The 2018 World Series Champion Boston Red Sox are a very good baseball team who not only walked away with a title, but also the most wins in Major League Baseball. Therefore, if the organization wants to repeat its success, it only makes sense for them to try to keep the roster relatively similar to the powerhouse of a squad that they had in 2018. 

This seems to be what owner John Henry was thinking when he signed Chris Sale to a five-year, $145 million extension one year before his pending free agency. However, not everyone is convinced they needed to jump the gun. Although the lefty was phenomenal last season, boasting a 2.11 ERA with 237 strikeouts (!) in 158 innings, he did show signs of shoulder trouble that some believed would lower his value down the stretch. 

Buster Olney, in particular, believes Boston has made a huge mistake. 

For him, even the slightest possibility of an arm injury is enough to make the Red Sox look silly. He assesses that their fear of having a Jon ​Lester repeat incident (blowing a slam-dunk extension with a low offer) clouded their judgment in negotiating with the southpaw. But is this not a rational fear? Boston low-balled Lester in his prime, sending him to Chicago, where he would eventually seal the club's first World Series victory in over one hundred years while the Red Sox floundered in October, short-staffed...until Sale arrived.

John Henry is taking the safe route, the path that he should have taken in 2014. The details of the injury are not well-known to those outside the walls of the Boston clubhouse, and to make the same mistake twice would not sit well with the fiery fans of Fenway. 

The organization seems to be one hundred percent satisfied in their decision, as their pinned tweet features the deal:

On the Red Sox twitter page, their bio reads, "Official Twitter of the 2018 World Series Champions. We wanna do it again." And, although Buster Olney sees it is a mistake, Boston believes that to do it again, they need ​Sale on the mound. For a while.

Damn the possible costs down the line.