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I Was an Uber Pirate

Confessions of an Uber driver who turned off the app and went rogue

Editor’s Note: This story was originally published on September 9, 2016.

I stood in a deep hole running an electric hammer drill. A foghorn sounded from 250 feet above at ground level letting me and all the guys around me know that 500 pounds of 4×8 wooden panel forms were headed down our way. As a crane began to lower them to us, a deep boom billowed from above. Then another boom, then another and yet another. A horrific wind suddenly filled the hole as the entire load of forms fell free from the straps that held them to the crane and rained down on us. The wood exploded into dagger sized splinters and shot out in all directions. I ran as fast as I could into a nearby tunnel and avoided injury. Unbelievably, no one else was hurt either. In the end, it was just another day in construction. But if you work long enough in construction, just another day eventually becomes a catastrophic injury — or worse.

And so, after nearly 20 years on job sites, I said, “Fuck it. I’m done. I’m never working construction again.” To make up for the loss of income, I decided to do what what everyone else does when they’re in-between jobs these days — become an Uber driver. I figured it was easy money. I was born in Chicago so it was nearly impossible for me to get lost there. I’d also worked in every neighborhood in the city during my two decades in construction. My Uber take worked out to only about $20 an hour, which was a big pay cut, but working a 50-hour week for Uber felt like working a 24-hour week in construction.

Things were pretty good at the start. There were no backstabbing co-workers, no bosses unwilling to get rid of problem workers, no drama. If someone got in and was nasty to me, I remained polite and when they got out, I left them a bad rating. And when I was having a bad day and a complaint came through — causing my rating to drop — I worked harder to be professional with my riders and my rating shot back up. Better yet, I never had to talk to anyone at Uber; I went into their tranquil offices once, for all of 15 minutes, to talk to someone about a document update.

In other words, it was never my intention to turn into a pirate. It just sort of happened. One night, I pulled up in front of a bar in Chicago’s Logan Square neighborhood and a drunk girl walked up with her phone in her hand and her Uber app open. I rolled down my window and shouted, “Anna?” She nodded and got in with two friends. I turned the ride on and drove away. A few minutes later, she asked, “Where are we going?” I stopped to show her the map to her destination on my app when my phone rang. It was Anna: “I’m in front of the bar. I don’t see you.”

I looked back at the drunk girl in my back seat. “Wait, are you Anna?” I asked.

“No, I’m Anita. I thought you said Anita. I’m sorry, I’m kind of drunk.”

I sighed, and Anna canceled the ride. I then asked Anita what she wanted to do.

“Just take us to Lakeview, I’m sorry, we’ll pay cash.”

When we got there, they paid me $15 — $10 for the fare and a $5 tip for my trouble. If the ride had gone through Uber, it would’ve been about an $8 payout, meaning I’d doubled my money.

I didn’t actively seek out cash rides, however, until Uber introduced Uber Pool and my hourly rate plummeted to 12 bucks. The app was super-glitchy and riders were constantly pissed about the crazy, long routes I needed to take to accommodate everyone in the back seat. So instead, I started to stop in front of people trying to flag down cabs. At least half of the time they got in. When they’d ask how much the ride was going to cost, I told them, “Whatever you think is fair.” They often gave me a damn good rate, and if they said a ridiculously low number, we negotiated something more realistic.

The jackpot for cash rides were after major sporting events and concerts. When the doors to the United Center, Soldier Field or Wrigley Field opened, tens of thousands of people poured out. I tried to use the Uber app, but they were mainly tourists who didn’t know north from south or where any major landmarks were. That basically meant I’d spend 20 minutes looking for them only to have them cancel the ride when I didn’t find them fast enough. So I went rogue again. No one minded. The people flooding out of the stadiums were a little drunk and extremely grateful for the ride. I made well over $100 an hour many nights after Blackhawk home playoff games. It was the easiest, quickest and most fun money I’ve ever made — and I used to sell cocaine.

Until it wasn’t.

The night everything went bad began with me looking for pirate rides outside of a nightclub. A drunk woman who was crying came up to my car window and pleaded, “Can you please just take me home?” I hit the unlock button and she got in — followed by her asshole boyfriend. I asked her where she was going, and she told me the West Side. The boyfriend cut in and said, “I put it in the app already!” before going back to talking on the phone.

“Don’t listen to him,” she told me.

I drove them to their destination as the woman dozed off and the boyfriend tried to make annoying small talk with me. When we got to their place, I asked, “Who’s gonna pay?”

“What are you talking about? I already paid through the app!” the boyfriend shouted.

“No, this wasn’t through Uber; it was a cash ride,” I responded.

They ignored me and started to get out of the car.

“Someone’s gotta pay,” I yelled as they walked across the street. I looked at the drunken woman and said, “Remember when you asked me to take you home? You have to pay me. It’s 12 bucks.”

She got a weird look on her face, and the boyfriend told her to go inside, which she did.

I turned to him and said, “Look, I’m gonna get paid, man.”

He grinned, gathered up and took a swing at me that I dodged. He swung wildly two more times before I dipped my shoulder, picked him up and slammed him on the ground. His head cracked on the sidewalk, and he briefly went unconscious. After a couple of tense moments, he sat straight up like an extra on The Walking Dead, stared ahead blankly and said in a bizarre evil clown voice, “You know what I’m gonna do? I’m gonna steal your car!” Then he added in that same strange tone, “Nah, I’m gonna do something even better — I’m gonna go into my place to get my gun and fucking shoot you!”

While he ran toward his apartment, I ran toward my car. I put it in gear, and drove away as fast as I could. For the next several blocks, I kept my eye as much on the rearview mirror as the road — looking for a maniac sprinting around the corner with his gun to kill me for giving him and his girlfriend a free ride. That’s also when the paranoia (or guilt) started to set in: Could Uber track me down? Did they spy on their drivers — even when they were off the app? Was the dude hurt? Was he going to die? Drunk people can sometimes get up and walk around and do weird stuff only to collapse a few minutes later. Would I go to jail? Would I lose my job as an Uber driver?

I drove as far south as I could, turned on the Uber app and waited for the cops to come get me. But a funny thing happened, I got a ride, and I spent the rest of the night driving around the city as though nothing had ever happened.

It did, however, effectively end my days as an Uber pirate. I started only using the app again and putting as much effort as possible into my rides. I opened doors. I stocked the back seat with water. I made calls to my Pool riders when I was close so they’d be outside. My rating shot way up, and I began to get long rides to the suburbs during rush hour. My rate shot up over $20 an hour. The money wasn’t as fun or fast as before, but it was steady and safe.

Wasn’t that why I became an Uber driver in the first place?

—As told to Josh Schollmeyer