No. 1: Jason Heyward, $38.5M remaining
This is a forward-looking exercise, so if you want to argue the remaining six-plus guaranteed seasons of Yelich’s contract are a bigger risk than Heyward’s final couple of years, that’s understandable. But Yelich has been between average and great for the Brewers, with indications he can get back to being a very good player. The odds of Heyward doing so appear much longer.
The Cubs won the bidding for Heyward’s services over his previous team, the Cardinals, after he completed a 2015 campaign during which he earned his third Gold Glove and receive MVP votes for the second time. Unfortunately, winning the battle seems to have resulted in losing the war.
White Heyward won two more Gold Gloves in his first two seasons on Chicago’s North Side, his bat was decidedly subpar. Never a power hitter, he combined for just 18 homers combined those first two years and had slugging percentages below .400 both seasons. The bat got better the next three years, but the glove was no longer award-winning.
And since 2021 started, Heyward has been reduced to a part-time player. He appeared in just 104 games last season, batting .214/.280/.347 with eight home runs, and this year has been similarly poor, with a .208/.288/.264 line and only three extra-base hits (no homers) in 80 trips to the plate.
Is Heyward done? Quite possibly. Is this view of his future salary obligations tainted somewhat by his past underwhelming performance? Could be. But considering where the Cubs are today, how Heyward is playing, and how much he’s being paid to do so, this is arguably the worst contract among any players in the entire National League Central.