Why Craig Calcaterra Writes

Last week, I introduced to the wide readership a line of inquiry down which the very famous Jonah Keri had gotten me started. The line of inquiry concerns those bloggers who, despite almost no promise of financial compensation or notoriety, have persisted in their craft.

The question I posed — after having considered Will Leitch’s suggestion from his Costas Now episode that blogging is a really hard work — the question I posed goes like this:

Why do it? If, as Leitch suggests, it’s hard work, why do it? If, as I can tell you personally, it provides very little in the way of fame and/or cash money, why do it?

I’ve posed this same series of questions — or at least ones very similar to them — to some of the interweb’s more thoughtful baseball writers. Over the next week-plus, I’ll be sharing their responses in these electronic pages.

What follows is the product of a lightly edited email correspondence with Craig Calcaterra. Calcaterra, in case you don’t know, made his name by way of his ShysterBall — which blog eventually earned Calcaterra his own damn corner of Hardball Times. Last November, Calcaterra moved over to NBC’s HardballTalk, from which site he quietly manipulates the mind of the common man. (In a good way.)

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Calcaterra: It’s all about the women, really.

Wait, that’s not true.

In all honesty, it began as escapism — I hated what I was doing as a lawyer day-to-day, and baseball was a nice way to think about things other than rich people suing other rich people for a little while. I couldn’t really watch games in the office, and I couldn’t sort baseball cards on my desk, but writing about it (a) scratched the itch and (b) made it look like I was working on real stuff, so no one bugged me about it. I wish for my legal career’s sake I was lying about it, but that’s the truth.

As I really got into it, the motivation to keep doing it became less of a reaction and more of a desire. I realized I was pretty good at it and people liked what I was writing. I got the notion in my head some time in late 2008 that maybe, just maybe, I could get a job doing it, and it was around that time — just before I moved the blog over to The Hardball Times, actually — that I began a conscious effort to make baseball writing a career.

Cistulli: I’m curious: did you know that you weren’t going to like your job? And/or: when did you start to realize you weren’t going to like it?

This is just as much a life skills question as a literary one. I mean, you’re clearly smart. My guess is that you had a good idea of what lawyering entailed before you got yourself involved. If Craig Calcaterra can’t anticipate his own unhappiness, what hope is there for me?

Calcaterra: I didn’t always hate being a lawyer and certainly didn’t expect to hate it when I started down that road. I actually enjoyed it for quite a long time and, since I’ve been away from it, I’m remembering aspects of it more fondly than I thought I would. It was only when my day to day tasks shifted from primarily writing briefs and doing actual trial and appellate work to more client management and supervising of other attorneys that I began to sour on it all. Obviously that stuff is important and it’s what you have to do if you want to be a successful partner in a law firm, but it just wasn’t enjoyable for me and, frankly, I wasn’t as good at it as I was the pure legal stuff.

At the same time, my personal life changed a lot. My wife and I had two kids in the space of nineteen months and, not surprisingly, my desire to stay late at the office — which is another thing you have to do if you want to be a successful partner at a law firm — declined precipitously. Maybe that’s just a fancy way of saying “it’s not you; it’s me,” but the fact is that the private practice of law and I went through a long process of estrangement. If it hadn’t been baseball writing saving the day it would have been teaching or a job with the ACLU or something else. My last year before jumping to NBC was spent at the Ohio Attorney General’s Office. Released from the billable hour and the need to manage insane clients, I actually started to warm back up to the law again during that time. If this baseball writing thing doesn’t work out to me, I could actually see myself returning to the law, albeit only in the public sphere.

Cistulli: Before you entered law school, was there ever a hint that you’d become Craig Calcaterra, Official Baseballing Journalist? A writer of any sort?

Calcaterra: When I was a teenager, I had it in my head that I would be a sportswriter. I’m not exactly sure why, but I read a lot of good sportswriting and I thought it would be really cool to do it myself. I even reached out to a couple of sportswriters in my hometown to talk about what I’d have to do in order to become one and wrote a guest baseball predictions article for the 1988 season for the Parkersburg, WV Sentinel (and they weren’t half bad predictions, if memory serves). My family took a trip to New York City when I was 15, and I actually had them take my picture standing in front of the Columbia School of Journalism (and no, you can’t see it because in it I’m wearing the most unfortunate pair of Jams ever created). I’m not sure exactly when that all changed or why, but journalism was certainly off my radar as a career choice by the time I started college. By then it was a contest between law school and grad school, and the former won because (a) my LSAT scores were higher than my GRE scores, and (b) I wanted to make a great deal of money.

Later career regrets aside, that probably ended up being the best decision I could ever make. If I had gone to journalism school I would have been taught what all J-school students are taught for four years: “Be balanced! No one cares what you think!” Instead I went to law school where I learned how to analyze a fact pattern, pick a side, marshal evidence to construct an argument, write clearly and persuasively, and to anticipate and adapt to criticism and attack. Given the kind of baseball writing I do, I couldn’t have drawn up a better curriculum.

Of course it there was a lot of luck that made that actually happen, but now that it has, I’m realizing that writing about baseball day is pretty much exactly what I thought it would be when I was dreaming about it. This was a strange realization for a cynic like me. No experience I’ve ever had before had been as good as the preceding anticipation, but this is. I still get to use all of my analytical and writing skills that I developed in law school, but now I get to use it on fun stuff. And I get to do it in my pajamas. And people send me free books all the time. It’s quite the scene, man.

Above all else, I really, really like writing in and of itself. I’d write about cars or wars or electronics or rare whiskeys if someone would pay me to do it, but baseball happens to be the one thing I know most about, so it makes for a nice little convergence of personal and commercial interests.

Cistulli: You say you like writing a whole bunch, that you’d write about anything. From my experience, however, the writing process itself can be quite tedious. Is this just not the case for you? Or is there a pleasure that writing provides beyond the tedium of composition, revision, etc?

Calcaterra: The writing process can be challenging. I don’t consider myself “a natural” or anything, and even my most seemingly laid-back writing takes a lot of effort. But I’ve never found it tedious. I actually get pleasure from the composition process. The time I spend in my own head space working out the arguments and the language of the piece I’m writing is very rewarding to me on some selfish level. I’m an out of shape schlub, but the closest I’ve heard anyone describe the feeling I get when I’m writing is the feeling non-schlubs get after a strenuous workout: some pain and toil, sure, but followed by a certain euphoria. I guess workouts lead to an endorphin rush. I get the schlubby, in-front-of-the-computer-all-day version of that. Dork-orphins, maybe.