Is It Time to Approach Jacoby Ellsbury About a Contract Extension?

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Is It Time to Approach Jacoby Ellsbury About a Contract Extension?
Kim Klement-USA TODAY Sports
Can the Sox get a deal done with Jacoby Ellsbury?

The Boston Red Sox might be smart to approach Jacoby Ellsbury and his agent Scott Boras about a contract extension right now given what has happened in MLB this past week combined with the events of this past winter.

Most recently, Boras was just fired by Robinson Cano, who replaced him with Jay-Z. Cano, if he hits free agency and doesn't re-sign with the New York Yankees, will likely be the next $200 million player in baseball. It has to be a huge blow to Boras' ego that Cano fired him on the verge of a huge payday costing Boras millions.

The other key item recently was shortstop Elvis Andrus signing a $120 million contract extension to keep him with the Texas Rangers long-term. The fact that Boras was willing to get a contract done now for the 24-year-old Andrus speaks volumes to where the market is right now.

Ellsbury might be open to the security of taking a six-or-seven year contract that might get him close to $100 million dollars and not risk the issues that faced most of Boras' clients this past winter. A contract extension would also protect Ellsbury in the event of an injury.

Rightly or wrongly, it certainly seemed like Boras misjudged the market this past winter, initially expecting Michael Bourn to get a $100 million payday. Instead, Bourn was a free agent well into February and had to settle for $48 million from the Cleveland Indians.

Another one of Boras' clients that was hurt by free agency was Kyle Lohse. The 33-year-old Lohse was coming off a season where he went 16-3 with a 2.86 ERA and finished seventh in the NL Cy Young voting. Still, Lohse was on the market until March 25th and settled for a three-year contract for $33 million. Hardly what was on the forecast at the beginning of the winter.

Should the Sox try to get a deal done now?

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Teams are holding onto their draft picks now, unwilling to give them up quickly as compensation. That compensation is causing teams to be reluctant to sign free agents. If Cano re-signs with the Yankees during this season, Ellsbury would be the biggest available free-agent after this season.

Using Andrus and Bourn's contracts as a guide, the Red Sox could offer Ellsbury something in the neighborhood of a six-year contract for roughly $100 million dollars and add a couple of team options to the deal in order to allow Boras to sell it as a potential eight-year deal worth $130 million or so.

Teams are signing their own stars, not letting them get to free agency, something that I noted here. It is a sea change for baseball and it might make Ellsbury and Boras more receptive to getting a deal done.

There is risk for the Red Sox here, mainly Ellsbury's ability to stay healthy long-term. If the Sox feel they can manage Ellsbury's health with a move to left field next season, then maybe they can make this work.

Information used from Baseball Reference, Ken Rosenthal/Fox Sports, Wikipedia, Jon Heyman/CBS Sports

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