We mean season in the "brief period of time" sense, as opposed to the baseball season. At any rate, Daisuke Matsuzaka will have Tommy John surgery, all but ending his career with the Red Sox (he likely won't return until halfway through next year, the final one of his contract).
Almost immediately, Justin Bopp at Beyond the Box Score opines: "… further confirmation that the Daisuke contract is one of their worst decisions ever."
Now, this is obviously wrong in a number of ways, not least because the Sox in their history have made so many horrible decisions both on and off the field that Matsuzaka isn't even close to the top.
From trading Tris Speaker to letting Ed Barrow leave to become GM of the Yankees to commencing the fire sale to New York shortly thereafter to Tom Yawkey's refusal to integrate the club until he was the last owner standing to the Sparky Lyle trade to forgetting to mail Carlton Fisk a contract to the Jeff Bagwell trade to lowballing Roger Clemens, the Sox pre-Epstein made some horrific personnel moves. And this doesn't count the boneheaded hiring of boneheaded or past-their-prime managers like McCarthy, Higgins, Zimmer, McNamara, (Jimy) Williams and Little, nor does it count the horrific on-field decisions these managers made to cost the Sox playoff appearances, pennants and championships in 1948, 1949, 1978, 1986, 2001 and 2003, among other years I'm surely forgetting.
Finally, Matsuzaka's contract itself is not actually any worse than some of Theo Epstein's stinkers from years past. If he never pitches another season for Boston, the Sox will have paid Matsuzaka $52 million for 10.4 wins, according to Fangraphs. That's exactly $5 million per win, which is right in line with what teams are paying for value these days. According to Fangraphs, the Sox received $44 million in value, again assuming Matsuzaka never throws another pitch for them. Does anyone doubt John Henry's getting at least $8 million in insurance money for Matsuzaka's lost season. Notwithstanding the insurance money, an $8 million gap in value would be less than the Red Sox paid Julio Lugo to play for someone else in 2010, and is exactly what the Sox paid Edgar Renteria to play elsewhere for three seasons (on top of the $2 million gap between his salary and performance for the season he played in Boston.
Comparing Daisuke to Lugo and Renteria isn't doing him any favors, but unlike those two players, he was actually worth his salary in three of his five seasons thus far, at least according to Fangraphs. But Fangraphs looks at peripheral stats and ignores actual runs allowed in determining its WAR totals. Baseball-Reference pegs Matsuzaka a win less, mostly because he allowed a lot of runs with decent peripherals when he pitched in 2010. Either way, Matsuzaka had two seasons where he was unquestionably worth his contract, which is more than can be said for Lugo or Renteria, and one of those seasons was a three-win rookie campaign in a season when the Sox won the division by two games, followed by a postseason in which he won Game 7 of the ALCS and Game 3 of the World Series. Those wins are easily worth far more than the rate calculated by Fangraphs.
So the contract: Not great, but not horrible. Certainly not "one of their worst decisions ever," unless "their" is referring to Theo Epstein and John Henry, in which case still I wouldn't put it anywhere close to the twin shortstop debacles, and Mike Cameron and John Lackey currently have the privilege of being ranked above Matsuzaka's contract, as well. I'd view it more in line with the Hanley Ramirez-Josh Beckett trade: defensible, led to some fantastic results, not sure if it was worth the cost.
Now, Justin is likely making the common mistake of lumping the posting fee in with the contract; the contract itself was more than reasonable for a pitcher of Matsuzaka's caliber and pedigree, while the posting fee was audacious (some would say outrageous). But there are considerations that ameliorate the cost of the posting fee. First, the cost didn't have to come out of the Red Sox' budget, which means Henry could have scrounged behind his couch cushions for Benjamins (not Amelie, we hope) to pay it. So unlike a traditional $103 million contract, the Sox as a ballclub aren't necessarily hamstrung by the expense.
Likewise, we don't know how much return on the investment the Sox were expecting for that initial outlay, nor how much they received. If the Matsuzaka signing paved the way for the Hideki Okajima signing, then the Sox certainly received more benefit than we would initially credit. Likewise, there's some evidence Junichi Tazawa also followed that path because of the Sox' highly publicized success in 2007 with two Japanese pitching stars, and Tazawa still has promise as he recovers from his own Tommy John surgery. Then there's the Japan-Boston connection. Did the Sox receive anything close to $51 million in ad revenue out of having Matsuzaka on their team in those early years of the deal? Probably not, but they certainly received something, and we don't know what it is.
Finally, there is the nearly unquantifiable notion that the Matsuzaka posting fee/signing energized a fanbase reeling from the 2006 debacle. We all remember those days, right? Following Henry's plane from California to Boston, late-night posts on YFSF, SOSH and elsewhere, etc. It was a crazy month, one that undoubtedly led to renewed enthusiasm for the 2007 Sox and the consequent ticket and merchandise sales, though the extent to which these benefited the Sox above what the market would have been is extremely difficult to tease out (especially since merch sales are split among all 30 teams).
I think it's safe to say John Henry did not get his money's worth for everything he spent on Daisuke Matsuzaka; the Red Sox ballclub clearly hasn't received the full value of his contract in on-field performance (though a combination of performance and insurance may actually make it a wash, if not a slight gain). But the Sox received two great seasons, won a World Series with him and opened a door to a nation of baseball fanatics hitherto focused principally on just the Mariners and Yankees.
Would the Sox make the deal again? It's hard to say, which I guess means it's not the unqualified disaster many are likely to describe it as.