T-8. Jason Heyward, Chicago Cubs, 2016-2018, +5.2
This one’s totally arguable. The Cubs, after all, won the World Series the year they signed Heyward, and by all accounts he played a central role in that outcome…if only via an especially inspiring pep talk during a seventh game rain delay that all present agreed rallied his team.
On the field, Heyward’s contributions since signing that eight-year, $184 million contract have been less profound. In none of his first three seasons with the Cubs has his WAR exceeded +2.3, making him a competent regular but hardly a centerpiece.
His batting averages have improved steadily in Chicago, but that more reflects the low bar set by his initial .230 season. That’s 30 percentage points below his career average; he’s since produced average numbers.
So the real question about the Heyward contract is whether a career .265 hitter with average power and on base numbers was ever worth $184 million in the first place. By most measures, his best season was his first, when he hit .277 with 18 home runs, figures that generated a 131 OPS+.
Otherwise, the Cubs are getting almost exactly what they should have expected; they’re simply paying a premium price for it. On the other hand, they did win that World Series…and Heyward did play a key role. So even if he was paid $188 million merely for his oratorical skills, Cubs fans may see that as money well spent.