ESPN's Buster Olney tweeted on Monday that, according to a source, the Boston Red Sox were "aggressive in the pursuit of Ryan Dempster." This simultaneously made sense and was a bit strange. Dempster is going to be relatively cheap at the July 31 deadline, compared to the likes of Matt Garza, Cole Hamels, and Zack Greinke, but he's also talented and durable enough that the price isn't going to actually be cheap.
This is why it was suggested on Monday, in the hypothetical Armchair GM series, that Dempster is worth asking about, but, in reality, might not be better than what's already in town (i.e., the starting pitcher edition of Franklin Morales, and a seemingly-resurgent Aaron Cook), with the added negative of costing Boston prospects -- and to a team whose front office knows a thing or two about what the Red Sox keep in the cupboard. Dempster is leading the NL in ERA at present, but it's not as if Boston is helpless with their own latest additions: Cook's 3.34 ERA in his nearly 30 innings and five starts isn't entirely real, but it's also real enough to be of value to Boston, and Morales has been outright dominant at times as a starter, thanks to finally harnessing the command of his stuff that always lacked in Colorado.
The language in a note from Alex Speier yesterday makes more sense, with the Red Sox "not actively pursuing" Dempster, a phrase that makes it sound like they're doing their due diligence, and checking in on the price on a potential major piece of the trade deadline picture. Dempster is reportedly willing to pitch for any contender, and he's a straight-up rental without any post-2012 strings attached, thanks to the new collective bargaining agreement's rules on pick compensation, so it's in the Red Sox' interest to at least check to see what the price is looking like.
He's not a great fit, though, since the Cubs want to pay his remaining salary in order to increase the quality of prospects coming back. There's no need for them to force a deal with Dempster, either, as it's likely someone will pay up by the time July 31 rolls around, and if not, his 2012 performance has been such that, were the Cubs to extend the $12.5 million qualifying offer to him -- the new CBA's replacement for the Elias Rankings in pick compensation -- they would more than likely find someone to bite on Dempster, getting draft picks in exchange for losing the righty.
Thanks to the second wild card, there are more clubs in potential playoff contention than there aren't at this stage, and the Cubs, unlike many with potential assets to move, are one of the few who are clearly out of things. That means everyone else will be calling them, rather than the other way around, and it's likely Dempster won't have to wait until the off-season to find a new home because of it.
Were Dempster still able to bring in compensatory picks to his new club, or were he under contract or with an option for 2013, this would all be a different story, in terms of Red Sox interest. But Boston is more likely to give up prospects for something with a tangible, 2013 nature to them, rather than on a rental at a time when their rotation is as right as it's been all year, and the Cubs just have no reason to shop him at the kind of price that would make sense for the Red Sox.