Red Sox: Chris Sale’s pending opt-out raises contract questions

BOSTON, MA - SEPTEMBER 17: Chris Sale #41 of the Boston Red Sox pitches in the second inning of a game against the Baltimore Orioles at Fenway Park on September 17, 2021 in Boston, Massachusetts. (Photo by Adam Glanzman/Getty Images)
BOSTON, MA - SEPTEMBER 17: Chris Sale #41 of the Boston Red Sox pitches in the second inning of a game against the Baltimore Orioles at Fenway Park on September 17, 2021 in Boston, Massachusetts. (Photo by Adam Glanzman/Getty Images) /

Did the Red Sox make a mistake with Chris Sale’s contract?

The MLB imposed deadline for the new CBA is fast approaching and while players are getting in some work on their own time, nothing will compare to being able to use team facilities. For the Red Sox, their efforts are being led by Chris Sale as he’s been able to open up the doors to his Alma Mater to get his guys ready for 2022.

The season isn’t all Sale must think about in 2022 though as he has a big contract opt-out coming as soon as the final out is made. Much like J.D. Martinez and even more so Xander Bogaerts, who also has an opt-out after this season, The Condor has a big decision to make. Stay with the Red Sox, who have seen the highest of highs and lowest of lows during his time here, or pack his bags and head elsewhere.

When I started thinking about the possibility of Sale leaving after this season I decided to take a deeper look at his contract and decide if the cash Dave Dombrowski splashed has been worth it or not. It’s a tough decision to make as I’ll be taking a look at both the actual numbers while also factoring in subjective opinion.

Dombrowski signed Sale to a contract extension in March of 2019 and his new deal wouldn’t go into effect until 2020. A fresh 5-year/$145M deal and a new outlook on his future with the Red Sox would motivate the newly minted World Series champion as the regular season approached. The Boogeyman was coming off of a season that saw him battle injuries as the Fall Classic approached, still, he had earned every penny coming to him.

His elbow and shoulder would plague him as 2018 came to a close with a mystery stomach ailment mixed in during the Postseason. He was the heavy favorite to win the Cy Young that year until he missed a majority of the second half thanks to those issues. The southpaw went into 2019 reportedly healthy and ready to rock and prove to the baseball world that he was still the menace we knew him to be.

Unfortunately for everyone involved, the Red Sox stumbled massively out of the gates and never got going in their championship defense. They would finish fourth from the bottom of the league and Sale would miss over a month of time once again due to his elbow. Anyone watching him pitch knew something was off and even at times when he was healthy it didn’t seem right.

I had heard more than a few times that his style of pitching would ultimately be more of a when and not an if in regards to Tommy John, and that thought became a reality in 2020. The lefty tried to get his arm right by any means not related to surgery but after setbacks and speed bumps, it was inevitable and he went under the knife.

We wouldn’t see him take the mound for the Red Sox again until the summer of 2021 in front of a jam-packed Fenway Park, and he looked like his old self. Sale would finish the season with a 5-1 record, 3.16 ERA, and a 4.33 SO/W mix. He would also pitch the game of his life in the Postseason but the Red Sox offense couldn’t find their way to reward him for his efforts.

Now that we’ve done the walk down memory lane it’s time to look at the numbers. Since signing his extension on March 22, 2019, the veteran has spent a total of 254 days on the IL between his elbow, shoulder, and eventually Tommy John. He also missed a week of time due to COVID in 2021 just to add a miserable cherry to the setback sundae.

In those 254 days, he has earned a whopping $37.4M all while not being able to take the ball. Obviously, that’s the way the world works and you can’t predict an injury, but we should go back to the overarching contract terms when eyeballing his stays on the IL. When he signed his deal he was one of the best pitchers in all of baseball but he was entering his age 30 season and had just missed a month of time when the Red Sox needed him the most in 2018.

As I was combing through the contract terms nothing really stood out to me until I got to a section that until today I actually didn’t know about. Mixed in with all of the usual bonuses and escalators for awards and performance is a line about deferred years. We all love to make fun of the Mets for Bobby Bonilla but Sale’s contract may take the cake. His deal has $50M deferred at $10M/year between 2035-2039.

That’s right, well beyond his playing years he’ll be cashing massive checks from John Henry and the fellas. Again, I’ll never begrudge a player for getting the best deal humanly possible for them and their family but Dealin’ Dave really got loose with this one. Deferring money is common practice in contracts like Sale’s but $50M that far down the road for a guy who will be long retired is mind-boggling to me.

The other thing that Dombro did that had me scratching my head at the time was the actual extension itself. We didn’t have to worry about inking him to another deal until after the 2019 season but the former President of Baseball Ops jumped the gun before it was necessary. Had he waited then things may look different as far as the contract is concerned. Then again Dombrowski wasn’t long for the Red Sox world so it doesn’t really matter.

The lefty deserved the extension and has been a driving force in Boston even when he’s not on the mound, but the structure, size, and amount of his contract are easy to question. While I’d much rather have him in our uniform than that of another team, I think a different route with the terms could’ve been taken and the Red Sox could’ve saved some cash in the long run. With three years left to make his mark, I wouldn’t be surprised to see him go into full assassin mode.

Boston has a problem in the not-so-distant future with key players in their system being able to walk when this coming season concludes. During one of the recent workouts at FGCU, Sale was heard saying he wasn’t going anywhere, which should be reassuring. When they’re allowed to meet again, I hope he and Chaim Bloom sit down and the two can map out the future and the plans both have regarding the team. If the Red Sox want another banner at Fenway Park, they’ll surely need Chris Sale to help them get it.

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