Yes, Holliday would make the Yankees better. Maybe a juggernaut, even.
But the only way the Yankees can fall into a habit of losing, someday, is by stockpiling too many players in their 30s with big long-term contracts. It’s incredibly difficult to place a value on flexibility, but that value is real and important and Brian Cashman’s awareness of that value is going to keep the Yankees on top for quite some time.
Now, the issue that we are discussing is not positional flexibility. The Yankees are not leaving left field open because they see a better player to fill that hole on the horizon. As Chris noted this morning, Holliday is likely a better player than Carl Crawford, and I do not see any superior left fielders becoming available in the next few years. As such, it seems clear that the Yankees are doing their best to maintain some semblance of financial flexibility. To do so, it is important to avoid doling out large contracts for players at non-premium positions.
Piecing all of this together, it means that Brian Cashman likely sees left field as a position that he can fill regularly with players on 1 or 2 year contracts, and save the big money for pitchers and players that play premium positions. This is what I mean when I say that the plan in left field is no plan at all. The long term vision of the club does not include a left fielder, and probably does not include a right fielder either. Those players will be added every couple of years on reasonable contracts to fill holes, while the major contracts will be reserved for the Joe Mauer’s and Felix Hernandez’s of the world. As Neyer notes, this is a prudent strategy, and one that should keep the Yankees at the top of the sport for a long time.