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Friday, March 22, 2019

Examining Chris Sale’s Contract Extension with the Boston Red Sox

As the 2019 Major League Baseball regular season rapidly approaches, the Boston Red Sox and their star left-handed pitcher Chris Sale, have reached a reported five-year, $145 million extension. This deal will be tacked on to the final year of his current contract and lock keep the ace in Beantown through the 2024 season.

Although the extension has not yet been formally announced, the breaking news does bring some interesting thoughts and questions to mind.

Just this past week, it was reported by Mike Dowling of Forbes that Sale was on the verge of a $245 million extension with Boston. Where did that extra $100 million go? Presumably, the story would not have been released with some sort of credible source to back it up. $145 million is a ton of money, but does seem to be quite a bit less than what most expected the pitcher would get once both sides decided to pull their chairs up to the negotiating table.

Despite the current depressed free agent market, unless there are factors that the general public are unaware of, it seems possible that Sale is leaving quite a bit of money on the table. He has finished at least sixth in Cy Young voting each of the past seven seasons, and at 29 is one of the top handful of pitchers in baseball. However, his new deal is significantly lower on total value and average annual value than the six-year, $203 million pact Zack Greinke signed with the Arizona Diamondbacks prior to the 2016 season. Not only was Greinke 32 at the time, his career numbers, while excellent, are a notch below the value Sale has provided during his career. Marquee free agents typically seek to set standards, not fall well below them.

Sale’s decision to accept an extension now indicates that he may not have felt comfortable  he would have been able to make more on the open market. It is of course possible that he also prefers to remain in Boston for professional and/or personal reasons, but it would have been very reasonable to use Greinke as a comparison when shopping his services. The difference between S203 million and $145 million, and between $35 million annually and $29 million annually are significant. What gives?

Does the Sale extension indicate an increasing unlikelihood that the Red Sox will keep fellow starting pitcher Rick Porcello when he comes a free agent after the upcoming season? With Boston paying starters Sale and David Price around $60 million per year through 2022 (when Price’s deal expires), and the $17 million a year Nathan Eovaldi will make through 2022, how many more big bucks will they want to invest in the rotation?

Price and Sale are obviously extremely talented pitchers, who have contributed greatly to the team’s recent success. However, they have both experienced injury issues in the past couple of years. As they get older and are making $60 million annually between them, it would be catastrophic if one of them went down for an extended period of time, much less both of them. Don’t even mention that Eovaldi just returned from his second Tommy John surgery this past year.

If Sale’s deal is in fact a bit of a “bargain,” does that make the Red Sox feel more comfortable in opening their wallet a little wider when the time comes to pay outfielder Mookie Betts, who will be eligible for free agency after the 2020 season? He has recently said that he does not plan on signing an extension before free agency hits, which means that he is planning (rightly so) to get paid. With Anaheim Angels star outfielder Mike Trout recently signing a mammoth $430 million contract, the Red Sox could use whatever savings they can find in other places to ensure they feel comfortable coming in with a comparable offer to Betts when the time comes.

There will always be questions and thoughts, but for the time being Boston fans should be happy that the team was able to agree to terms to keep one of the best pitchers in their history for years to come

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