Did the Red Sox make a mistake when they extended Chris Sale?

FORT MYERS, FLORIDA - FEBRUARY 17: Chris Sale #41 of the Boston Red Sox throws a bullpen session during a team workout at jetBlue Park at Fenway South on February 17, 2020 in Fort Myers, Florida. (Photo by Michael Reaves/Getty Images)
FORT MYERS, FLORIDA - FEBRUARY 17: Chris Sale #41 of the Boston Red Sox throws a bullpen session during a team workout at jetBlue Park at Fenway South on February 17, 2020 in Fort Myers, Florida. (Photo by Michael Reaves/Getty Images) /

Chris Sale begins the first year of a contract extension he signed with the Red Sox. Based on injury concerns, it’s fair to ask if it was a mistake.

Right now looking toward the 2020 season, the Red Sox starting rotation is in complete shambles. The departures of Rick Porcello and David Price reduced the Boston rotation to Chris Sale, Eduardo Rodriguez, and Nathan Eovaldi.

While the team did sign Martin Perez to a one-year deal and he looks like he’d be the obvious candidate for the fourth starter, the Red Sox currently head toward Opening Day with only three legitimate major league starting pitchers.

Of the three remaining Red Sox pitchers, all are injury risks as Sale and Eovaldi have battled injuries the last few years as has Rodriguez. Although the latter was able to stay healthy throughout 2019 en route to the best season of his career. However, while Rodriguez was Boston’s best pitcher in 2019 and looks to build on it heading into 2020, there is no doubt that Sale is the team’s undisputed ace.

That is when he can stay healthy. This season will be Sale’s fourth with the Red Sox, but his first under the new contract extension he signed in 2019. Heading into last season hot on the heels of the team’s World Series win in 2018, Sale was in the last year of his contract and due to be a free agent at the end of 2019.

While he’d for the most part been fantastic for the Red Sox, there was some concern that it might not be a good idea to extend him.

For one, he had broken down in each of the last two seasons in Boston. In 2017 he seemed to just run out of gas by season’s end and in 2018 he battled nagging injuries late in the summer and had his workload severely reduced heading into the postseason. While he still pitched effectively that October, it was obvious to anyone who had seen him pitch earlier that season that he wasn’t the same.

Sale’s workload, among other reasons, was the impetus for former manager Alex Cora to go easy on the team (especially the pitchers) in spring training last year. For Sale, it didn’t seem to matter as his velocity was down and his effectiveness diminished right out of the gate. Still, right before the season in late March 2019, the Red Sox and Sale agreed to a five-year extension worth $145 million. Both the team and Sale seemed happy with it, but not everyone was.

At the time, I and many others thought that the Red Sox had jumped the gun in extending Sale. Even though he was one of the top pitchers in the American League, he had finished the last two seasons poorly and was about to turn 30. With his slight build, unorthodox throwing motion, and the fact that most pitchers begin to decline in their 30s, it seemed like the Red Sox should have waited to see how Sale pitched in 2019.

Indeed, my preference heading into the season, even before they announced the extension, was for the Red Sox to not sign Sale and to assess how well he was pitching by the All-Star break. If he looked fantastic, they could go ahead and sign him; if he was struggling or injured, then they could decide to either let him go at the end of the season or sign him, but at a reduced rate since his stock would be down.

Instead, they pulled the trigger before the season even started and now it looks like it may have been a mistake.

Last season was Sale’s worst in a Red Sox uniform: he finished with a 6-11 record with an ERA of 4.40. While he did have 218 strikeouts and only walked 37, he only pitched 147.1 innings before being shut down in August for arm soreness. His season was strange because he started slowly with decreased velocity and not much movement on his pitches.

He was also hurt by poor run support in several starts (who can forget the back-to-back starts in which he whiffed a combined 31 batters…and lost both?).

Paradoxically, and rather cruelly at that, he finally looked like the real Chris Sale in his last few starts when he was touching the mid-90s with his fastball and his stuff looked great. Then, suddenly the team announced that he would be done for the season due to an issue with his pitching arm.

Initially, there was speculation he’d be back in time for the postseason (if the Red Sox made it) before the team shut him down completely. He wasn’t cleared to start throwing again until late in the winter and Red Sox fans hoped he’d be back to full strength by spring training.

Instead, it seems to be more of the same though no fault of his own. Sale arrived in Ft. Myers with a nasty case of the flu which had turned into pneumonia. Because of this, the team announced earlier this week that Sale will miss the first two weeks of the regular season on the 15-day IL.

Sale and the team explained it by saying that since he’d miss a couple of weeks worth of work in spring training, he’d need to make those up during the beginning of the season.

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While it’s not particularly ominous and Sale’s health should be fine by the time he makes his season debut, in the bigger picture it’s not a great way for the first year of the extension to begin. He’ll be 31 right after the season starts and hasn’t finished a full season strongly in three years. Pitchers usually start their declines in their thirties and with as hard as he throws and his unusual mechanics, there’s no telling how much more Sale and his arm have left in them.

None of this is meant to disparage Sale as either a person or a pitcher. He seems like a good guy and a great teammate and when he’s dialed in, he’s one of the best pitchers in the league. However, his health concerns and career longevity are real issues and it’s looking more and more like former President of Baseball Ops Dave Dombrowski extended Sale prematurely and unwisely.

What hurts, even more, is that along with several other bad contracts the Red Sox handed out in recent years, most notably to Nathan Eovaldi, Sale’s extension and the commitment to pay him for the next five years contributed to the payroll bind the team was in where they felt they had no choice but to trade Mookie Betts for pennies on the dollar.

I wish for nothing more than Chris Sale to get (and stay) healthy and return to being the dominating pitcher we saw for most of 2017 and 2018.

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However, based on what I’ve seen the last few seasons and where the team currently is based on decisions that were made, right now it looks like the Red Sox made a big mistake in extending Chris Sale. This season will be the first of five seasons under that contract so we’ll see starting in a month whether that ultimately proves to be the case.