I had a lot of fun Tuesday night, serving as a guest lecturer-really, Q&A target-for the Sabermetrics 101 class at Tufts University in Boston. Along with Baseball Information Systems’ Steve Moyer, and at the behest of my friend Dr. Andy Andres, I got to spend a few hours talking about matters serious and otherwise with a group of students who, had this been 20 years earlier, might have been engaging in thrust-and-parry with Gary Huckabay, Clay Davenport, and others on

I absolutely love events like this, where I get to talk about what Prospectus has done and is doing, but also about baseball and performance analysis. One of the things I miss is participating in the BP annual’s book tours that come in the spring, with the chance to have these back-and-forths with people, some who have been reading us for 15 years, others who just saw the crowd and meandered over. There’s always been an element of proselytizing involved in working with BP, and it’s something that I’d come to love over the years. Sitting in that classroom, touching on any number of topics-wishing at times I’d had one of the truly smart guys with me when a statistical query stumped this dumb journalism major-will definitely be one of the highlights of the year. I’d like to thank Andy and his students, as well as Steve and BP’s David Laurila, for a great time.

Being in Boston, however briefly, has me thinking about the hometown nine, which could be in line for an interesting offseason. When I look at the Red Sox, I see the best organization in the game, one that has raised itself to the point where consecutive seasons of not winning a pennant leave the fan base restless. The transition I’ve talked about with the Yankees, where there’s a disconnect between what the reality was for fans in the late 1980s and early 1990s with what came after, seems to be developing in Boston. In six years, this franchise has gone from “please win the World Series before I die” to “how come you haven’t won since 2007?,” and all the irrationality attached to that attitude.

It’s these expectations that make it tempting to pay through the nose to upgrade a part of the team that’s already a considerable strength. The Red Sox, with Josh Beckett, Jon Lester and Clay Buchholz, go into 2010 with arguably the best front end of a rotation in the AL. Nevertheless, there’s a clamor for them to acquire Roy Halladay, a free agent at the end of ’10 who has been made available by the Blue Jays. Halladay would make the Sox better in the short term, but not by nearly as much as you might expect. If you trade Buchholz for him, the upgrade is perhaps 15-20 runs saved over 220 innings, or about two wins. If you can acquire Halladay without trading Buchholz, it’s a bigger upgrade depending on how you project Michael Bowden or Tim Wakefield or perhaps a mid-level free agent to do.

There’s a reason for making this kind of upgrade. The Sox are in the range where marginal wins have the most value, moving a team that much close to a postseason berth. The competitive environment of the AL East, with strong Yankees and Rays teams, requires higher standards than does the rest of baseball. Certainly Halladay would make a postseason rotation even more formidable, and if the postseason schedule is compressed in 2010, having an additional starter who can carry a significant load will be even more valuable.

On the other hand… you’re trading for one season of play. That’s 34 starts, 220 innings, plus whatever may happen in October. You may even have to agree to a risky long-term extension to complete the deal, as Halladay has a no-trade clause, and like any player in this situation, he would certainly welcome the chance to secure his future without taking the risk that he’ll get injured in the upcoming season. There won’t be any discount; Halladay has the leverage and can comfortably compare himself to CC Sabathia and Johan Santana, each making more than $20 million per season. So to acquire Halladay now is to take the worst of both worlds: paying in talent and having to commit to a market contract for his future, all at a gain of one season’s upgrade.

This is also the Jays’ problem. Just as the Twins were forced to take less for Santana than it was assumed they would, the Jays may be stuck choosing between an unimpressive package of prospects for Halladay and allowing him to leave at the end of 2010 for two compensatory draft picks. Neither the Red Sox nor the Yankees were willing to trade their best prospects two winters ago, nor would Santana agree to a deal that didn’t include a contract extension, leaving the Mets to swoop in with a package that now reads like a bad joke. The Jays’ challenge is to not make that same mistake, and given the parameters-you’re effectively trying to make the best trade for three parties, not just two-it may be impossible.

Red Sox fans may want Halladay, but the team has little reason to pay through the nose, twice, to get him. There’s certainly a price where it makes sense for them to make a trade, but if they have to deal Buchholz, if they have to deal Casey Kelly, and if they have to commit to 2011-2016 at a staggering rate, then they are probably better off having “just” a very good rotation, focusing on improving the back end of it and the bullpen, and adding parts to what may be the most flexible mix of position players in the game. The Red Sox are not about going all-in for one season at a cost of many others; they’re about winning 95 games every year. If they can trade for Roy Halladay within that framework, fine, but whether they do so or not doesn’t change the caliber of this franchise.

Hallday wasn’t the big story while I was in town. No, there were two others, the first of which involved Dustin Pedroia‘s willingness, even eagerness, to play shortstop. Pedroia was a shortstop in college and for a chunk of his time as a prospect, moving to second as he approached the majors. He’s a good second baseman, not a great one, and just based on his skill set I suspect he would be a slightly below-average shortstop, costing maybe five to 10 runs a season with his glove. The main problem I see is that his size would seem to limit his lateral range and his throwing arm, making him comparable to David Eckstein at the position. A shortstop who fields like late-20s Eckstein and hits like peak Pedroia is a very good player, so that’s actually a reason to move him.

The issue is that it’s making a move for the sake of making one. The Sox don’t have a strong internal option forcing Pedroia off of second base so much as they see a free-agent pool longer on second basemen than shortstops. So rather than sign a sure-to-decline Marco Scutaro or Miguel Tejada, they see picking up Orlando Hudson or Felipe Lopez, both a bit younger, as the stronger play. I see the rationale, but rather than move a key long-term element of the team from his best position, I’d rather see them roll the dice on moving someone like Hudson to short. The equation is much the same, and the level of investment in the move is significantly less. If it fails, you haven’t messed on up a core contributor, just cost yourself some runs and money and forced yet another midseason trade for a stopgap. Heck, the Sox could even run Jose Iglesias out there by August, eating the 550 OPS in exchange for the +20 defense.

Think about 1997, when the Red Sox moved their fantastic incumbent shortstop to second base, over his strenuous objections, to make room for Nomar Garciaparra. John Valentin was moved because there was a better player on hand, and the move was designed to maximize the talent on the field. Moving Pedroia, while similar on the surface, is a move of convenience based on the fleeting makeup of one year’s available talent. Moving Pedroia for that reason is a mistake, and while it could work out, the risk involved is significant and not worth it for the difference between signing Hudson and signing Tejada. The Sox can find a better plan.

The other story of note was John Henry proposing changes to how MLB redistributes money. Shockingly, his plan would have the greatest effect on the Yankees, as it focuses on high payrolls rather than high revenues. It was self-interest disguised as economics, and should be condemned as such. Henry correctly questions the efficacy of wealth transfers approaching a billion dollars to a number of teams that do not appear to be using that money to change their competitiveness. His solutions, however, are unoriginal-yet another call for guaranteeing a portion of revenues to the players in exchange for payroll constraints-and, as all owner plans have always done, fails to address the central problem.

Henry is a smart man, a successful man, a man who has made his wealth based on knowledge of finance and economics and the use of hard data. So why won’t a man like that acknowledge what outsiders such as Keith Woolner and Derek Zumsteg have known for years: that the problem MLB faces isn’t an issue of payroll or revenues, but the differences in potential revenue that have developed across markets in the past 30 years? A man with the background of John Henry has to understand that central point, and yet he presents a plan that would do absolutely nothing to address it.

Smart, serious people have presented well-crafted solutions that directly address this problem. The first owner to take up one of these solutions, to back a plan that has nothing to do with limiting labor costs or hindering the competitiveness of a rival or dipping into the public till is the owner I will take seriously on this topic. The problem of differing incentives across markets is the one that drives everything else, that makes it profitable and even sensible for the Royals and Pirates and Marlins to be run in the soul-crushing way they’ve been run for more than a decade. MLB has never once attempted to address this, and the plans they’ve enacted have made the problem worse. Until fixing the marginal-revenue problem becomes the game’s top priority-and it is very reparable-no equity among markets is possible.

I want to know why one of the smartest, most accomplished, most economically-literate men in baseball won’t embrace a real solution.