The Red Sox have a lot of uncertainty surrounding their upcoming free agents. The club’s going to have to make some tough decisions as to which young pieces are worth investing in and which ones are worth moving on from.
There’s not as much uncertainty when it comes to Chris Sale. The left-handed ace is in the final year of his five-year, $32.5 million contract (an absolute steal), which is set to pay him $15 million this season (still a steal).
Sale’s been crystal clear with his preference — he wants to remain a member of the Boston Red Sox.
The team has been crystal clear — it wants the man that was on the mound to clinch the 2018 World Series back for 2020 and beyond.
So shouldn’t this be easy?
Well, we all remember how this same situation went with Jon Lester after winning the 2013 World Series entering a contract year. The Red Sox offered an underwhelming four-year, $70 million extension to him during spring training in 2014. After declining, Boston was forced to trade Lester to the Oakland A’s as a rental piece at the trade deadline. Lester then agreed to a six-year, $155 million deal with the Cubs prior to the 2015 season, leaving Boston’s offer looking laughable, while Lester went on to reverse another curse in Chicago.
Now that the Red Sox have won some hardware of their own since blowing the Lester negations, owner John Henry said as much in his own words to the media down in Florida.
“I think we blew the John Lester [negotiations] … we blew that signing in spring training,” Henry told reporters at a media session that also touched on his presence to sign Sale.
What makes it worse? Lester admitted that he would’ve taken a significant hometown discount to stay in Boston — something in the neighborhood of $120 million over five years, per an interview with WEEI.
So what does this all have to do with Sale?
The Red Sox know they can’t blow this one. Combine that with Sale’s preference to remain in Boston, and this gives Henry, and the rest of ownership, a second chance to make right on how they wronged Lester.
Three of the four highest paid players in baseball from the 2018 season were starting pitchers and will be the comparisons when drawing up a deal for Sale. Below are their full salaries (in order of what they made in 2018).
Clayton Kershaw of the Dodgers is in the midst of a seven-year, $215 million extension. Zack Greinke of the Diamondbacks recently signed a six-year, $206.5 million deal. And, making things more complicated, the Red Sox have the fourth-highest paid player in baseball — David Price, who just opted into the remainder of his seven-year, $217 million deal.
Paying Price and Sale could handcuff Boston in its ability to also re-sign some of the younger position players when the time comes. But the team, through Henry, has admitted to learning from its previous mistake. Signing Sale to a fair extension early could be the best way to budget the payroll long-term, seeing the alternatives with Lester would’ve been giving in too late for full market value, or losing him.
The Red Sox managed Sale last season — the 158 innings pitched were his fewest since he moved from the bullpen to the rotation. However, his 2.11 ERA was the lowest of his career as a starter. And that proved valuable, as Sale was an elite starter in the postseason, and a top option to close when things mattered most.
Given the mutual interest in agreeing to a long-term deal, look for the Red Sox to try and get an extension done with Sale sooner rather than later. For now, Sox fans should feel confident that they’ll see Sale in their uniform for years to come. If that’s not the case by the time Opening Day rolls around, then maybe the Red Sox weren’t exactly being honest about learning their lesson.