Would It Be A Smart Move For the Red Sox To Extend Chris Sale This Spring?

Red Sox executive, Tom Werner, made it known that extension talks have begun with Chris Sale. But should the team do it ahead of the season?


While various offices were closed due to President’s Day, giving a chunk of the public the day off from schlepping to work, the Red Sox completed their first full-squad workout. And with the entire organization being present in one area that could only mean one thing–media availability.

The offseason’s been dreadfully slow and the ballclub appears to be entering 2019 with almost the exact same roster as they had in 2018, aside from a few minor adjustments. But one of the main topics as the spring has begun is the team’s future free-agents and who they will be potentially keeping going forward. And Red Sox Principal Owner, John Henry, admitted something today that we kind of already knew. Per the Boston Globe, which Henry also owns, when discussing the impending free agent classes over the next few years, he alluded to the fact that the team will not be able to hold onto all of the core players that the team is lucky enough to have together at this moment.

However, one of the key, relatively recent acquisitions on the Red Sox, Chris Sale, has apparently already had some early talks about a contract extension with the team.

Since being dealt to the Red Sox ahead of the 2017 season, Sale has been exactly who they thought they were getting. The lefty has been as dominant as ever, been the American League’s All-Star starting pitcher each season and has continued his streak of receiving Cy Young votes making it seven consecutive seasons.

Chris Sale wants to be here, he’s already made that clear. He loves the city and the fan base and told the media that his phone’s on if the team is ready to talk. Well, it looks like it rang according to Tom Werner because it appears as though the conversations have already begun.

The question then becomes; would it be a smart move for the Red Sox to extend Sale’s contract and truthfully, pay him what he deserves this spring rather than waiting until next offseason?

The positive aspect of getting this deal done and out of the way now? It doesn’t allow Sale to hit the free-agent market which then seemingly takes away any competition that you will have for the ace. The free-agent market has essentially seen the equivalent to the stock market crashing. There’s no movement anymore and owners are staying pat, but I think it would be different for a guy like Sale.

While he would command a major payday and receive one, he’s made it clear that his first objective is winning. So if the right team comes along with a deal that is even semi-close to worthy of his talents, he’ll take it due to his simple love for the game one would believe.

The con of getting a deal done now? What happens if that shoulder which hindered him in 2018’s sees more issues? What happens if the Red Sox extend Sale on what would be a lucrative deal and it turns out that his left shoulder can’t hold up long-term?

And putting his 2018 injury aside, it’s come to the point where a serious problem for the lefty is his inability to be consistent to end the regular season. For most of his career, he’ll cruise through a majority of the year and essentially have the Cy Young locked up if he continues on a path that’s anything close to how he had been. But as we get into July, August and then September, his shoulder wares out and next thing we know, he doesn’t look anything like the guy who was putting up zeros on the scoreboard in mid to late July.

Chris Sale’s contract will be something interesting to monitor. If they sign him ahead of 2019’s Opening Day ring ceremony, they’re putting a lot of faith in that shoulder staying healthy for years to come.

My personal opinion? You risk the free-agent frenzy for Sale next offseason and hold off until the end of 2019. The injury is something that you need to monitor and if it holds up through the entirety of this upcoming season, do everything you can to sign him. But if it falls apart again, the team then will have to decide whether or not the end of the year blues are worth your payroll extending that much more.

Slowing down at the end of the season, as I said, isn’t anything new for the pitcher.

In 2015, Sale’s ERA from the start of the season until the end of June was 2.87. From the start of July through the beginning of October, he threw a 3.93.

In 2016, his ERA from April to the end of June was 2.79. From the start of July through the end of the season, it was 3.88.

His ERA through the end of July in 2017 topped out at 2.37. His ERA from the start of August through the end of September? 4.09.

This is a three-year sample and yes, he is frequently seen as one of the most dominant pitchers in baseball and I think the Red Sox should and will sign him long-term. If you can smooth out these latter half of the year issues, you have yourself a top pitcher in baseball on the mound every five days. But why rush it and pull the trigger on it this early if realistically, you don’t have to?

With all of this being said, I do see a deal getting done for an extension this spring.

During his presser today, Henry admitted that he thinks the Red Sox “blew” the Jon Lester situation ahead of the 2014 season.

This tells me that Henry is not looking to have another regrettable situation occur when it comes to one of the games best talents. I think the team wants to get this done and taken care of now.

Henry and the team must have this same thought process as the fans do. When the club let Jon Lester walk, they fell into the famous “five aces” season which included Clay Buchholz, I guess, in the aces throne. Sure, this time around you have David Price, but if you lose Chris Sale, your staff’s talent and dominance decreases dramatically.

He’s a veteran on the team and I think his deal getting taken care of now won’t upset other players, such as Mookie Betts and Xander Bogaerts, who are also mulling their impending free agency. At this point in his career, Sale is a well-respected veteran and I think that would keep the attitudes of other players looking for long-term deals in check.

Sale is an all-star, Cy Young candidate each and every season, and World Series Champion. His resume speaks for itself.

In the end, despite fatigue and shoulder injury, Sale deserves a large and lucrative deal. He fits perfectly in the Boston atmosphere, loves the city, the team, and most importantly, winning. Don’t be surprised when you see this deal get done in the coming days.

All statistics pulled from fangraphs.com