Shyster: ShysterBall

I’ve started a little writing project. This is the eighth installment. Here’s Part 1Here’s Part 2Here’s Part 3Here’s Part 4Here’s Part 5 , Here’s Part 6 and Here’s Part 7.

It’s the spring of 2007. I wake up at 5:30 AM. I never used to do this. I am not a morning person. But I am training myself to be one.  I just started drinking coffee at the age of 33.  I need it now. The baby wakes up by 6:30. Never any later. Sometimes earlier. It’s my job to go to him when he wakes up, and it is a personal goal to have written three blog posts by the time he starts to stir.

I scan the baseball headlines. The games don’t interest me as much as the stories around the games do.  The scandals. The human drama. The things that have enough of a connection to baseball to fit in what is nominally a baseball blog, but which have enough meat on their bones to where I can come up with an angle that justifies the exercise. There are hundreds of real baseball writers. I can’t do what they do, because no one would care. But I can maybe do something that is different enough to where anyone who chooses to read my stuff will not have wasted their time.

There aren’t many readers. Twenty. Then fifty one day. If I break 100 I am ecstatic, but I am happy with whoever shows up. Hmm. Half of today’s readers were obviously looking for something else and quickly left. That’s OK. Eventually more will show up.  Eventually they do.

They start coming in real numbers when Rob Neyer takes an interest. Does he remember that he liked what I had written for Bull five years earlier? Probably not. It wasn’t very memorable. But I write something about racial politics in baseball that ESPN might not let him get away with, and he links it approvingly.  In an ESPN chat one day he says I’m his favorite baseball blogger. The traffic really starts pouring in then. I learn quickly to say what others can’t or won’t say for whatever reason. After all, I’m using a pseudonym – Shyster – so none of this can really hurt me. I want nothing more than to justify those readers’ decision to give me their time. To keep them coming back.

By the summer I’m writing as many as six posts before the baby wakes up. Some are superficial. Some are deep. I’m learning, however, that the more you write, the more people want. It’s not always about the unique takes, it’s often about just being there and reliably updating so that readers always have something new. It’s like working overnights back at the radio station: people just want a friendly voice sometimes. If you can make them laugh, all the better. If you can make them think occasionally you’re way ahead of the game.

Soon those six posts before the baby wakes up turn into six before the baby wakes up and four at work before the day gets too busy. I’m still getting all my work done, though.  Surely this isn’t going to turn into a distraction like Bull did. I’m smarter about things now. Writing shorter takes. And unlike then, I have a family now. Real responsibilities at work. I’m on the partnership track. I’m not going to blow all of that over writing, am I?

For the past four years I had gone out for drinks with coworkers several nights a week. I do it less now. I claim that it’s because of family obligations, but it’s usually because I have things I want to write. A book I want to read. I’m drifting away from my coworkers because of this. The esprit de corps of the gang is suffering because of it. I regret this a little because I like these people, but I can’t do anything about it. Drinking and sharing legal war stories with my coworkers is important for a lot of reasons, but writing makes me happy. It’s been a while since I’ve been happy.

It’s September 2007. The head of the litigation department calls me in to his office. There is no real purpose for the conversation – he says he just wants to talk – but soon he begins talking about entropy. About how, if you don’t add energy to a given system, it declines and degenerates. A legal career is that way, he says. How if you don’t constantly work at it, everything eventually crumbles.  I know what he is telling me. I don’t listen to him at all.

It’s November 2007. I’m told that I’m not making partner this year. They just want to see one more year of solid production out of me. Which is what they said last year. They don’t know that I’m writing a baseball blog every day. But they’re not idiots either. They know my head is not in the game. They’re giving me a chance. I know as soon as they give it to me that I’m not going to take it.  In the previous seven months I’ve found something I enjoy more. I have no pretensions that it could ever be a career. I just know that, unlike everything else in my life, it brings me joy.

It’s early 2008.  I’ve dropped the pseudonym and blog under my own name. I’m not sure why. I won’t get fired simply for having a blog, but I realize that I’m pushing it.

In June the Columbus Dispatch does a small story about me in a sidebar to an article about sabermetrics. They send a photographer to my office to take my picture. I’m sitting at my desk, legal books behind me, the glow of the laptop in front of me as I toss a baseball into the air.  Some partners in the firm thought it was great. No one said it was bad. Many, however, were silent. Silence among lawyers is unusual and ominous.

Later in the summer American Lawyer does a piece about me on their blog. “Lawyers with hobbies” or something like that. I realize that I’ve made a big mistake. I told the interviewer the truth about how much time the blog consumes. Anyone can read between the lines to see my priorities are out of whack.  I hear whispers that the firm brass is not pleased.

I know I should care. I know I should worry. I don’t.  I’m getting several thousand page views a day now. I’m not making a dime, but for the first time I start to get a sense that I could make a career out of writing.  The only question is whether I can make that happen before I make a mess out of my career.

Craig Calcaterra

Craig is the author of the daily baseball (and other things) newsletter, Cup of Coffee. He writes about other things at He lives in New Albany, Ohio with his wife, two kids, and many cats.

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