Hubbard Street pulsed the beat of dance clubs and bars through open doors into the brisk night. Pretty women in high heels and heavy coats navigated the dirty remnants of snow not shoveled off the teeming sidewalk. Others waited next to ogling suits in roped lines outside the trendiest clubs. Hubbard, a narrow two-lane street of brick buildings from Chicago’s earliest days, is a tricky spot, filled with taxis and Ubers trying to avoid oblivious jaywalkers careening in a drunken search for their rides. The 2AM bars emptied, while the 4AM closers stayed open. Watchful Irish Chicago cops sat in a couple of warm squad cars at the curb, flashing a spotlight and honking at Ubers daring enough to block traffic.
The UberPOOL works like a personalized bus, the Uber app matching riders headed the same way. In the chaos of well-dressed young people leaving the clubs, I found a spot and my riders found me. A cold blast of air hit when I lowered my window to confirm I was John to a sharp African-American man. I smelled the scent of dry winter air seasoned with cooked meat; the restaurants here were mostly closed for the night, but alley dumpsters held thousands’ leftovers. The man slipped in back and I gave my typical warm hello. In a distinctive deep voice he said, “How are you?”
Three young men clamored in. Small talk ended as the three spoke among themselves. I focused on the crowded street like a pinball navigating between reckless taxis. In minutes, I was on the Ontario Street expressway extension headed for Logan Square.
Settling into highway speed on the Kennedy Expressway, something startled me in the rearview mirror. The 30ish man in the middle sat almost perpendicular, oriented toward the African-American who got in first. I recalled the black-and-white era ventriloquist Edgar Bergen and his doll Charlie McCarthy. The dumb smile on the man in the center reminded me of the Charlie McCarthy doll. They weren’t talking; the Charlie McCarthy guy had an almost non-human grin. Weird, I thought, and refocused on the freeway.
While I scanned for the Fullerton Avenue exit, the black man said, “Would you please get your hand off of my knee?”
That can’t be good, I thought.
In the rearview mirror, “Charlie” was nearly perched on the other rider, his hand propped on the man’s knee, holding that doll-like grin. Even for a 2AM Uber, that was weird.
Conflict was avoided as he retracted his hand; the other two men resumed chatting. I continued with added urgency. Minutes later, I stopped for the three white men on a side street of 19th Century frame houses now popular with hipsters. They exited; “Charlie” slammed the door and ran for the snowy sidewalk. Abruptly, he stopped and turned back.
“Wait!” He pointed at the African-American in the backseat. “I’m with him!”
The man in back said, “He is not with me.”
I pressed the door lock as Charlie slid to the front side door. “Wait!” he said. “I’m going where he’s going!” He pointed in back.
That man said, “I do not know him.”
“Charlie” pulled on the door handle. “Let me in!” He yanked over and over. Uber provides no training for this. In fact, Uber provides no training. There are a few sentences of best practices buried in the app. Yet, the system works well enough; drivers figure out how to take care of riders. If not, their customer ratings fall too low and Uber drops them. I pondered what to do. “Charlie” was too close to speed away without hurting him.
“Let me in!” he said. He leaned on my car and pounded on the window. “Let me in!” He hit it harder.
He will shatter my window, I thought. For a seven dollar fare, too.
“Let me in!” He wailed as he smacked the window. Where were his friends, I wondered. Already in their house, I presumed, and of no help.
The intensity of his pounding increased; should I risk racing my car off, possibly knocking him under? No, I could run him over.
“Let me in! I’m going where he’s going!”
The man in back was silent, probably petrified. The residential street was dead quiet other than “Charlie” as it was 2:30 on a frigid night.
I opened the window a sliver. “Charlie” stopped hitting the window.
“I’m really sorry, Sir,” I said. “But, the UberPOOL rules are that I can’t let you back in once you get out.” I made that up.
“Oh,” he said and stepped back. Only a drunk would fall for that, I thought. Luckily, he was.
With a space between him and my car, I jammed the accelerator. Wheels spun on the dank pavement as I left Charlie dumbfounded.
The ride was uneventful and nearly silent the rest of the way. I bet my rider regretted saving a couple of dollars in the UberPOOL. Daytime POOL rides tend to be fine, but late night means weirdness as you get matched with random drunks, sometimes ones who want to hop on your lap because they think they’re Charlie McCarthy and you’re Edgar Bergen.
Milwaukee Avenue 