​The 2018-19 offseason is a safe space to reflect on recent mistakes you've made, if you're the Red Sox.


After all, the afterglow of a ​World Series win colors everything a bit brighter.


Regardless of how easily they were able to prosper in 2018, the 2016 and 2017 postseasons would've certainly ended differently with one better calculation on Boston's end: there was no excuse to leave ​Jon Lester disillusioned and fleeing to Chicago following the 2014 season. And John Henry finally admitted as much on Monday.

​​If you recall, the Sox lowballed Lester in Spring Training 2014 while basking in the 2013 World Series. Then, somehow, their season snowballed, and Lester was dealt to Oakland midseason (though many expected him to return in free agency).


Instead, the Cubs pulled off a coup, landing Lester on a massive deal that offseason. The rest is history: Boston, while very strong, relied too heavily on David Price and Drew Pomeranz in 2016 and 2017. Meanwhile, Lester captained the Cubs staff from day one, leading them to the NLCS in 2015 and a World Championship with a transcendent 2016. 

He bolstered his Hall of Fame resume by leading a second franchise, and the Sox ultimately found their way to another ring regardless. Still, it would've been very nice if things had turned out differently for a legendary Bostonian who wanted to stay.