Robinson Cano
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Brian Cashman has one of the best resumes of current general managers in the league. But he might have one blip on his resume in Robinson Cano.

Four years ago, the New York Yankees had a chance to re-sign their All-Star second baseman and not only keep him long-term, but make him the face of the franchise. Due to the influence of Jay-Z and Roc Nation, Cano opted to chase for the bigger contract and signed a 10-year, $240 million deal with the Seattle Mariners. The Yankees final offer: seven years and $175 million.

Granted, the Yankees didn’t want to outbid themselves like they did in the CC Sabathia negotiations of 2008. But their unwillingness to pay, and to a point, overpay, to keep their best player at times, has come back to bite them.

Up until they had landed Starlin Castro from the Chicago Cubs in a trade two winters ago, the Yankees were parading a who’s who of bad second base options. Brian Roberts, who eventually got released. Stephen Drew, who struggled to hit .200. Ron Refsnyder, who was so bad, it forced the trade for Castro. Dustin Ackley, who couldn’t stay healthy. And then Castro, who has played tremendously and was even voted to the 2017 All-Star team and replaced by Robinson Cano because of an injury.

Cano, whose now in the fourth year with the Mariners, is having another All-Star season in Seattle and just won the 2017 MLB All-Star Game MVP Award after he hit the go-ahead home run in the game on Tuesday night in Miami.

Now the player the Yankees chose to sign instead of Cano; Jacoby Ellsbury hasn’t made a single All-Star appearance. Instead, it’s been a lot of injuries and disappointments for the veteran outfielder that the Yankees shelled out seven years and $153 million to. Money that really should have gone to Cano but didn’t because the Yankees were tired of playing contract chicken with Cano and Jay-Z, who was emphatic on getting 10 years.

In hindsight though, Cano has since admitted that he wishes he stayed in New York and with the Yankees. But the Yankees have at least found someone decent enough to play second base in Castro, although he is a converted shortstop that learned to play another position and who knows if he even sticks permanently at second base.

However, Castro isn’t on the same level as Cano, who at times, is an MVP candidate in the American League and has done his best to try and carry Seattle, but hasn’t had the kind of teams around him like he did with the Yankees.

And for all we know, Cano may never win a title with the Mariners. He did get his contract with the Mariners though. And he still continues to put up tremendous numbers; numbers that he could be putting up with the Yankees had they not decided to get stubborn and pay other team’s superstars over their own.

For every All-Star and MVP type season that Robinson Cano has, the Yankees have to watch and wonder what could have been.

Instead of overpaying for an injury-riddled Jacoby Ellsbury, they could have retained Robinson Cano. It’s one of the few blunders on Brian Cashman’s impressive resume. And on Tuesday night, it was a cold, hard reminder of that “what if.”

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