In the past two years, the Cardinals have extended Stephen Piscotty, Carlos Martinez, and Paul DeJong to long term deals. Over those same two seasons, the Cubs repeatedly (and unsuccessfully) attempted to similarly extend several of their young core players. Their only recent success was adding a single option year for Pedro Strop.
How to the Cardinals continue to sign their young players to team-friendly extensions, while the Cubs remain unable to do so? Seriously, I’m asking you because I have no freaking clue.
Usually when I present such a question to open a post, I spend the remainder of the post presenting evidence to answer the question.