Is Now the Time for the Red Sox to Extend Chris Sale?

After a World Series title, the Red Sox will have plenty of important decisions to make during the offseason.

As it stands, the World Series celebrations have concluded and the Red Sox will now look to defend their crown in the upcoming season. Of course, this all begins with a crucial offseason and the annual GM Meetings.

Boston has a plethora of pending free agents that must be addressed, but will also be tasked with retaining / extending the contracts of existing Sox players. Dave Dombrowski will need to determine, whether or not, he will re-sign Steve Pearce, Nathan Eovaldi, Craig Kimbrel, Joe Kelly, and others due to their current free agent status.

Additionally, the young talent must be retained in the form of Mookie Betts, Andrew Benintendi, Xander Bogaerts, Jackie Bradley Jr. and Chris Sale. The Red Sox ace may be the most intriguing of the bunch, due to the heavy demand of a frontline starting pitcher throughout all of Major League Baseball.

The Argument to Re-Sign Sale Now

The prior season was a bit of an enigma for the Sox ace. He began the season a little slower than anticipated, but rebounded with one of the most dominant stretches that we’ve seen from a starting pitcher. From June 8th to July 27th, Chris Sale posted a 0.75 ERA over 60 innings. He had a 7-2 record throughout the time span and struck out an astonishing 97 hitters.

There was a nagging shoulder injury that even showed up during the postseason, but it’s very clear that Sale is a premium pitcher in this league. At 100% health, there may not be a better pitcher in all of baseball.

At 29 years old, the lefty’s best days are still ahead of him. Sale will become a 2019 UFA and will see incredible interest if he were to hit the open market. The Red Sox have seen the downsides in waiting to re-sign a starter in Jon Lester. Ownership low-balled the ace and ultimately led to him signing in Chicago after rejecting a “hometown discount.” Dave Dombrowski should be wise and use history as a model to pay his ace now.

According to Spotrac, Chris Sale’s market value is approximately 6 years / $189 million. Yes, it’s a large commitment, but it’s possible to see a number over the $200 million mark due to the heavy demand that will be on the horizon if he reaches the open market.

A deal similar to David Price, with an available “Opt Out” clause after a few seasons is likely, but the Red Sox shouldn’t wait to retain the best arm in baseball.

The Argument to Wait

Injury concerns. Those two words sum up any sort of hesitation that may be present within the Red Sox front office.

In his press conference after the World Series, Dave Dombrowski alluded to the fact that the Sox believe Chris Sale is healthy. This news is slightly optimistic as the ace missed a solid amount of time throughout the season and had multiple postseason starts moved back. Personally, there’s reason to believe that the lefty may require a minor operation, as rest didn’t accomplish the ultimate goal and led to decreased velocity.

The front office may balk at committing roughly $200 million to a starter with injury concerns, which may ultimately lead to a decreased offer, or a “wait and see” approach.


Ultimately, it would be wise for the Red Sox to take an aggressive approach and seek a long term deal with the majority of their core, including Chris Sale. The injury concerns are very real, but the risk of losing out on a Sale sweepstakes should strike fear into the mind of Dave Dombrowski.

It’s highly likely to see, if a deal is reached, an opt out clause present for either the team, or the player, to protect themselves.

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About Cody Collins

Red Sox fanatic from Maine. Co-Founder of SoxSphere. Hit us up with a follow and check out @SoxSphere_CC while you're at it!
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