’Twas the winter of 2015-16. Jason Heyward wasn’t the best-available player in a well-stocked free agent class. But he was a high-quality performer and still tantalizingly young (26). While hardly a traditional corner outfield star due to his middling power, Heyward was well-established as a quality hitter and superlative defender and baserunner.

The debate raged long before the offseason arrived: how much can you really pay for a player like this? All agreed he was good. But the traditionalists howled at the notion of a right fielder who hadn’t even hit forty home runs over the prior three seasons landing a premium contract. The analytically minded countered that, well, runs are runs regardless of how they’re added or prevented. Heyward was a 6.9 rWAR / 5.6 fWAR performer in 2015. With exceptional glovework and a steady OBP, Heyward seemed to be a high-floor player who might have some ceiling as well.

[RELATED: Jason Heyward & Chris Davis Have Two Of The Worst Free Agent Contracts … In Different Ways]

We predicted that Heyward would earn $200MM over a full decade — second-most in a rather well-stocked free agent class. That didn’t quite happen, but the real deal was actually more favorable to Heyward than the one we had guessed. He landed $184MM over an eight-year term and also got two opt-out opportunities (which was worth something at the time the deal was struck, even if they weren’t exercised). The deal delivered a nice $23MM AAV over quite a lengthy term.

Now that we’re all reacquainted with the contract as it turned out … let’s try to remind ourselves of the state of play in the market when it was struck. At the time of the pact, there were hints that the Cubs may not have been the high bidder. The Nationals supposedly had the top offer on the table, though we may presume it’d have been deferred. The incumbent Cardinals were also known to be in pursuit. And the Angels and Giants were still involved in rumors right up until the end.

So … what would things have looked like if Heyward had landed elsewhere?

Nationals

Whoa … would the Nats have hoisted the commisioner’s trophy last fall had they signed Heyward? That’s obviously not something that can be assessed fairly given the innumerable butterfly effects potentially at play. But the counter-factual does actually present a pretty similar situation to what actually happened in 2019. In right field, the Nationals got solid but hardly otherworldly work out of Adam Eaton — another left-handed hitter whose skillset is rather similar to that of Heyward.

More interesting to consider is the fact that the Nats probably wouldn’t ever have dealt for Eaton had they already acquired Heyward. Eaton landed in D.C. after the team missed on its effort to acquire Chris Sale for the White Sox. The swap cost the Nationals pitchers Lucas Giolito (reimagine 2019 with him on the staff), Reynaldo Lopez, and Dane Dunning. Of course, Eaton has been much more affordable than Heyward this whole time. Who knows if the Nats would’ve inked Patrick Corbin last winter had Heyward been on the books.

Ultimately, the Washington organization has deep enough pockets that it would’ve been just fine with an underperforming $23MM salary on the books — not unlike the Cubs. At the same time, also not unlike the Cubs, the Nats have been focused on getting and staying just under the luxury tax line, so this deal would’ve been a constant nuisance that would’ve interfered with any number of lower-cost veteran signings and acquisitions over the past several seasons.

Cardinals

Much like the Nats, the Cards eventually made a big deal for a somewhat similar player. One winter after missing on Heyward (despite reportedly offering as much or more as the arch-rival Cubbies), the Redbirds reversed the talent flow by inking former Chicago center fielder Dexter Fowler. The switch-hitting Fowler wasn’t nearly as expensive as Heyward, but his own five-year, $82.5MM deal has worked out about as poorly. The Fowler contract probably wouldn’t have been signed had Heyward been around, but this is probably to the Cardinals’ benefit since the Heyward deal features a bigger and longer hit. Perhaps the Cubs would’ve ended up retaining Fowler had they missed on Heyward. You could argue over the details, but it’s probably not far from a wash.

Of course, the Cards went without either of those players in that 2016 campaign … which helped open the door to the memorable shooting star of Jeremy Hazelbaker. It’s tough to say whether there were significant long-term effects on the way the Cards’ outfield picture developed. Going without Heyward in 2016 opened more playing time for outfielders Randal Grichuk, Stephen Piscotty and, to a lesser extent, a pre-breakout Tommy Pham. Perhaps one or more would’ve been shipped out of town earlier had Heyward been retained. Maybe Pham’s breakout would’ve occurred elsewhere, thus eliminating his successive trades (to the Rays and then to the Padres), though it’s impossible to say that with any degree of confidence.

Angels

We don’t know whether the Halos were really strong pursuers of Heyward, but it’s worth considering what might’ve been. The club ended up foregoing any big free agent splashes that winter. (It had already acquired Andrelton Simmons.) Adding Heyward surely wouldn’t have forestalled the string of four-straight losing seasons, given the way he has played. But it might’ve prevented the Angels from eventually trading for and then extending Justin Upton. And it certainly could’ve gummed up this winter’s signing of Anthony Rendon.

Giants

Likewise, it’s not entirely clear that the Giants were heavily involved in bidding up Heyward’s price, but the team clearly had some real interest. The San Francisco org splashed a lot of regrettable cash that winter regardless. It had already inked Jeff Samardzija and ended up signing Johnny Cueto after Heyward landed with the Cubs. The Giants did find a rather direct alternative to Heyward, inking Denard Span to a three-year, $31MM pact. That didn’t quite go as hoped but was hardly a significant disaster. Suffice to say that having Heyward on the books would’ve further complicated an already difficult stretch for the organization.

Cubs

Ah, yes. The Cubs. Lauded at the time by some for landing Heyward for less than others would’ve paid — really, the deal was probably right at the market rate, give or take — the Cubbies have obviously not benefited from the signing.

Remember how we started this post? The debate over paying out a non-slugging right fielder. Consider these contemporaneous comments. On the one hand …

On the other …

To some degree, neither turned out to be right. And the lack of power was largely beside the point. Heyward did top twenty long balls in 2019, but he was still an average-or-worse hitter for the fourth-straight year. It was certainly his best offensive season for the Cubs … but also the team’s own worst effort in this four-year span. No, the Cubbies haven’t exactly dominated the National League over the span of this deal, but they did capture that elusive crown in 2016.

So does the World Series justify it? Eh … this isn’t as clean an analysis as the Gleyber Torres-for-Aroldis Chapman “you do what it takes!” situation. Heyward was terrible in 2016 and even worse in the postseason, when he contributed just five hits and a walk over fifty plate appearances.

There’s no two ways about it: the deal hasn’t worked out at all as hoped. Heyward has by all accounts worked hard and been a total class act, as ever. And he has trended back up with the bat, which is somewhat promising with regard to the final three seasons of the deal. But the net return to the Cubs — 7.1 rWAR and 6.0 fWAR — has not remotely justified the outlay.

Anybody that has watched the Chicago organization operate these past two winters can see the effects of this contractual miss. The Cubs have decided not to move past the luxury tax line, so every dollar going to Heyward has been another buck that couldn’t be allocated elsewhere. Of course, the Heyward whiff isn’t the only one that has stung in recent years, as MLBTR’s Tim Dierkes recently examined. And it’s worth emphasizing the he’s still just 30 years of age and still capable of contributing. It’s not outside the realm of possibility that he could even morph back into a quality regular. All things considered, this contract certainly didn’t single-handedly obstruct the Cubs’ dynasty-that-wasn’t … but it certainly played a leading role.

Photos courtesy of USA Today Sports Images.