Dec 14, 2009, 06:05AM

Defying the Recession: From Lawyer to Fulltime Baseball Blogger

Craig Calcaterra says goodbye to his Midwest legal practice and now puts bread on the table for his family by blogging about baseball.

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The following is the fourth in a series of conversations with Craig Calcaterra, the increasingly well-known baseball blogger who first appeared on the Web with Shysterball. Calcaterra is passionate and opinionated about the sport, yet is also perhaps the most entertaining (and unorthodox) professional writing about baseball today. He recently put away his lawyer’s sheepskin and posts almost around the clock for Circling the Bases, an offshoot of NBC Sports. We conducted the following interview this past weekend.

Splice Today: You've made a career move that in perilous economic times has to qualify you as one of the few winners. In the past, on Shysterball, you've made some jokes about being a lawyer by day, and rambunctious baseball blogger by night (and whenever you could sneak in some posts), but certainly you'll miss some aspects of the legal profession. Right?

Craig Calcaterra: I can only think of two. First, I had the pleasure of working with some really smart and really nice people over the years. Now I work with my cat. The cat's nice, but you can't talk about books and politics with him. Second, I did get a rush doing oral arguments at the court of appeals and stuff like that, and I can't really see a way to replicate that doing what I'm doing now. I may discover a couple other things as time goes on—it's only been two weeks since I gave up the legal business—but as I sit here today, I won't miss a single bit of the day-to-day business of being a lawyer. It took me over a decade to figure it out, but I'm really not wired for that line of work.

ST: Aside from the hustle-bustle of agents and general managers at MLB's winter meetings last week in Indianapolis, and schmoozing with other writers, what surprised you most about the experience, and how did it compare to past conventions you've attended?

CC: This is going to sound really shallow, but I was surprised at what managers look like out of uniform. The players just look like athletes in street clothes, which isn't all that surprising. The managers are all over the map. Tony La Russa, Bobby Cox and my father are all roughly the same age. My father looks his age. Cox seems like he's much older. La Russa dresses and carries himself like he's in his 30s. Manny Acta looks like he's ready to jump into a number from West Side Story. As for the conventions: The trade show where they peddle bats and stadium seats and AstroTurf and caps and everything was like any other trade show. The rest of it—like, the actual meetings—are a pretty subdued affair. Most conventions I've been to get rowdy at about seven p.m. The Winter Meetings quiet down around then as all the print journalists start typing everything they learned all day in order to make deadline.

ST: Which of the three (as yet) unsigned free agents—John Lackey, Matt Holliday and Jason Bay—do you think will be most disappointed by the contract he eventually gets? And if you were a GM which of those players would be at the top of your list?

CC: I think Jason Bay. He's got offers from the Red Sox and Mets right now in the four-year $60 million range and I can't see him getting a ton more than that. That's nothing to sneeze at, but he probably expected better. If I was a GM I'd be most interested in Holliday because he's got a better all-around game than Bay and is younger, while I think Lackey only looks like a stud this winter because there aren't any other really good free agent pitchers out there. To be honest, though, I think just about any team could live without these guys next season, at least at the prices they'll ultimately command. It's a weak crop.

ST: Now that the dust has settled on the Yanks/Diamondbacks/Tigers deal, who came out on top? I can't stand the Yanks, so I was especially disappointed that Curtis Granderson, who by all accounts is one of the great guys in the game (with a terrific future in television broadcasting), but it also surprised me that Brian Cashman coughed up Austin Jackson so easily. I thought he was an "untouchable."

CC: I think the Tigers did. They'll probably be a bit disappointed by Austin Jackson—I don't think he's ready to slip into a full-time gig in center field just yet—but in the long term they'll be really happy with Max Scherzer. I think that he, and not Granderson, is the most valuable player in the deal, and when you leave a deal with the best player in it, you've usually won. He struck out 174 in 170 1/3 innings in his first full-time action. He has a mid-90s fastball and a great slider. I like Granderson too, and I think he'll do well with that short right field porch in Yankee Stadium, but I think he'll be on the downside of his career just as Scherzer is putting himself in the Cy Young conversation every year. As for Arizona. man, I have no idea what they were thinking. The deal makes no sense for them. At least none that I can see.

ST: Perhaps it's my imagination, but this MLB post-season/hot stove seems like the strangest in years. Teams are pleading poverty (some true, some probably not; the Twins have always been stingy), the Texas Rangers' ownership is in flux, the Dodgers' ownership is in soap-opera land, the free agent pickings are very thin, and the economy has owners, GM's and agents in grumpy moods. Do you agree?

CC: It is strange and that several teams have non-baseball things driving the decision-making, most notably the Rangers and Dodgers. I think, though, that there's a big political thing happening too. Last year everyone predicted doom and gloom on the revenue side, and they were probably right to predict it. Except things ended up not nearly as gloomy as expected. Revenue went down, but not by nearly as much as feared. Now teams have a bit more money than they thought they would, but they don't have anything good to spend it on. So they do things like pay Brandon Lyon $15 million over three years and give Pudge Rodriguez and Jason Kendall two-year contracts. I think once the spring comes, we'll look back and see that a lot of dumb contracts were given out.

ST: My 15-year-old son, a Red Sox fan like his dad, is driving me nuts. He ruled his fantasy league last season, knows every prospect in the Sox organization, and backs up our discussions about this or that team's needs with so many statistics that I can't get a word in edgewise. The other night, he was actually annoyed with me for suggesting that Theo Epstein sign Adrian Beltre to play 3B for the Sox, citing Beltre's decreased offensive production in 10 different ways. Is it your sense that serious baseball fans—the same kind that a generation or two ago would pore over the agate type in daily newspapers—are a lot more knowledgeable today, or am I just a crusty old codger?

CC: Are those things mutually exclusive, Russ? Seriously, though, I do think that being a serious fan means something very, very different today than it did 20 years ago. Heck, even 10 years ago. When I was your son's age I got The Encyclopedia of Baseball from the library. Even though it didn't have any stats that were less than three years old in it, it qualified me as the hardest of the hard core. Today the information at one's disposal is simply incredible. Sure, it's possible to still be a casual fan who simply watches and enjoys games and maybe reads a notes column once or twice a week, but, if you're so inclined, there is virtually no limit to the amount of information, statistical or otherwise, that one can consume.

ST: About the Red Sox: Much has been made about Epstein's implication that 2010 will be a "bridge" to the future (he obviously couldn't say "rebuilding year"), but I'm betting that if the Sox don't field a team on Opening Day that has the usual look of a contender, that record string of sellouts at Fenway Park will end sometime around Memorial Day. What's your take on that, and the A.L. East in general for next year?

CC: I agree, the sellouts will end if the team isn't challenging for the division lead all year. Going to Red Sox games has become a very fashionable thing to do, but on the whole, Boston fans are sharp, and they won't stay enthused if the team isn't both winning and interesting to watch. Right now I think it's too early in the offseason to know for sure—Theo could pull off a trade for Adrian Gonzalez and change the balance of power—but if the season started tomorrow, I think New York would win the division easily and Boston would spend most of the year fighting off the Rays, Angels, Mariners and Rangers for the Wild Card.

ST: Why haven't the Braves bought or traded for a bat to go with their pitching?

CC: They have it in their mind that calling up Jason Heyward sometime in May or June will be the equivalent of adding a big bat. Of course they're delusional if they think that they won't be too far down in a hole by then if they don't have viable bats at first base and right field before then, which could easily happen. Ultimately, though, they have a pretty hard budget imposed upon them by their corporate masters at Liberty Media, so adding a Bay or a Holliday really isn't possible. If they trade Derek Lowe they might have some wiggle room, but they'll probably just use that money to pay Adam LaRoche or someone like him.

ST: Do you share the opinion that Billy Beane doesn't look so smart anymore? And now that the movie based on Moneyball is back on, how in the world will the director make a two-hour picture about on base percentage/no giving away outs via sacrifice bunts the least bit compelling?

CC: I think the key thing to take away from Moneyball was not on base percentage or the eschewing of small ball in and of themselves, it was doing something—whatever it was—that the other teams weren't doing, thereby neutralizing the other teams' financial advantage. Not long after Moneyball came out, however, just about every team started focusing on OBP and all of that too, only they had more money than Beane, so his advantage was gone. Ultimately Beane isn't any less smart than he was. It's just that everyone else got smart too and he's still broke.

I think Moneyball could be a good movie if it takes a major left turn from the book and just has fun with a story about a rakish underdog beating the big boys in a baseball setting. Go back and read the book and ignore the stats talk. There are a lot of good anecdotes in there.

ST: We've touched on President Obama in the past. Now that he's completed almost a year in office what do you rate as his biggest accomplishment and biggest disappointment?

CC: I think his biggest accomplishment has been in changing the tone as opposed to any specific piece of legislation or policy initiative. We now have a president who approaches issues with pragmatism and realism rather than from a pure ideological perspective. We now have a president who appears to grasp the enormity and seriousness of his job as opposed to one who views winning petty political victories as his most important mission. Obama hasn't done everything right. And some of the big things he's trying to do now may backfire. He's human. But I sleep pretty well at night knowing that the man takes his job seriously and puts thought into what he does.

Biggest disappointment: I think he has jerked the gay community around an awful lot. He had tremendous support from and made an awful lot of promises to that community during his campaign, many of which he could have fulfilled by the stroke of a pen (repealing “Don't Ask Don't Tell”; changing Department of Justice litigation strategies) and didn't for fear he'd take political heat, I presume. The one thing he might point to as an accomplishment in this arena—the passage of a hate crimes bill—is an utterly empty accomplishment given that hate crime laws are shallow, ineffective and, in my opinion, Constitutionally-questionable gestures to begin with.

I truly believe that we are going to look back 20 years from now and be outraged that there was a bona fide "debate" about whether people should be allowed to get married, hold certain jobs and provide for their families and economic futures in the way they see fit simply because of who they are and who they love. There are people who are far more wrong on these issues than Obama, but he's ultimately the boss, and his failure of leadership on this is pretty depressing.

ST: It's the holiday season: if you had to name one indispensable baseball book to give to a teenager (or precocious pre-teen) what would it be?

CC: It's getting a little long in the tooth and is due for an update, but I'd still say The Bill James Historical Abstract. There's just so much history and flavor in that book that I couldn't imagine being a baseball fan without it. You can ignore the stats sections entirely and just read the decade-by-decade recaps and top-100 player profiles and come away from that book as the most knowledgeable baseball fan on your block.

ST: Which team will draw the fewest fans in 2010?

CC: The Athletics. They're already at the bottom of the barrel in recent years, and the big push to move them out of Oakland—joined by team ownership, city officials and soon all of Major League Baseball—will cause what's left of that fan base to remember that there are many better things to do in the Bay Area during the summer than to sit in a neglected ballpark watching a team that is virtually on the I-880 on ramp to San Jose already.

ST: You've said in the past that you're indifferent about the Orioles because they're, well, boring. Recently, you had a more optimistic post on the team's future. Care to expand? As someone who lives in Baltimore and attends about 20 games at Camden Yards, I'm not sure Kevin Millwood does much of anything, although I suppose he'll eat up some innings. And although I'll be bombarded with nasty comments from local O's fans, I'm not sold on Adam Jones as a superstar: my wager is he goes the Alex Rios/Vernon Wells route, as opposed to Matt Wieters, who's the real deal.

CC: I'm not ready to crown the Orioles—heck, they'll still probably have a losing record next season—but they're moving in the right direction and they're interesting. It's just little stuff now like giving fewer plate appearances to well-traveled veterans guys and more to Wieters and Nolan Reimold. Real excitement will start to build if one or all of the young pitchers—guys like Brian Matusz and Jake Arrieta—show some promise.  Basically, any team that is moving in one direction, whether it’s up or down, with any sort of momentum is interesting. The Orioles are moving up and they are thus no longer a team I consider boring. The new boring team: the Astros. They're gonna get all of my barbs next year.

ST: Finally, now that you've shed the nine-to-five (euphemistically, I understand that lawyers put in incredible hours) straitjacket, do you plan to take Carleen and the kids on an extended trip around the country next summer and visit a lot of ballparks?

CC: Not if I want to stay married. Carleen is a wonderful wife and mother, but she is not a baseball fan. The best I'll do with her is to catch a Columbus Clippers game or two. I may be able to get my kids out on the ballpark trail eventually, but as they're just four and six, that's a few years down the road.

  • This was a fun interview with a guy who knows baseball but apparently doesn't take himself too seriously, like a lot of the bloggers at ESPN. One quibble: I liked "Moneyball" but I can't for the life of me see how it becomes a decent movie, unless there's unusual poetic license allowed.

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  • Whew, it looked awfully long, but it was interesting. Good questions, good answers. Thank you. Maybe it's time I read the Historical Abstract. I understand that the 15-year-old thinks the White Sox will be good. Let it be so.

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  • That 15-year old is right, the white sox will be good, not 100 wins good, but good nonetheless. As of now, they are easily the favorite to win the division, with the addition of Peavy and Rios, that is if they can bounce back. Kenny also has to sign a DH and RF, but that won't really be hard. Vladimir Guerrero will go for a 1year/5.5MM deal. Options for right are Johnny Demon, Mike Cameron, and Coco Crisp. If Kenny can do this, the playoffs are all but guaranteed. The pitching staff is good as it is, and may be own of the best in the AL. Buerhle-Peavy-Danks-Floyd is a great rotation. The Teahen signing was almost genius, not only is he a good fielder but all the line drives he hit Kaufman will turn into home runs at Cellular. Carlos Quentin rebounding is essential, too, because for once, the Chi-Sox aren't loaded with power. I can't see anyone else in the AL central that would be a serious contender, outside maybe the Twins, only because they always seem to compete.

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  • I agree that Bay will be very disappointed with his contract. With Lackey getting the money he wanted and the Sox signing Cameron, I just don't see Bay getting anything above 4/65. But hey, there's always the Mets. You can never predict what Omar will do.

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  • russ...you set up a debate and i'll happily go toe to toe with this character. we can video tape it for the world to see.

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  • my first comment is in response to his comment: Second, I did get a rush doing oral arguments at the court of appeals and stuff like that, and I can't really see a way to replicate that doing what I'm doing now.

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