The free-agency compensation system in MLB is hilariously broken. Designed by the owners as a means of capping the top end of the free-agent market, but plugged as a way to keep small-market teams from losing star talent to free agency without any consolation prize, the structure no longer does either. Teams are best served by being aggressive in free agency, and in a perfect world, they cluster additions and go get other people’s players, rather than retain their own.

So it stands for the New York Yankees. They signed Brian McCann, the premier free-agent catcher, to a five-year deal on Saturday, thus giving up the 18th pick in the 2014 First Year Player Draft. They’re also keeping an open dialogue with Robinson Cano, the best free-agent anything this winter, and an incumbent Yankee. Meanwhile, they seem perfectly content to let outfielder Curtis Granderson and starting pitcher Hiroki Kuroda depart for some other team, and collect the draft pick to which they’re entitled if that happens.

Right now, the best thing the Yankees could do is move on from Cano. They should spend whatever it takes to add Masahiro Tanaka, the Japanese starting pitcher with ace upside who will be posted for bidding by MLB clubs later this winter. They should look at Omar Infanta, and perhaps Shin-Soo Choo or Stephen Drew.

That’s because, with McCann on board and their first draft pick gone, the Yankees still have a chance to come out ahead when it comes to the draft, by spending aggressively on outside free agents. The 18th pick is gone. The next one the Yankees would lose by signing a top-end guy would be, roughly speaking, the 55th. The one after that would be the 90th, or so. If the Yankees held off, though, and let Cano, Granderson and Kuroda sign elsewhere, they will end up with three picks in the 30-40 range. Given not only the historical talent levels at those spots, but also the money assigned to each draft slot under the new CBA, the three clumped picks are preferable even to having kept the 18th, and having the others.

Cano is obviously more valuable than a draft pick at the end of the first round, even on a fairly lucrative contract, but:

  1. The Yankees are old, and have a mediocre farm system, and whereas keeping Cano would exacerbate each problem, letting him go would help ameliorate each problem; and
  2. The next-best alternatives to Cano—be it Infante (a free agent) or Brandon Phillips (a trade target that would cost virtually no talent, given his bad contract)—soften the prospective blow of losing even a superstar second baseman. Besides, second basemen age poorly.

Expectations and ownership pressure will always compel the Yankees to field as competitive a big-league team as they can. If GM Brian Cashman wants to build a viable long-term contender, though, he needs to attack the problem of the team’s age and inflexibility, and these are the little ways in which he can do that.

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