Yankeeland is a pretty conflicted place these days, and I think this is why: They're tweeners. Neither direction really works for the Yankees, because they're in-between: they're not a contender right now; yet they lack many big-improvement moves to pursue; yet they're just good enough to avoid a rebuilding project that might not work anyway. The roster right now isn't good enough to win, and other than signing Max Scherzer for a huge seven-year contract that will look bad before there's still $100 million left on it, there isn't any big improvement to be found.
(2) Major offense improvements are tough to find because five regulars have immovable contracts producing at likely the 1-3 WAR level (McCann, Teixeira, Beltran, Ellsbury, and A-Rod - who may not be a regular, but the point remains that they feel compelled to keep a spot for him).
(3) Sure, some team may trade a star, but it would (a) at best want 1-3 of their relatively few quality prospects, or (b) at worst turn down Cashman for a team with better farm offerings.
But they're not bad enough to tear it down and rebuild, and even if they were, they don't exactly have a Tulo to trade for multiple top prospects. And here's why I'm a little optimistic about what 2015 might still become. They were an average team: they had 84 wins, though they gave up more runs than they scored, so they might really be worse than that. But there's a very plausible path to being 8-10 wins better than last year – just by (1) replacing the substantial time they gave replacement-level folk in 2014, and (2) not suffering an unprecedented level of SP injuries. Add a few more wins from SP improvements, and you may well have a contender.
(1) On offense: Both middle infield positions suffered replacement-level play all year, so each position can rise by 2 WAR this year with Didi Gregorious (who despite weak offense averaged 2 WAR per full season in 2012 and 2013 – which is 2 more than Jeter provided in 2014) and Martin Prado (or a rookie who performs well enough to shift Prado to 3B or a super-sub role). Kelly Johnson played 3B (and a little 1B) in nearly 40% of the team's games, while Zelous Wheeler played another 10% at 3B; they can avoid that half-season of replacement-level play if either A-Rod plays at least some 3B while hitting at least league-average, or Headley fills in for Mark Teixeira at 1B while Prado or A-Rod fills in at 3B. In short, they played so many replacement-level warm bodies in 2014 that just by adding depth – a full season of Prado and Headley, plus whatever A-Rod has to offer, plus just one of Rob Refsnyder/Jose Pirela playing well enough to free up Prado to fill in elsewhere – they can add 4-5 wins easily: 2 replacing Jeter at SS, 1 replacing the Johnson/Wheeler 3B half-season, 1 replacing the Brian Roberts 2B half-season, and 1 at the 1B/3B/RF backup spots that should see a fair bit of playing time.
(2) On the mound: The bullpen shouldn't be worse, and the rotation easily could be better with fewer injuries. You can't assume no starters will get hurt, but 2014's starter injuries were the sort of step-on-a-rake-repeatedly bad luck you can't expect to recur; they should get much more than last year's 0% of a C.C. Sabathia season, (basically) 0% of Ivan Nova, 40% of Michael Pineda, 60% of Masahiro Tanaka, and 75% of David Phelps. They could pick up several additional wins in the not-even-best-case scenario of, say, 2/3 of a decent Nova season plus either (not even both) of Pineda or Tanaka pitching a full season. To be sure, Brandon McCarthy plus Shane Greene equaled about 85% of one solid season they could replace with a mid-market SP, and Kuroda need to be re-signed or replaced – but those aren't tall orders.
Which is to say: It's all about the SP now. The bullpen is set and they'll have done as much as they can for the offense if they land Headley – and I personally prefer leaving Prado/A-Rod at 3B to give 2B to a Refsnyder/Pirela competition, because successful teams give chances to kids who've earned it. So all I'm really watching now in the baseball news what SP they still can land (a) to replace Kuroda and McCarthy/Greene and (b) to make up for the fact that they've hit a limit in their ability to improve the offense.
Going big on SP is the last way they can infuse some more wins into a team that may be on the bubble of contention, but that sure could use some more reinforcements – and every quality SP who goes off the board (Lester, McCarthy, Santana…) is one less chance to go big on SP. I'm not optimistic that they'll land the Scherzer or Shields they need - but I am optimistic that if they do, that really could be the final piece they need to contend.