The Cubs’ biggest – and only! – multiyear free agent signing on the position player side in the last five years was Daniel Descalso, whom they inked to a two-year, $5 million deal in December 2018. Before Descalso, it was Jason Heyward in December of 2015. So Descalso holds a pretty unique spot in Cubs lore, even if his signing ultimately did not work out.
… not even a little bit. Descalso wound up playing 82 games with the Cubs over those two seasons, most of them while injured, and his production was non-existent. It’s not his fault the Cubs have signed no other multi-year positional guys the last half decade, though.