Originally written on WHYGAVS?  |  Last updated 11/16/14
I have a little mental tic where every time any big trade goes down involving any baseball team, I ask myself what it would take for the Pirates to complete the trade themselves. This was born, I think, during the Dave Littlefield era when the Pirates would only rarely target players I thought they should be interested in. I'd see players that I wanted the Pirates to acquire headed to other homes and I'd ask myself if the Pirates were even capable of completing the trades that I wanted to see them make. Under Neal Huntington, the Pirates have been much better about acquiring players that I'm happy to see them acquire, but I still evaluate a big chunk of baseball's biggest deals in my head this way.  When the Marlins traded a huge chunk of their roster to Toronto last night, my first thought was this: "The Pirates would be win the NL Central next year with Mark Buehrle, Josh Johnson, and Jose Reyes." My second thought was this: "That is true, but crazy." My third thought was, "Seriously, they could never afford that trio and they'd have to gut the farm system for a crazy one-year run that would probably end horribly anyway." In my head, though, I kept constructing a trade because these are the things that I do in my head. After I put together a prospect package, I imagined a panicked Neal Huntington trying to make the case for this deal to Frank Coonelly and Bob Nutting and getting laughed out of the room.  The Pirates getting in on the Marlins Fire Sale is a ridiculous concept, of course, for the ideas laid out above, but one part of that idea stuck with me. If we accept that the Pirates are at a better point today than they have been on past November 14ths, but that they're still a massively flawed baseball team (they are) and we assume that Neal Huntgton has to get the Pirates at least above .500 and probably into the playoffs in 2013 to keep his job (I'd say that he probably does), then I think that a huge question worth asking is how Huntington is planning on approaching this off-season.  After five off-seasons at the helm, it's not hard to discern Neal Huntington's off-season strategy: look for bargains everywhere. Look for them on the trade market, look for them in free agency, look for them on the scrap heap. In general, this has not yielded a ton of huge returns for the Pirates. Really, you can argue that outside of the bullpen, the only two off-season acquisitions during the entire Huntington era that have helped the Pirates at all have been Garrett Jones (who was a needle-in-a-haystack miracle) and AJ Burnett (who fell into the Pirates' lap). That'd be fine given the market realities of being the Pittsburgh Pirates in 2008-2012, except that the Pirates have tried and failed to fill legitimate holes with free agents (Bedard, Barajas, Barmes, Church, Crosby, etc. etc. etc.) and trades (Iwamura!) over the winter.  It's tricky to try and gauge what that means for this winter: on one hand, Huntington might feel the urge to do something drastic to save his job, but on the other hand if he does do something with long-term ramifications (say, signing Edwin Jackson to a four-year/$60 million contract), he'll be the person that has to deal with it if it works out. He's also the person that presumably has the most faith in the methodology of this front office, because it's his front office.  And yet, it's clear that the way that Huntington has approached the off-season in the past hasn't yielded good results and whether or not Huntington thinks his job is on the line, changing the team's off-season approach can't hurt. I'm guessing that if it's going to be different this winter, it's going to be centered on how the Pirates handle arbitration-eligible players. Joel Hanrahan is due to make about $7 million in arbitration, which is a huge chunk of the Pirates' payroll. Jeff Karstens is due about $5 million, which is a lot of money to pay a starter who's unlikely to throw more than 120 innings. Dejan Kovacevic, in particular, has been saying all fall that Karstens probably won't return. Whether the Pirates should keep Karstens or not is certainly its own discussion, but these are the two guys to keep an eye on when figuring out if the Pirates are going to take a different path this winter.  Either way, this is less of a prediction and more of something to keep in mind as the hot stove heats up. The Pirates have been pretty quiet so far this winter, but I'd be surprised if that lasts much longer. 

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