For just the second time since the 1994 strike, the New York Yankees  missed the playoffs, and as you’d expect, they’re not taking that setback lightly.
ESPN New York’s Andrew Marchand reported that the Yankees are considering a $300 million spending spree  this winter to put the team back into contention, while still planning to stay below the $189 million luxury tax threshold they’ve been working to avoid for years. The last time the Yankees did that, they followed up their 2008 playoff miss with a $423 million offseason run that brought them A.J. Burnett , CC Sabathia  and Mark Teixeira  — and helped them win the 2009 World Series.
Of course, part of the reason they’re in the situation they are today is because of that 2009 spree. Those three players cost them $64.5 million this year (including the portion of Burnett’s contract they’re paying for him to pitch in Pittsburgh) and brought them just 2.5Wins Above Replacement , with Teixeira injured and Sabathia declining. Still, in the short term, that helped them to a championship, and the hope is that they can do it again.
But while $300 million is certainly an impressive number, is it actually enough to propel the Yankees back to glory? Probably not.
Misleading dollar amount
To start with, let’s stop saying “$300 million” as though it will all immediately affect the 2014 team. When the team went on that 2009 spending binge, the deals signed covered a period of 20 contract years, with approximately $32 million of that actually hitting the books in the first year. (And, it should be noted, team payroll was actually down slightly from 2008 after the expiration of huge deals for Jason Giambi  and others.)
With the team’s apparent insistence on staying under $189 million (really about $177 million, since administrative costs like player health insurance and worker’s comp count against the cap), there’s only so much room to add new talent considering what they already have committed.
Currently, the Yankees have approximately $100 million allocated to Sabathia, Teixeira, Alex Rodriguez ,Derek Jeter , Ichiro Suzuki , Alfonso Soriano  and Vernon Wells , assuming Jeter returns from a lost season to exercise his $8 million player option. (For the purposes of the luxury tax, MLB uses the average annual value of each contract, the sum of which comes to $100 million for those seven players. That is not necessarily what they earn in that year.)
As a whole, this group contributed just 4.5 WAR for the season, or basically what Jason Kipnis  gave Cleveland on his own, and even that dollar figure might be light because it doesn’t include taxable performance bonuses like the $6 million Rodriguez would get for hitting 16 more home runs to reach 660 for his career.
Let’s estimate the money needed for rookies and lesser 40-man roster players at around $5 million, and make it $105 million so far. At this point, the Yankees have $72 million left to play with, and you can probably see where this is going. Without yet adding any new players, replacing Andy Pettitte , Hiroki Kuroda , Curtis Granderson  and Mariano Rivera , or even accounting for arbitration cases like Brett Gardner  and Ivan Nova , the payroll is largely ticketed for a group that consists of one aging starting pitcher, as well as three infielders and three outfielders well past their primes.
If we assume that Gardner, Nova and fellow arbitration case David Roberts on return at around $12 million total, and Cano returns as part of the shopping surge at something like $25 million annually, that’s another $37 million on the books, yet even that is problematic. All four are quality players who can help the Yankees win, but the team will have merely maintained some of last year’s status quo, not improved anything. That is, Cano made $15 million in 2013, and he’s now in line for a substantial raise, yet he’s not expected to substantially increase his already-excellent play to match.
The A-Rod factor 
Rodriguez’s status is, of course, the huge question mark here, since he may or may not be suspended for the entire season, saving the Yankees the pro-rated portion of his salary. The best guess at this point is that he’ll rightfully win his appeal and not be forced to serve the 211 games MLB is trying to impose, but that he will certainly sit out at least 50 or 100 games, which will recoup some savings for the team.
However, it may be another month or more before his situation is clarified, which makes it difficult for the Yankees to plan around, and of course if he’s gone, the team then needs to find another third base option in a painfully thin market.
The numbers we’ve tossed out so far are high-level and may not be accurate to the penny, because an in-depth examination of the contracts and the rules of the salary cap and luxury tax would require far more than this space allows for. But they’re in the right range, and you can already see the problem here, can’t you? A team in an exceptionally tough division that miraculously won 85 games in 2013 — “miraculously” because they were outscored by 21 runs, and were under .500 from early June through the end of the season — is being weighed down on one end by an old and expensive core, and limited on the other by the insistence of adhering to a luxury-tax limit New York could easily afford to exceed.
So sure, the Yankees could gamble on Japanese import Masahiro Tanaka to join the rotation, or add the aging (yet still productive) Carlos Beltran  to the outfield, or make a risky bet on catcher Brian McCann  — or even all three. To do so would add something in the neighborhood of $45 million in salary (Tanaka’s posting fee would not count against the luxury tax), and would basically max out the remaining available payroll. It also leaves them perhaps two pitchers short of a rotation (depending on what free agent Kuroda does), light in the bullpen and without any sort of adequate backup plans for the multitude of risks Teixeira, Jeter and Rodriguez offer in the infield.
For this plan to work, the team would need an influx of talent from the minors to make an immediate impact, but the Yankees don’t have the kind of prospects on the horizon who can be expected to make a difference in 2014.
The Yankees can improve their team this winter, and they can also stay under the cap limit. It’s just going to be very hard to do both, and unless Sabathia, Teixeira and Jeter suddenly look like they did five years ago, the Yankees might not be able to spend their way out of this hole any time soon.