19. Chicago Cubs
The richest contract in Cubs franchise history went to a .245 hitter with a lifetime 86 OPS+ during his time with the team. But brother, could he deliver a speech.
In Chicago, it was Jason Heyward’s oratory — specifically the speech he delivered in the weight room at Cleveland’s Progressive Field while waiting out a rain delay prior to the 10th inning of Game 7 of the 2016 World Series — that made him famous.
His teammates credited Heyward with rallying the club after a Rajai Davis home run erased a Cub lead and appeared to put Cleveland on track to win the Series.
A player can contribute in many ways. Heyward may not have justified his eight-year, $184 million contract with his bat. But if his William Jennings Bryan weight room imitation did indeed set the Cubs on course for their first World Series win in 108 seasons, all is forgiven in Chicago.
For AAV, Heyward’s contract was surpassed by the six-year, $155 million contract the team gave his teammate, pitcher Jon Lester. That works out to $25.8 million per year. Lester didn’t hit either, famously couldn’t throw to a base and he didn’t talk much, but the guy could sure pitch.
He went 77-44 for the Cubs, including 19 victories in that 2016 World Series season and 18 more in 2018.
As for Heyward, the Cubs released him following the 2022 season, opting to eat the final $22 million. He has since signed a minor league deal with the Dodgers.