2. Jason Heyward
Despite Heyward’s status as a Gold Glove candidate nearly every season, his salary doesn’t back up his slumping bat. Heyward bat just .265 in 2020, which was actually an improvement on his .251 designation the year prior. Chicago can get the sort of offensive production from a mid-tier free agent outfielder, or could even splurge for the likes of Michael Brantley, who’d be a significant upgrade at the plate from Heyward.
So what’s stopping this from happening? Well, it’s Heyward’s contract of course. The Cubs signed Heyward to an albatross eight-year, $184 million deal back in 2016, and it’s not set to expire until after the 2023 season. Even worse is that it’s not a tradable contract by any means. Heyward will be 34 by the time his deal expires, meaning his production will go down at his current trajectory.
The odds are stacked against Heyward regaining his speed at an older age — he’s no longer the 24-year-old super-prospect that once ravaged baseball. Instead, Heyward’s defense will deteriorate, and his batting along with it. If the Cubs are lucky, he’ll be replacement-level for the end of his contract.