Looking Back, New York Yankees Made Huge Mistake Signing Jacoby Ellsbury Over Robinson Cano

Generally, Brian Cashman is pretty good at his job as the general manager of the New York Yankees. But every now and then, he does make a mistake in judgment.

After the 2013 season, he made a blunder of one that many got on him then, and looking back, three seasons and three years later, it’s an even worse one.

That blunder: choosing to sign Jacoby Ellsbury to a seven-year, $153 million deal and by doing so, passing on the chance to re-sign Robinson Cano.

Now, some might wonder how the two tie in considering Ellsbury is a center fielder and Cano is a second baseman. At the time, the Yankees were in negotiations with Cano and wanted him to accept their seven-year, $175 million offer, which he didn’t. The Yankees were banking on the idea that Cano wouldn’t have any other offers on the table and he’d accept less money later in the winter to come back to them.

And they were wrong on that gamble, as the Seattle Mariners swooped in and overpaid for Cano on a 10-year, $240 million deal. For Cano, he got the 10 years he wanted, but deep down, he wanted to stay in New York, but negotiations stalled between him and the Yankees, so when Seattle came in with that offer, he got overwhelmed into signing that deal.


Just a few days before, the Yankees had made shock waves by pulling Ellsbury away from their rivals, the Boston Red Sox, and signed him to his massive deal, one in which was a gross overpay and one that other teams around baseball likely weren’t paying for him. When the Yankees signed Ellsbury to that deal, it was a signal to the Cano side that they weren’t caving to his negotiations and ultimately, were passing on bringing him back.

At the time, the Yankees likely figured that Rob Refsnyder would develop into a full-time starter and by this point, Cano would either start to break down or shift to another position.

And three years later, Refsnyder never developed into what the Yankees thought he would, as he’s been moved away from second base and has been moved all around the field and Cano has yet to break down. In fact, Cano has only gotten better and put up an MVP-type season for the Mariners in 2016.

At age 33, Cano hit .298 with 39 home runs and 103 RBI for Seattle in one of his finest seasons in the big leagues and finished eighth in the American League MVP voting. Ellsbury, meanwhile, struggled to hit .263 with nine home runs, 56 RBIs and 20 steals.

Now, it’s not exactly fair to compare their numbers directly since Cano is a cleanup hitter and Ellsbury is a leadoff hitter, but because one was passed over for the other, they get compared. On any other team, Ellsbury’s numbers might be decent. But here’s the thing, they already had his production on the team in Brett Gardner and were paying a lot less for Gardner (four years, $52 million).

Right now, the Yankees are in a transition period where they are moving towards playing their younger guys and someone like Cano wouldn’t seem like it would fit into their plans, but remember, Cano was a homegrown Yankee player and ultimately, could have been the leader of this team for several years and well into the end of his career.

But because the Yankees played contract chicken with Cano that winter and felt like no other team would come close to their offer and decided to go with a center fielder who started to wear and break down before their eyes, the Yankees lost here.

Think about this; what would you rather have, an aging Ellsbury who may only get worse as time goes on and possibly more injury prone as he gets older, or Cano, who even if he shifted from second to third base, would still be producing? Try not to think too hard on this one because the answer is pretty simple.


Also, if Cano had made the transition from second to third, there wouldn’t be a need for Chase Headley on the team and he either wouldn’t be here or would already be traded by now; but that’s another story for another day.

Cashman deserves a lot of credit for the work he’s done with the Yankees and in today’s age of baseball, being a general manager for 19 years is hard work. And for all of the criticisms he gets, Cashman has done a terrific job with the Yankees.

But he got this one wrong. Choosing Ellsbury, who may go down as one of the worst free agent contracts ever handed out by the Yankees, over Cano, was a terrible mistake and likely one he’d like to have a do-over on if possible.

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