And Sometimes I Drive A Trolley

And Sometimes I Drive A Trolley

By Chris Churchill

I do a lot of stuff. I write for this magazine. I teach improv, film, documentary and theater to kids. I teach test prep to teens. I teach communication and public speaking courses to college freshmen. And there’s more.

I stare at birds. I play with my own birds.

Sometimes, I stand outside and think. You ever tried that? It’s pretty good. Sometimes, I’ll try a new food. Try that.

Trolley Driver

Trolley Driver

But when it comes to the subject of me, the thing that seems to get most people’s attention, is my oldest stream of income. I drive a trolley and give tours. I have for over 20 years. I do know quite a bit about the history of Chicago. I’m no Geoffrey Baer but I’m not bad. I have even trained tour guides. (Only the good ones. I don’t know who trained the bad ones.) I even had WGN radio personality, Justin Kauffman, refer to me on air as “One of the most recognizable tour guides in the city.” It’s not like “best” or “most entertaining” but I’ll take it as a compliment.

In terms of the driving side of the job, in the beginning, I wasn’t sure I was going to like it, but I’ll tell you something; I love it. I love driving a bus. I like not having anyone looking over my shoulder all day. I love being able to maneuver a big vehicle in downtown traffic. It’s kind of like taking your home with you everywhere.

People ask me all the time, “How can you drive this down here every day? I could never drive down here.” And I immediately lose respect for them and their fearful little souls, then I smile and politely answer the question with the same half lie. “When you’re driving this thing, people tend to get out of your way.” Everyone laughs. (I’m kidding about that, of course. In case anyone wonders, I drive veeeerrry carefully downtown.)

And I never really had a problem with any perceived status issues. I chose for years not to dwell on the fleeting moments of classism on this job. You might imagine how people can be when they hear you’re a bus driver; assuming you must not have gotten accepted into vocational school or whatever. Or when people get on the trolley and are surprised by my above average intelligence…I get it. I’m sure I was maybe a tiny bit that way myself before I had any reason to know better.

Me with my most frequent riders.

Me with my most frequent riders.

Once, maybe 18 years ago, a teenage girl, trying to impress her friends, asked me “Is this what you wanted to be when you grew up?” I’m sure I stumbled through some version of “I do other things… but I have to pay the bills,” followed by an under-my-breath “unlike some people.” I hope she grew up and married an emotionally unavailable business man and has three kids that hate her. Maybe one will end up in jail.

There are also those annoying moments when the customer, putting on their best blue collar disguise, calls you “boss” before requesting something:

“Hey, boss, you think you could stop over at this corner, for me? I appreciate it.”

“Sure, employee. Why not?”

I never really noticed the status thing until recently. Not until I got my master’s degree and became a college professor.

There are people out there who assume I’m not that smart, just because I’m the one driving the bus. (Meanwhile, I am the one driving the bus with my CDL.) So I thought, it might be of interest to some to tell you what goes on in the head of the guy driving the trolley, you know, in the event you end up on my trolley some day.

Sometimes, when I’m bored, sitting at a stop, waiting for it to be time to leave, I jot down my thoughts. Here are some of those notes that I jotted down during a recent, unnamed shuttle shift. (Just know I sometimes drive people to very popular locations here in Chicago.)

Random reflections on a Saturday afternoon:

—Just gave some tourists from India directions to the Museums: “Walk that way about a mile then take a left at the statue of Columbus... Don’t get lost like he did.” People laughed. Then I realized that, with that one joke, in all its specific details, in particular, the fact that they were the kind of Indians that Columbus had been looking for all those years ago, I had finally corrected over 500 years of racism. Left turn signal on. Check your mirrors. Pull away from the curb.


—Thought I caught someone on my trolley flashing some white supremacy sign out the big window in back. Then I realized they were just flicking a booger.


—I’m on a schedule. I don’t have the heart to tell the occupants of this full trolley how long before I leave.


—I hope no one watching me mistakes this Monster Energy Drink for a beer.

—Customer service tip: The customer is innocent until proven guilty.


—As the well-heeled middle aged woman drops a dollar in my tip box: ”It’d be a shame if that diamond ring fell in there.”

Some riders have the need to sidle up to you, while you’re driving, in order to ask you a question. All I could think of during a recent occasion of this behavior:

”Nothing you’re asking me is top secret. Please back up and talk louder.”

Here’s an annoying recurring theme in my time driving tourists around. This exchange:

”Where you from?”


“What part?”

“Orland Park”

Makes me want to turn the wheel into a lamp post. You’re NOT from Chicago! THAT’S a suburb!

Similarly, I’ll often ask a boarding passenger where they’re from and some of them will say “Where do you think?” And then you, noticing the massive chip on their shoulder, say, “New York?” and then they feel that sense of satisfaction that comes from feeling you are the best human ever to have been born and raised somewhere.

Alternately, when I ask someone where they’re from and they are from anywhere at all in Canada, guess what they say? They say, “Canada.” Almost every single time. The world’s largest country in terms of area, and they say, “Canada.” They assume the American trolley driver will think that’s fine. I always press the issue. “Where in Canada?” (Like I’m gonna know somebody there.) They tell me. I say “Oh. Cool.” I guess I could say, “Oh I’ve never been to Yellow Knife but I hear it’s lovely this time of year,” but I don’t.

And here’s one I’m nervous to admit as I’m afraid I could lose my job:

Even though I’ve been a tour guide and a staunch advocate for this city for 20 years, even though I’ve driven for celebrities, mayors, governors, presidents and even Santa Claus — presumably because I’m the type of person they want to represent Chicago in those assignments — there is one thing that is a dead giveaway that I’m not from Chicago at all:

I reject Steve Goodman’s entire catalog as annoying and cringeworthy. 

Pull trolley to the right, put in park, turn off engine, depart trolley, close door behind myself.

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