Seven years on, it’s easy to forget that the Chicago Cubs’ decision to sign Jason Heyward to an 8-year, $184 million deal in 2016 was met with media fanfare.
Jesse Rogers of ESPN described the outfielder as “an all-around player who brings a skill set the Cubs were lacking” while his colleague David Schoenfield labelled the move “the capper to the rebuilding job by team president Theo Epstein and general manager Jed Hoyer”.
The signing was also seen as something of a coup, as the Cubs fended off interest from more seasoned opponents like the Nationals and Cardinals amongst others, eventually signing Heyward for quite a bit less than the circa $200 million deal rival teams were reportedly willing to give him.
That was back in December 2015, before the Cubs won the World Series; before Heyward’s numbers declined; and before some sections of the fanbase started calling for him to be cut from the team.
Those were heady days for a franchise still basking in the glow of a season that saw them go all the way to the National League Championship Series. But while it acknowledged that the Cubs “got its man,” Rogers’ also article featured a glimpse of the future.
“The downside to the deal comes if Heyward isn’t very good and the Cubs are stuck with him for eight years,” he wrote. “The deal is back-loaded, according to a source familiar with it, so the Cubs should reap the benefits of it early, but if he’s not very good later in the contract he’ll be eating up a bigger part of their payroll.”
That is, pretty much word for word what happened, as Heyward’s contract quickly became a source of angst for a fanbase frustrated by a team that fell a long way short of the dynasty many believed they were destined to become. But as Schoenfield observed at the time, “Heyward has been maligned for his lack of power, but I think he has grown comfortable in understanding what kind of hitter he is: get on base, pop a few home runs, run the bases.
“He’s entering his age-26 season,” he continued, “so the Cubs get his prime years. There’s a small chance he improves at the plate, but I wouldn’t bet on that. Still, he projects as valuable a player over the life of the contract due to his defense and on-base ability.”
Heyward didn’t hit a lot of home runs as a Cub or improve as a hitter, but he did win two of his five career Gold Gloves during his time with the team, while his greatest contribution of all famously came in the form a speech delivered during the 17-minute rain delay that turned Game 7 of the 2016 World Series on its head.
Most fans didn’t really care about the intangibles though. They didn’t care about the breath-taking catches, the bullet arm, the leadership, the mentorship or the countless hours Heyward spent contributing to the community. They wanted to see him hit, because that’s how the highest-paid position player on any roster repays the investment in him, right?
Not in the eyes of then GM Jed Hoyer, who, as Jon Greenberg wrote in his 2019 ‘If These Walls Could Talk’ book on the Cubs, said shortly after Heyward’s signing: “I think when you look at the way you evaluate his total contribution to the game, I think he’s an exceptional player. People have talked a lot about the standard way people get compensated and how that’s changing. I do think more and teams, and baseball fans, are looking at the totality of the player’s contribution to the game as opposed to simply the offensive contribution.”
While he wasn’t necessarily right about this, Dave Cameron of FanGraphs adopted a similar view in an article that considered what the Cubs would need to get out of their new acquisition in order to “break even on the total guaranteed money in this deal”.
In the piece, which was written in December 2015 and assumed that the deal would be worth $181.9 million over 8 years – slightly less than it actually was, Cameron claimed that Heyward “would have to only put up about +20 WAR” during his tenure for the Cubs to ‘break even’.
To that point in his career, he had already been worth +28 WAR in six years in the majors while notching a solid 5.6 WAR in 2015 alone with the Cardinals. Being realistic, Cameron front loaded the model, assuming Heyward would accumulate 13.1 of his total WAR before hitting his age-30 season in 2020 and using the second of the two opt-outs that were written into the deal to become a free agent again.

His calculations couldn’t have been more wrong though, as Heyward was actually worth just 7.1 WAR in that time and 8.4 total WAR during his seven seasons with the Cubs, according to Fangraphs. Using the site’s ‘dollars’ metric (WAR converted to a dollar scale based on what a player would make in free agency), Heyward’s time with the Cubs has been worth roughly $67.6 million – just over a third of what he actually ended up costing them.
Incredibly, 2016 was one of his worst years in this regard too, as Heyward was worth 0.9 WAR (he’s only logged a lower WAR in the past two seasons) – 389th best among all eligible players, as he hit .230 / .306 / .325 with a .631 OPS and considerably worse in the postseason.
Things did improve slightly over the next couple of years, as he managed 2.7 WAR in 2018 and 2.2 WAR in 2019 before his numbers dropped off again.
Sadly, the Cubs followed suit, sunk by an aging rotation, regrettable free agent signings like Brandon Morrow and Tyler Chatwood, a farm system depleted by ill-advised trades and a young core that got increasingly worse as it approached its collective prime. And yet they achieved what they set out to, far earlier than expected, and Heyward played a huge part in that; one that can’t be measured by a FanGraphs metric and one that he characteristically downplayed in the aftermath.
Wrigley Field remembered that when saying goodbye to Heyward on Saturday, at once grateful for what he’s done for the team and the city while relieved that one of the worst contracts in Chicago sports history is almost at an end.
Photo by Quinn Harris / Getty Images
Sean is Bat Flips & Nerds’ Chicago Cubs correspondent for the 2022 season. You can follow him on Twitter @SW_Guest