Brian Cashman should strike early in free agency

With the GM meetings underway in Scottsdale, Arizona, the Major League Baseball offseason is beginning to take shape. General managers have begun to discuss — and in some rare cases, even complete — trades, while the offseason’s biggest event, the opening of free agency, is on the horizon.

Or rather, the traditional biggest event of offseason. The last few years, however, have seen free agency devolve into something of a snorefest, where players languish unemployed until late in the winter, and with many of them signing at less than their expected market value. If they even signed during the winter at all, that is.

With every set of circumstances, however, comes an opportunity for those willing to exploit it, and the Yankees sit in a prime position to do just that.

Any Major League baseball player hitting free agency this season is aware of the slow free agent market that saw players of all skill levels remain unsigned even as pitchers and catchers began to report. Should they be approached by a team in December with a contract that is a bit less than they desired, might they consider jumping at it before it gets withdrawn, just for some security?

Obviously, the top of the market — your Gerrit Cole, Anthony Rendon, and Stephen Strasburg types — will not be affected by any of these concerns. After all, their agents can point to Bryce Harper and Manny Machado, who, despite having to wait until mid-to-late February to sign, nonetheless eclipsed the $300M mark and made out with their hoped-for paydays. The lower tier players, however, ranging from guys like Zack Wheeler and Hyun-Jin Ryu at the top to mid-tier role players like Howie Kendrick and Steve Cishek, may very well be willing to take a lower offer earlier in free agency.

This is where the Yankees ought to jump in.

Now, I’m not saying that the Yankees should avoid the top of the free agent market and instead go for players who might not be willing to sweat out a slow market. Nay, they should be key players in the pursuit of Cole and Strasburg. But truth is, every team enters free agency with more holes than can be filled with one or two star free agents. For the Yankees, it’s uncertainty in pitching depth and a need for a backup catcher and starting center fielder; for the Red Sox, it’s pitching depth; even the 107-win Astros enter the winter needing pitching with half the starting rotation and bullpen hitting free agency (hmm, perhaps there’s a pattern here?). As the market for Gerrit Cole and Stephen Strasburg develops, the Yankees need to be active elsewhere in free agency in order to put the team into the best possible position in April. The simplest way to do so is by acquiring the free agents required to fill holes who are the top of your list.

In this market, the simplest way to do that may just be to strike fast.