Big Mike: Can A Barn Boss Be A Friend?

One of the ongoing motifs of this site is Benny Jay’s amazing inability to grasp many of the simplest precepts of computers and the Internet.

For a couple of weeks last year, he and I spoke day after day on the telephone, me trying to get him to understand how to open a new window on his screen. He had no idea what I was talking about. That’s like your doctor saying, You have a fever? Hmm, I don’t know anything about that. If I understand Benny correctly these days, he doesn’t yet know how to create a folder. That’s like a native English speaker admitting he doesn’t know the definition of the word the.

You and I know Benny is a supremely gifted thinker. Time and again I’ve said Benny Jay is one of the three smartest guys I’ve ever known. The other two, by the way, are Aaron Freeman, the comedian, commentator and professional contrarian, and Damien Reynolds, a one-time Jeopardy! champion and the world’s most curmudgeonly options trader/cabdriver.

Damien Reynolds (With Guitar) At Woodstock

So it’s not that Benny Jay lacks the neurons and axons to comprehend the gobbledygook that is computerese. It’s got to be something else. But what?

Before I attempt to diagnose the poor sucker I must add he’s like a dope addict, surrounding himself with shady characters also carrying monkeys on their backs. For instance, he spends a great deal of time with Milo, Gary, Indiana’s Greatest Writer. Milo, although a fine wordsmith and accomplished self-abuser, is nearly as baffled by the computer as Benny is. The other day, in my role as Barn Boss of this communications colossus, I issued a fiat demanding that all contributors categorize their posts.

That’s Me, On The Right

I figured most of us were getting just a little lazy. I know I was. Occasionally I’d slap up a post and dash off, promising myself I’ll categorize it later, knowing full well I wouldn’t keep it. Several minutes later, an email came back from Milo:

I am a dumbass. I don’t know how to categorize.

That ranks right up there with My name is Bill and I’m an alcoholic as a startling yet hopeful admission of frailty. I quickly dashed off a step-by-step tutorial on categorizing. I sent it out to all the principals of this entrepreneurial juggernaut — Benny, Milo and Jumpin’ Jonny Randolph, Chicago’s finest photojournalist. Benny Jay emailed me back moments later, writing:

This is so well done even I understand it.

I’ve yet to hear a peep from Milo. He’s probably lying in some uncategorized gutter somewhere.

Ned Ludd would be proud of the both of them.

Now and again I become peevish when talking to Benny Jay about things we have to do to maintain this national treasure of a site. A good half dozen times I’ve hung up wanting to scream, Stop being such a blockhead!

I know he senses my impatience churning beneath the surface. I feel bad about it. Benny Jay and I, friends and colleagues for more than 25 years, have never exchanged a harsh word. One of the reasons I’m drawn to him is the fact that his serenity seems to temper my rashness. Had I thrown my lot in with Milo, say, the two of us would be carousing, ingesting too many substances, breaking too many sacred vows, and otherwise pushing each other into early graves. Even though I consider Milo a prince, I have to hold him at arm’s length for my own well-being.

What Would Happen If Milo And I Were Best Friends?

Once in a while, I entertain silly thoughts. Benny Jay considers working with computers and our website beneath him. His life’s work — uncovering the petty tyranny that is the Richie Daley empire — is far too important for him to be distracted by trivialities like windows and folders. Let Big Mike, that schlub, do the dirty work. But naw, Benny Jay’s never been a jerk like that.

Then I wonder if he and Milo might be conspiring against me. Let’s act dumb all the time in front of Big Mike, they whisper to each other. Then maybe he’ll quit in frustration and we won’t have to cut him in on the big payoff when this thing goes global. No, couldn’t be. Milo might be a cut-throat but he couldn’t be delusional enough to think there’ll be a big payoff on The Third City. And as far as global ambition goes, Benny Jay’s quite satisfied that The Third City is the talk of his bowling alley.

The other day, in the midst of another of one of these paranoiac jags, I rang up Benny Jay. We chitchatted for a few minutes. Finally he blurted, You’ve been mad at me about all this computer stuff, haven’t you? It felt as though he’d knocked down the brick wall between us. Yes, yes, I cried. It was catharsis.

Calmly, patiently, Benny Jay explained his aversion to cyber-awareness. “You know how you had that trouble with bridges and trains?” he asked. (From 1985 through 1996 I suffered from melange of phobias that prevented me from leaving the house for weeks at a time, riding the el, driving on an expressway, et cetera — I was a wreck.) “What if I told you ‘Just don’t worry about that bridge’? Would that have made things any better?”

“Yabbut I was agoraphic, acrophobic, claustrophobic, suffering from panic disorder, insomniac, you name it. I’ve got the papers to prove it. My shrink wanted to nominate me for the Neurotics Hall of Fame.”

“Well, did it ever occur to you that I might be as crazy as you are?” Benny asked, his voice still even.

“Yabbut….”

“‘Yabbut’ nothing,” Benny replied. “I’m a freak.” He went on to explain how working with computers and this Third City racket have been jabbing him in all his psychological weak points — his dread of making mistakes, his unreasonable fear that he’ll wreck the whole operation with the inadvertent click of a key, his panic at confronting the new, his terror of technology. He even told me he was years behind all the other kids in learning how to tie his shoes.

It was a revelation. I’d never thought of Benny Jay as a loon. But here it was. I realized he could benefit from a cocktail of skull jockey drugs that’d make my daily dosages look like St. Joseph’s Aspirin for Children.

I feel much kindlier toward Benny Jay now that I know he’s not plotting with Milo behind my back. In my role as caring and loving friend, I hope to provide him help and support as he attempts to overcome these psychological impediments.

In my role as Barn Boss of The Third City, though, I must say, Goddamn it! Just don’t worry about that bridge!