Becoming a City Slicker, Dawg

When I visit Chicago, a constant track plays through my head. It’s my voice, only a little gruffer, and it sounds like this:

That’s right, suckas, I belong here. I’m a city man just like all of you. See this swagger? I ain’t messin’ ‘round, boys. I may look like I shop at Gap, but this shirt is actually from Goodwill. And it’s concealing a giant tattoo. Of a dragon. Coiled around a switchblade. Yo.

I prepare for a trip to Chicago as if rehearsing lines for a school play—an apt metaphor, since I’m no more convincing in my role than the preppy theater kids you knew in high school.

On a recent trip, I exited the plane at Midway, the more ghetto of the two Chicago airports, right around midnight. I was to take the orange line train from Midway to a downtown transfer, taking the blue line to Logan Square. Explaining this to friends back home, I made it sound as if I were Frodo entering Mordor, only a taller, manlier version—with less foot hair.

To be fair, the situation actually was a bit sketchy. 2012 has been one of the worst years for shootings in Chicago in a long while. And although Logan Square isn’t the worst neighborhood in Chicago, it also isn’t, well… Colorado Springs.

I belong here, fools, I thought as I made my way down a long, dark tunnel to the orange line. I was raised in a dumpster and breast fed on city smog.

I purchased a train pass and tried to feed it into the turnstile. (You know those rotating tri-bar thingies you have to push through to board a rollercoaster? They have a name!) I kept changing the orientation of the card, people passing expertly through other turnstiles as I stood there fiddling. My plight was so obvious that finally a big black lady (there’s black people in Chicago!) came up to me, turned my card vertical instead of horizontal, and fed it through.

“Thanks,” I said.

No prob. I’m still cool. I drink my frappuccinos without whipped cream, dawg! I eat my yogurt with a fork! So dang cool.

My carry-on suddenly caught in the teeth of the turnstile, jamming. I worked at it frantically, jiggling the turnstile, which was now locked. I could feel the eyes of every gangster in Chicago on me, because, as you know, they all hang out at the Midway airport. (Conducting research this morning, I asked my mom what you would call a person in the inner city who was up to no good. She pondered the question and said, “A scoundrel… Or some word that starts with a ‘V.’”)

Finally, I worked the handle loose and lofted my suitcase over.

C-O-O-L, cooool.

Before going to Chicago, my cousin Chris warned me that there have been a lot of flash mobs this year.

"Awesome!" I said, imagining spontaneous musicals surrounding me like I've seen on youtube. "I've actually always wanted to be a part of a flash mob."

He stared at me as if thinking, You can't really be this dumb. Oh yes, Chris, I can.

He said, "Flash mobs are where people suddenly gang up on you, assault you, and steal your money."

Oh. Right... Are you sure there's no singing involved?

The next day, I took the blue line to a greenhouse just outside of Chicago. I was a pro now, no more fumbling with the train pass, no more carry-on. The train was packed with potential muggers and hoodlums, but I had enough street smarts to shift my backpack in front of me.

Ha! Thought I was an easy target, did you? Well guess what? I was raised in the hood. And although I look like I’ve never heard of “Fiddy Cent,” (as the gangbangers say) I actually listen to rap music every day! On my boombox, in fact. Yes, fools, I am what the local thugs refer to as a “dangerous specimen.” My street name is Cosprings.

After being at the greenhouse for half an hour, I felt my back pocket, and my wallet was gone. I’d been stolen from! (Later, a friend would mock my use of the phrase “stolen from.” Not “pick pocketed?” Or even “robbed?”)

Had I put my wallet in my backpack? No. Was my wallet in a different pocket? No, I distinctly remembered having it in my back pocket when I was on the train. There could only be one conclusion: some worthlah thug had ganked me some shady biznat (thank you, urbandictionary.com).

I berated myself for my earlier decision to move my backpack to the front. If only I had kept it in the back, it would have protected my wallet. How could I have been so stupid? I began to doubt whether I could ever show my face in the city again. I was an object of ridicule, unfit to ride the blue line…

“Josh?” I heard a voice call behind me. “Josh Skaggs?”

I turned and saw two young ladies, one of them holding my wallet.

“Did you lose this?”

“Yes!” I hurried over. “Where did you find it?”

“We found it on the twirly slide.”

Of course! The greenhouse happened to have a nice twirly slide, which I would have been a fool to pass up. (And a fool not to, apparently.) Not only had I taken advantage of this attraction, but I had done so upside down.

I received my wallet with a head bowed in shame and beaming red cheeks.

Three days later, returning to Midway and good ol’ Colorado Springs, I had recovered enough from my shame to resume the inner monologue, mentally talking smack as I walked the streets.

I ain’t lookin’ for trouble, but if trouble should find me, be warned—I got a piece, and I know how to use it. I could pump yo chest fulla lead, homeboy! Thas right. J Wack in the hizzouse!

My carry-on snagged on a crack in the sidewalk, and I almost dropped the ice cream cone I had been licking.