I have to imagine that this is about the toughest spot a general manager can find himself in. With nine days left until the non-waiver trade deadline passes, his team is kind of a mess. Four of the starting pitchers he opened the season with are on the disabled list, two are already confirmed to be out for the season, and there's still a pretty good chance Masahiro Tanaka is going to need Tommy John surgery. His offense is 12th in the American League (and last in the A.L. East) in wRC+, and the big free agents he brought in to turn things around after Plan 189 crashed and burned have been disappointments to this point.
And yet, they're just four games out of first place.
The end result is a murky situation that makes the decision of whether to add pieces for the playoff run or concede that the roster may not be good enough to get that far anyway a very difficult one to make with any certainty, especially given a trade market that doesn't have many potential impact upgrades available. So what's a GM who has to make some choice in just over a week to do? Let's consider the case for each option in turn.
The case for buying
The playoffs are in reach, and these are the Yankees. Yes, this roster has some pretty big flaws. No, they don't look like a playoff team on paper. And no, they haven't played as well as their 50-48 record. But those wins are in the books, and the fact remains that with just four games between them and the Orioles and 38 games against the A.L. East (including 20 against Baltimore and Toronto), the Bombers are still very much in the thick of the pennant race, and should have the financial capabilities to swing a major addition from a team looking to dump salary. And if they are going to make a serious run at contention, they're probably going to need reinforcements to do so.
The case for selling
There is none. Not unless Baltimore somehow manages to put a lot more distance between the two teams between now and the deadline, which seems unlikely with them playing the Angels and Mariners in that span. Simply put, it's not in the Yankees' business model to waive the white flag on the season when they're that close, least of all in Derek Jeter's final season.
And on a more practical level, the Yankees don't actually have that many assets that would be worth the return to deal. Hiroki Kuroda and David Robertson would interest plenty of teams, but Kuroda has a no trade clause which will limit what the Yankees could ask for him, and Robertson would just be a rental reliever to any acquiring team. Even if a division title is a longshot, it's simply not likely to be worth their while to trade either pitcher.
The case for standing pat
Well...these guys kind of stink. They're as close to fifth place in the division as they are to first, they have the division's worst Pythagorean mark, and let's be honest; it's hard to imagine that even a major addition like Cliff Lee is going to be enough to push this roster into October. What's more, there's a real opportunity cost to making a big acquisition, whether it's the young players you have to give away or future payroll and roster spots. For example, while Lee looks like a very sensible addition now, if picking him up means there's no room and/or money to make a run at Max Scherzer or James Shields in free agency how worthwhile is the move? Especially if the Yankees still come up short of the postseason? The most prudent course might be to go through the dog days with this group, make a few very low cost additions, and let the chips fall where they may.
I'm not gonna lie, I really don't know what the best answer is here. Probably a combination of buying and standing pat, holding out as long as they can to see where they're going to be in a week, then making a move if they still have a shot. I definitely think they should go for it if possible this year though, if only because the near future doesn't look much brighter than this season. None of their veterans are getting any younger, and Tanaka may spend 2015 rehabbing from surgery. If they stay within striking distance, their best bet may be to put the chips in this year's pot and hope the baseball gods want to send The Captain into the sunset in grand fashion.