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Is Brian Cashman finished for the winter?

Let’s look at Brian Cashman’s track record and try to project whether he is likely to make any more moves.

2019 ALCS Game 3 - Houston Astros v. New York Yankees Photo by Rob Tringali/MLB Photos via Getty Images

The first week of January has come and passed, and most of the big free agents are off the board. We’ve reached the point in the offseason where everybody begins to look towards the day that pitchers and catchers report to spring training more than they look at the hot stove. Yankees fans in particular can refrain from refreshing their Twitter feeds, as the signing of Gerrit Cole and the re-signing of Brett Gardner (although the latter deal is still not yet official) leave most fans content with the roster as currently constructed.

But is the offseason truly over for the Yankees? While a general manager’s job is never completely done, and there are still multiple things that could conceivably be on Cashman’s to-do list — trading J.A. Happ, for instance, or actually getting Gardner on the official roster — we can take a look at the historic data to try and gauge whether or not the Yankees are likely to make a free agent signing the rest of the winter.

The chart below graphs dollar amount of contracts signed by the Yankees over the course of an offseason since the start of the decade, excluding contract extensions but including players who were re-signed after their contracts had been allowed to expire.

With one exception, Brian Cashman has historically done all of his heavy lifting in the month of December — and that one exception, Masahiro Tanaka, was a special case due to the rewriting of the posting system that winter. Other than that, however, Cashman has primarily found role players and relievers in January that he could sign to short-term contracts.

When we compare this to the list of free agents who remain unsigned, we find a few players that may fit these categories: former Red Sox utility-man Brock Holt (projected 2 years, $8M by MLB Trade Rumors), Cameron Maybin (not listed among Top 50 free agents), and Brian Dozier (not listed among Top 50). All three players will likely receive small, short-term deals, although they do not necessarily have clear roles that they would play.

Trades, however, reveal a more interesting dynamic.

As with free agency, Cashman does the bulk of his real work during the month of December, although he is more than willing to break that rule should either a deal fall into his lap (Alex Rodriguez) or a need arise (Vernon Wells). Of note, however, are the dates at which he’s traded away veteran starting pitchers: January 5, January 21, and February 19. For the most part, it appears that he waits until after most starting pitchers have signed before moving any starting pitching depth. This is a trend that we may see continue, as the Yankees have reportedly shopped J.A. Happ this winter but have yet to pull the trigger on a deal.

Of course, it’s impossible to know whether or not this will be one of the years where Cashman sits tight in January and February, or if he will remain active on the free agent and trade markets. Judging from his history, though, it is clear that the types of moves that he makes at this time of year remain on the table.