Every day, someone stops me on the street to say, “Hey, you’re Dennis O’Toole! You’re a lot shorter than I imagined. Still, I wish I was you. The money, the babes, the helicopter…How do I get an occasional piece on WBEZ?” Each time I’m asked, I lower my shades and say the same thing:
“You gotta pay to play.”

Being an occasional contributor to Eight Forty-Eight comes with certain privileges. I get the best tables at the finest Viagra Triangle restaurants. When I go to a sporting event, my seats get comped— courtside, skybox, or someplace safely removed from the riff-raff.  The finest prep schools in Chicago, both Catholic and atheist, beg me to send my kids there.  And I don’t even have kids…that I acknowledge.

Did talent get me this charmed life? Pfff! You should see my rough drafts. A team of English majors is required to clean up my grammar and make a modicum of sense out of my jingoistic rants. Then when I record, the finished essays have to be printed with phonetic spelling to overcome what people call my “semi-literacy.” Finally, a producer has to sit through dozens of botched takes before my least incompetent read is deemed worthy of airtime.

So no, I don’t deserve this position. I got this gig— and my Trump Tower condo—the Illinois way.  I paid to play.

My first essay aired in February, 2006. It was about sponges and how I don’t understand them. Before I set pen to paper, I handed a check in the amount of $25,000 to an old friend from my boyhood in Syria, Antoin “Tony” Rezko. Rezko then mentioned me to Antoin “Tory” Malatia, the General Manager at WBEZ, while the two were powerlifting at the East Bank Club. Tony told Tory that a guy named D.O.T. wanted to play ball.  Not a bright guy. Not an eloquent guy. In fact, a guy who can’t even legally operate a toaster. He may not know a lot, Tony said, but he knows how to fill out a check with plenty of zeroes.

WBEZ cashed the check and ran my piece. I keep writing checks, WBEZ keeps airing my nonsense. For this piece, I made sure a certain Eight Forty-Eight host—let’s call him Ricky Platinum—got that cigarette boat he’s always wanted. When I submitted this essay, it was written in ketchup on a paper towel. When I came in to record, I got stuck in a closet for over an hour. Then I spilled Cognac all over the mixing board.

But none of that matters. What matters is Melba Lara might have union trouble if this doesn’t air. Therefore, it will.