Things are heating up in Spring Training as the Red Sox are preparing to defend their world championship. One key piece to defending the crown will be re-signing key players to new deals.
We all know that after this season lefthanded ace Chris Sale will be on the free agent market. That is unless the Red Sox and Sale are able to come to an agreement beforehand. Sale will be just one of several big possible free agents for the Red Sox in the upcoming years. This isn’t the first time that Boston finds themselves in this position.
During a media event at the Red Sox training facility in Fort Myers Principal Owner John Henry admitted that Sale’s soon to be free agency felt familiar. The situation that he is referring to is that of former Red Sox star Jon Lester. Boston lowballed him prior to 2014 and then sent him to Oakland during the trade window. Lester would become a free agent going into 2015 and he’d land a massive 6-year $155M contract will the Cubs.
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At the time Henry had a self-imposed policy that he didn’t want to tether the team to a pitcher 30 years or older. Since that mandate, the Red Sox have signed David Price who is now above that threshold and have eyes on retaining Sale who is 29. So some things have changed and it seems that age is but a number to the Red Sox.
"“I think we blew the Jon Lester — we blew the signing in spring training,” Henry said. “And for reasons that are pretty apparent now, which I won’t go into, but they’re apparent. But it wasn’t… you can see what’s gone on in free agency. The price of WAR has gone up radically that it’s difficult, whether it’s a pitcher or a position player, entering into a really long term contract with high dollars.”"
It’s clear that even years later, Henry seems for a lack of a better term, bothered, by losing Lester. Jon had come up through the system and achieved great things with the Red Sox. Sadly, some poor business moves severed that relationship and in a time when Boston needed pitching most.
So it looks like when the contracts start expiring on the current crop of Boston stars, Henry and Fenway Sports Group will be doing whatever they need to in order to keep the squad intact. The current ice-cold climate of the free agent market will also play a factor. Possibly in the Red Sox favor.
"“So he’s a special player. We would love to be able to sign him. I think he would like to as well. But there are the realities of the marketplace in budgets and this is his opportunity to be a free agent, so, potentially … something could happen.”"
I wouldn’t be shocked if players begin signing extensions before their deals come due at the end of the season. If the market just isn’t there like it used to be then there aren’t many other options. This could mean great things for the Red Sox as they’re going to have to spend and spend big in the near future. Henry definitely has his sights set on re-signing Sale and there seems to be some urgency in his words as well.
The Red Sox will have to make some big decisions and make them quick. With a crop of guys set to become free agents at the season’s end and more coming in 2021, it may be time to start wheelin’ and dealin’. I think Henry sees that and he doesn’t want another Lester situation on is hands.