One of the more infuriating offseason facts of Cubs fandom over the last few years has been the front offices’ absolute refusal to sign a multi-year free agent deal with a position player. It was all about flexibility, you see. Team control was running out on the core, and the Cubs needed to always be prepared to sell if they weren’t competitive at the deadline.
The last non-pitcher the Cubs inked for more than a year was Daniel Descalso, who the team signed for two years and $5 million, with a team option for 2021.