

I grab $200 from the bank and we arrange a meeting time, which he repeatedly moves.

I’m having to do this all without a phone, so shout out to my lovely wife for coordinating this all.

He’s apparently very excited during this call, and is asking how his “reward” will be paid.

I wait in the rain for an hour for this guy, in a see of downtown Chicago Uber’s. Finally I spot his car, confirm it’s him, and jump into the...

I pull out the money and ask to see my stuff, which he pulls out of his center console and places near me.

I start counting out the money on my lap, and once I reach $200 I pick it up, take my wallet and phone and say “here you go!” without actually...

I book it out the car and don’t look back. I go the opposite way he’s facing so that he can’t follow me, and make my way to a pedestrian...

Surprise surprise, my phone is turned off with plenty of battery left, which means he turned it off so I couldn’t find it.

I feel for Uber drivers who have to deal with customers leaving stuff behind,

but I would have happily have worked with him to make it as convenient as possible to return my things.

Refusing to coordinate and then lying about having things that you find is theft, and it felt great to pull a fast one on this a__hole.

Meeting an Uber driver to retrieve your lost belongings shouldn’t feel like negotiating a hostage crisis, but for this Redditor, it was exactly that.

The story kicks off with a classic blunder: leaving a phone and wallet in an Uber after a late-night bash. What followed was a maddening game of phone tag, with the driver dodging calls, faking bad connections, and even denying he had the items, despite admitting otherwise. It’s the kind of saga that makes you want to scream into a pillow.

The Redditor’s situation highlights a murky corner of the gig economy: the power imbalance when drivers hold onto passengers’ items. On one side, drivers deal with the hassle of returning lost goods, often for minimal reward. Uber’s $15 return fee is a start, but as the Redditor noted, they’ve tipped $20 in the past for prompt returns.

On the other side, withholding items and demanding exorbitant sums, like the $200 this driver “magically” accepted, crosses into extortion territory. It’s a trust breach that leaves passengers vulnerable, especially when platforms like Uber offer limited recourse.

This issue taps into broader gig economy dynamics. A 2023 study by the Pew Research Center found that 60% of gig workers feel underpaid for their efforts, which might explain why some resort to drastic measures like holding items hostage.

Yet, this driver’s behavior, turning off the phone to disable tracking and flip-flopping on possession, suggests more than just frustration. It’s a calculated move, and it’s not uncommon.

This driver’s excitement over the “reward” payment hints at opportunism, not just compensation. As Aaron Benanav, a labor historian at the University of Chicago, explains, the gig economy “is being used to replace skilled workers with less skilled, or continuing a process that’s happening all over the world of ‘disguised employment,’ where you bring in independent contractors to replace employees”.

In the case of ride-sharing drivers, this misclassification dynamic can foster a sense of entitlement to side gains, like inflating return fees for lost items, as a way to claw back control in a system that treats workers as disposable cogs rather than valued partners.

Benanav’s perspective, rooted in global labor trends, illuminates how platforms like Uber perpetuate this “disguised employment” by offloading risks, such as fuel costs or idle time, onto drivers while reaping the profits.

The driver’s evasion tactics and sudden “discovery” of the items echo this broader exploitation, where undervalued workers might justify small rebellions against passengers to offset their own precarity. It’s a vicious cycle: platforms dodge responsibilities, drivers feel shortchanged, and passengers end up negotiating for their own belongings.

Yet, this doesn’t absolve the individual actions; it spotlights the urgent call for regulatory tweaks to redefine gig roles more equitably. Benanav’s analysis suggests that enforcing clearer employee status could deter such opportunism by providing drivers with baseline security, reducing the temptation to game the system.

Platforms might then invest in robust lost-item protocols, turning potential conflicts into seamless resolutions. For everyone involved, it’s a reminder that true flexibility in the gig world shouldn’t come at the expense of trust or fairness.

Take a look at the comments from fellow users:

Some commend OP for handling the situation and suggest reporting the driver to Uber.

mouppp − Please tell me you contacted Uber and told them all this so he is banned.

This is literally extortion and makes me wonder how many s__tty other things this guy does to his passengers

Locustsrules − You did good u/JudgeJudy1979, Uber driver had it coming for refusing to give back your phone and wallet

as well as denying that he had it when really he did have...

Aggiegirl2013 − Good job OP. But also make sure to monitor all your credit cards and any debit card that was in your wallet.

He easily could have taken pics of the cards. Might want to have them all reissued anyway just to be safe.

Others share similar experiences of unethical drivers holding items hostage.

noodleparty − Ugh I had an uber driver hold my purse with my only set of keys hostage once...

I gave him the money once he gave me my purse and he said “this is not enough” while still holding the purse.

And I said “it better be since you are essentially stealing my purse right now and there is a cop that lives next door”... What a f__k s__t.

[Reddit User] − This isn’t petty, it’s well deserved. The same thing happened to an old roommate of mine, back and forth, yes I have it, no I don’t.

When my roommate threatened with making a police report the phone also miraculously appeared (lol)...

He finally dropped it off to our house after two weeks, and left it on the ground with the screen cracked, while it was raining...

Some highlight positive experiences with drivers to contrast the bad behavior.

serenityclearwater − When I was driving for Uber a girl left her phone in my car and I just returned it without asking for the fee.

It didn’t even occur to me to charge her for a 10 minute drive.

Oshabeestie − I left a pair of gloves in an Uber in San Francisco and the Uber driver dropped them in my hotel for me and then called me.

I didn’t even notice they were missing until he called! So there are good guys out there!

KenMixtape − I drive Lyft part time. I’ve had phones left in my car nearly a dozen times... I’ve always returned them.

Rewards are nice (got $20 a few times) but don’t really expect them. I spent a few bucks mailing a phone last week.

This Redditor’s wild ride, from a lost phone and wallet to outsmarting a shady Uber driver, feels like a plot twist straight out of a thriller. Their quick thinking in that rainy Chicago showdown was a mic-drop moment, but it raises bigger questions.

Was their bait-and-switch fair, given the driver’s extortion antics, or did they risk too much for revenge? How would you handle a driver holding your stuff hostage? Would you pay up, call the cops, or pull your own sneaky move? Drop your hot takes and let’s keep this drama rolling!

Jeffrey Stone

Jeffrey Stone

Jeffrey Stone is a valuable freelance writer at DAILY HIGHLIGHT. As a senior entertainment and news writer, Jarvis brings a wealth of expertise in the field, specifically focusing on the entertainment industry.

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