Media eInterviews: Craig Calcaterra

Hardball Talk’s Craig Calcaterra is well-known for his Shysterball blog of yore, but perhaps he hasn’t been prodded about his old profession enough. He was gracious enough to answer my pestering emails in between wondering about Bartolo Colon’s gut and Andy Pettitte’s will to go on.

Eno Sarris: Set the scene, tell us a little about your youth. Where did you live growing up, where did you go to college, what did you study, and where did you go to school after that?

Craig Calcaterra
: I was born in Flint, Michigan and lived there until I was 11, when I moved to Parkersburg, West Virginia. We lived there three years, and then we moved 120 miles south to Beckley, West Virginia where I went to high school and eventually graduated. For reasons I’ve explained elsewhere, I consider Beckley my hometown. I went to Ohio State University — far enough away to where I felt like I was going away to college but close enough to home to not feel like I was going too far — where I majored in political science and minored in English and anthropology. That kind of transcript is pretty much tailor made for either unemployment or law school, so I chose law school. After three years at George Washington in DC, my wife and I moved back to Columbus, Ohio were I jumped into the working world.

Childhood was pretty normal. My dad was a meteorologist with the National Weather Service. My mom was a secretary and sometimes waitress. The moves were for when the old man transferred. I have an older brother. We were baseball card fanatics from 1978 until he joined the Navy in 1989. I still have about 100,000 baseball cards in my basement much to my wife’s chagrin. I played baseball and football as a kid, but by the time the tenth grade rolled around my desire to play finally sunk to the same level as my ability so I called it a career. Mostly I was a normal kid just trying to balance his geek-like tendencies against the need to attract females. It mostly worked out.

Eno Sarris: Shysterball readers would remember that you were a lawyer first, but you wrote mainly about baseball on the blog. What was your ‘day’ job like? What did you like and dislike about being a lawyer? Would you ever think about going back?

Craig Calcaterra: I was a litigator. Mostly defending lawsuits for big corporations, but a little white collar criminal defense too.

I talk a lot on the blog about not liking the law, but I’m probably not as even-handed about that as I should be. There were things I liked about it and occasionally even miss. I liked getting a new case, interviewing the client and witnesses and trying to ascertain all of the facts. I liked the detective work involved. I liked taking the first cut at constructing the legal theories. And of course depositions and trials were fun because I really enjoyed the actual stand-up legal work, cross examining witnesses and that sort of thing.

But given the way the legal system works these days, the vast majority of your cases never go to trial, so day-by-day I was in my office, reviewing documents and writing legal briefs. And as I grew more experienced more and more time was spent delegating those tasks in favor of managing cases. Which is kind of a drag, frankly. Reviewing monthly bills. Dealing with a lot of silly political garbage between the clients and the firm (and among lawyers in the firm). If you want to advance in a law firm you need to excel at those things and, of course, at the networking and schmoozing that leads to snagging more clients for the firm. I’m just really not set up for that.

My aversion to the administrative tasks sent me down some weird roads. Towards the end I had stumbled into this odd niche at my firm in which I was not unlike the George Clooney character in “Michael Clayton,” working as a fixer for clients. Getting the CEO’s kid out of a jam. Getting called in to clients’ offices to be the heavy in internal theft investigations. Handling the odd offshoots of the big important cases that the majority of my colleagues were working on and which I didn’t want any part of. It was fun for a while, but I eventually burnt out on it because there was a lot of dark stuff in that little cul de sac and it was getting harder to face it every day.

That’s when I started Shysterball. It was an escape, and I’ll be damned if it didn’t help me literally escape. Would I go back? Maybe, but not to a private law firm. My last year before I went to NBC full time was in government. I was actually starting to like the law a little more by the time I left that gig, and if I had to, I’d consider going back into public service. But only if I had to.

Eno Sarris: Does any of that life color your current life? Are there any litigious leftovers that work their way into your writing (or thinking) now?

Craig Calcaterra: Actually, the legal training and experience has been critical to the type of blogging I do. Most of what I do is opinion writing. Stuff that demands that I quickly consume and process information, pick a side, make an argument, express it clearly, defend it against counterarguments, play devil’s advocate if I have to and all of that. That’s exactly what I did as a litigator. Just on stuff that was way more boring than baseball.

My particular experiences in the law have been pretty useful too. It’s a lot easier for a lawyer to tell when the official statements from the league or teams or the union or networks or whoever are baloney, because I used to help write that kind of stuff for clients and can smell it a mile away. I tend to think that those weird fixer cases, internal investigations and the criminal stuff I worked on helped me understand people and their motivations a little bit better than I used to, so in some instances I’m less credulous than the next blogger might be. In other (rarer) cases a bit more empathetic. This has come in particularly handy when it comes to the politics of steroids, legal issues, labor issues or when the business of baseball comes into play.

I have a lot of mixed feelings about my legal training and career — I don’t recommend that anyone go $120,000 into law school debt in order to prepare oneself for a blogging career — but I certainly don’t regret it because there is no way I could do what I do the way I do it without that training.

Eno Sarris: Could you run me through one particular moment that reminded you of your lawyer days, or in which your skills as a lawyer helped your analysis?

Craig Calcaterra: I used my legal skills most directly for baseball blogging purposes on my old Shysterball blog when the really big steroids stories were hitting in 2007 and 2008. First when the Mitchell Report came out and I close-read the whole thing in the days after it came out and realized how flawed and superficial George Mitchell’s investigation was, then when Barry Bonds was indicted and I went through the grand jury testimony and realized just how weak the government’s case was. It’s amazing to me how credulous the baseball media was of both the Report and the Indictment were. But really, we see this all the time when the government or when quasi-governmental bodies do this kind of stuff. Lawyers tend to question these kinds of things and we’re always better off when authority is questioned.

Less directly, I find myself using my cross-examination skills almost daily. Less to badger people — because, really, that’s no fun — than to discover flaws and inconsistencies in one’s arguments. I try to internalize the cross-examination rather than spell it out in a post because that’s just annoying, but when I write something about why I disagree with Jon Heyman’s Hall of Fame ballot or try to understand why some people won’t vote for Jeff Bagwell for the Hall of Fame, I am conducting a mini-cross-examination in my mind first. “Mr. Heyman, you state that Jack Morris deserves election based on his performance in blow-out games. But you would agree with me,would you not, that Bert Blyleven’s performance in blow-outs was superior?” Or “Mr. Jacobs, you state that your suspicion of Jeff Bagwell’s steroid use causes you to postpone voting for him for the Hall of Fame. But you don’t know if others you support such as Roberto Alomar or Jack Morris ever took PEDs, do you?”

I’m not suggesting that this is some super power. It’s really just the application of logic, critical thinking and a little bit of Socratic method. Some people are great at that naturally. There was never a better b.s. detector than Bill James, and he didn’t go to law school. In my case, however, I was conditioned to think like that through my legal training.

Eno Sarris: Do you have any advice for your bloggers trying to make it in a cruel, cruel world?

Craig Calcaterra: I’m often asked by beginning bloggers how I managed to get myself in a position to make a living by blogging about baseball. In all honesty, however, I was really lucky to get my job and it never would have happened if it hadn’t been for a lot of random happenstance and the extraordinary support of some well-placed people. If I could tell people how to make that happen I’d be able to make a hell of a lot more money as a blog consultant than I do as a blogger. That said, I do have some thoughts on how to write a great blog which, sadly, is often a totally different thing than writing a popular one:

1. Write on a regular schedule. You don’t have to update 6-10 times a day, but do make sure that you post consistently, be it daily, or twice a day or whatever so that readers know what to expect and know when to come back. If you have irregular gaps between posts or go dark for a week or two at a time, you won’t get habitual readers.

2. Write about what interests you. There is nothing worse than reading a blog post that begins “Well, I suppose I should weigh in on x, y, z …” If it’s a chore to you, it will be worse for your readers. If you’re writing about what interests you rather than what you think people want to or need to read, you will keep going even in the face of indifference. Which is critical, because I’d guess that 90% of blogs just up and die at some point because the writer loses interest. The ones that last are the ones written by true zealots who would be spouting that which they write even if no one was paying attention. And the ones that last are the ones most likely to eventually get noticed and maybe — just maybe — blow up into something bigger than just you and your co-workers reading it each day.

3. Find a niche and know your limitations. This goes hand-in-hand with writing about what interests you. There aren’t many people who can cover the game comprehensively in an interesting fashion. It’s a hot mess when I try to do my own statistical analysis, so I don’t do it. Some bloggers are adept at talking about baseball history, others not so much. Some people are better persuasive writers and others are better at more research/analytical pieces. Not everyone is funny. It’s way better to do one or two things really well than to try to be all things to all people.

With a phone full of pictures of pitchers' fingers, strange beers, and his two toddler sons, Eno Sarris can be found at the ballpark or a brewery most days. Read him here, writing about the A's or Giants at The Athletic, or about beer at October. Follow him on Twitter @enosarris if you can handle the sandwiches and inanity.

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Craig was incredibly gracious in taking his time to check out my blog and provide me with some great advice. I am forever indebted. Thanks Craig!