How Uber Connect Became a Delivery Service for the Underworld

The Dark Side of Rideshare

Rideshare services like Uber have revolutionized transportation, but they've also opened the door to some unexpected—and often troubling—uses. One of the most concerning developments is the rise of Uber Connect, which has essentially become a new way for drug dealers and scammers to transport illegal substances and money while leaving drivers unknowingly breaking the law.

The Evolution of Rideshare Deliveries

Before Uber rolled out Uber Connect, the concept of delivery was primarily limited to food through platforms like Uber Eats. I remember well when I first started driving for Uber in 2017. Back then, it wasn't uncommon for passengers to ask me to deliver food or packages using UberX, which was against the rules. I found it strange, but I chalked it up to the chaos of late-night college town life.

With the pandemic, Uber shifted gears to allow for package deliveries through Uber Eats, which was a temporary solution to a growing demand. For example, I remember delivering packages for an HVAC company a few mornings each week. The rates were the same as an UberX fare but without a passenger—which was a nice break from constantly driving people around. However, the launch of Uber Connect was meant to legitimize the transport of anything other than food. Unfortunately, it seems to have backfired.

My First Experience with Unconventional Deliveries

One evening in the bustling college town of West Chester, PA, I found myself delivering Indian food with UberX—long before Uber Eats made its debut in my market. As I pulled up to pick up my passenger, he approached my vehicle and asked if I could wait 5 to 10 minutes because his food wasn’t ready yet.

To say I was annoyed would be an understatement, especially since there was a 3x surge happening at that moment. Back then, Uber used to implement a surge multiplier rather than the flat dollar surge system we see today. I told him I could wait for five minutes, but after that, I’d have to cancel the trip in the app.

This was also in the days before drivers received compensation for canceled trips, and being a newbie to rideshare, I was a bit naive—I just wanted to be accommodating. Little did I know, the night was about to take an unexpected turn!

After thanking me for waiting, my passenger dashed back inside the Indian restaurant. I figured he was just picking up takeout after a night out and needed an Uber to get home. Imagine my surprise when he returned with three separate takeout bags! It turned out he was actually the owner of the restaurant and had ordered an UberX to deliver food to his customers.

I wasn’t thrilled about the situation, and I’m sure my face showed it. Sensing my frustration, he quickly handed me a $20 bill and asked, “Does this make it better?” I replied, “Sure, I got you,” feeling a bit more at ease thanks to the cash. But I was still annoyed; this detour effectively ended my night of potential surge pickups in West Chester.

Back in 2017, life as a rideshare driver was a different game. There were no upfront fares, no detailed drop-off information, and we couldn’t cancel trips and get paid. I often had no idea where I was headed or if there would be multiple stops along the way.

In this case, the trip was connected to a surge multiplier, and the restaurant owner handed me a slip with all the delivery addresses, urging me to "do what I gotta do" to get the food delivered. I could have easily dropped off the first order and called it a night, potentially scoring some free food in the process.

However, being the honest driver I am, I went ahead and completed all three deliveries as promised. With that surge multiplier attached, I decided to take the scenic route to each stop and kept the meter running for several miles after the last delivery.

Back then, I could keep the trip open and the meter running without raising any eyebrows with Uber. It was feast of famine back then, but oh how I miss those simpler times!

Was I Unknowingly Transporting Something Illegal?

Another memorable experience was when I picked up a seemingly innocent vanilla envelope from a lavish mansion in King of Prussia, PA. They were Russians and they had a driveway full of newly, expensive luxury European vehicles. 

One morning, I received a trip request from an affluent area in King of Prussia, several miles away. I had started my day about 40 minutes away in Wilmington, Delaware, but with each completed trip, I found myself inching closer to my destination in Pennsylvania.

Eventually I accepted a 45+ minute trip that was unknowingly headed to University City in Philadelphia. Back in the spring of 2018, driving for Uber was quite lucrative, especially in Philly, compared to the current rideshare landscape. It was an exciting time, and I was eager to make the most of it!

As I approached the pickup location on a secluded back road in the affluent hills of King of Prussia, I slowed down and turned into a gated driveway. After pressing the buzzer, the gate lifted, granting me access to a world of luxury.

Driving further in, an immaculate mansion emerged from behind the trees—truly a sight to behold. It felt like something straight out of Los Angeles, not Pennsylvania! The driveway was lined with expensive European cars, and the massive estate overlooked the stunning Valley Forge valley, perched majestically atop the hill.

I had no idea what was inside that vanilla envelope, and honestly, I felt pretty uncomfortable with the whole situation. I just wanted to get out of there as quickly as possible. So, I agreed to the delivery and awkwardly executed what felt like a 20-point turn in the congested driveway.

When the gate finally lifted, I felt a mix of relief and uncertainty about what awaited me at the drop-off location. A quick search on Google Maps revealed that it was a medical university, which eased my mind a bit—it was a public place, after all.

I made my way to University City in Philadelphia, where I ultimately delivered the envelope to a medical student at one of the universities there.

When I arrived at the corner in University City, the streets were bustling with hundreds of students heading to and from class. I found a parking spot, pulled in, and immediately dialed the number I’d been given. A college student on the corner picked up and started scanning for my Honda Accord. We waved at each other, and after a quick call, he hung up and walked over.

He seemed a bit annoyed and rushed, likely running late for class. As he approached, I rolled down my passenger window and greeted him politely.

“Here you go,” I said, handing him the envelope. At first, he didn’t say anything—he just grabbed it, opened it slightly to glance at the contents, then stuffed it back in and looked at me with a quick “thank you” before slipping it into his backpack.

I couldn’t help but have a few questions about that encounter!

  • Did this medical student pay the guy from the mansion to write his paper?

  • How does someone get that rich from writing college papers?

It’s interesting to think about how people used Uber to ship packages this way. What a time it was to be a rideshare driver!

The New Normal with Uber Connect

Fast forward to today, and Uber Connect has become a common way for people to ship various items. However, itAs I parked and took in the stunning scenery, a man emerged from the front door, holding a vanilla envelope and signaling for me to roll down my window.

“Here you go,” he said, handing me the envelope. “Please take this to the drop-off location; someone will be waiting for it.” He then handed me another piece of paper with a number on it, instructing me to call when I arrived.

“Wait, so you’re not coming with me?” I asked, a bit confused.

“No, just go to the drop-off location. Someone will be waiting for you,” he replied, his tone direct and almost unsettling. I couldn’t shake the feeling that this delivery was anything but ordinary! appears that this service has inadvertently facilitated illegal activities. Drivers are left in a tough spot, often unaware of what they’re transporting, and the platform seems to be struggling to enforce its rules properly.

The rideshare industry comes a host of challenges and ethical dilemmas. As drivers, we may find ourselves caught in the crossfire, navigating the fine line between legitimate work and illegal activities. Uber Connect was designed to streamline deliveries, but it seems to have created a loophole for those seeking to exploit the system.

Chuck Driver | Gig-Worker | YouTuber | Blogger

Follow me on my journey as I share my rideshare and delivery experiences with you!

https://youtube.com/@thechuckdriver
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