Of all the days that could be commemorated as among the darkest days in modern St. Louis Cardinals history, December 11, 2015 makes no intuitive sense in terms of where it falls on the calendar, and for future generations of fans, it will make even less sense. And yet, with the exceptions of days on which active St. Louis Cardinals players died, it’s a day which stands above the rest. It was the day that Jason Heyward signed with the Chicago Cubs.

Given the way free agency has trended since that day, Heyward’s decision to sign with the Cubs after having spent the previous season, arguably his best as a Major League player, with their rivals five hours south on Interstate 55 probably makes more sense in 2022 than it did in the moment. Heyward, a young free agent at 26, signed a contract for eight years and $184 million which was reportedly less than what the Cardinals (and others) had offered, but one critical difference was that the contract had an opt-out clause after the 2018 season, when Heyward would be 29.

A player opt-out is an inherently player-friendly contract feature–in practice, it became moot for Heyward as he wisely did not opt out as his performance with the Cubs dropped substantially, but it meant that had Heyward’s potential free agent market increased, he could make even more money down the road. Just this past weekend, Carlos Correa signed a three-year, $105.3 million contract built around opt-outs–he certainly left some money on the table in exchange for the right to pursue more money after a strong 2022 or 2023 season. To this day, the only opt-out the Cardinals have presented to a player was an additional one given to Nolan Arenado in exchange for him waiving his no-trade clause to join the Cardinals from the Colorado Rockies.

On December 11, 2015, there was a ton of vitriol towards Jason Heyward, and while this has largely shrunk to a chorus of moderate booing whenever he steps to the plate at Busch Stadium as his desirability as a St. Louis Cardinals player has precipitously declined, the in-the-moment rage was palpable. But ultimately, a guy who had spent one season in St. Louis and who had never once chosen to play for the Cardinals not being beholden to that organization should never have been surprising, and it’s the kind of expectation that, in the wake of a player lockout where fans sided with the MLBPA in record numbers, may not even exist just six years and three months later.

But this suggests that Heyward’s sudden unpopularity was really about Jason Heyward rather than about what Heyward represented. Despite winning 100 games in the 2015 season, there was a sense of borrowed time to the season that permeated and which kept the team from being nearly as enjoyable as they logically should have been. The Chicago Cubs had emerged from a several-years-long rebuild to win 97 games and eliminate the Cardinals from the postseason with a roster that made the Cardinals look ancient by comparison. Suddenly, the successful local baseball team which had been used as a crutch by generations of St. Louisans as evidence that their hometown was not merely an afterthought to the behemoth that is Chicago looked destined to be second-class. Between Heyward’s departure and the departure of the city’s NFL team less than a month later, it was a rough winter for the self-esteem of the city as determined through sports, as it so often is.

Ultimately, the loss of Heyward did not have any sort of crushing, lingering effect on the Cardinals as a baseball team–his immediate replacement, Stephen Piscotty, had a superior 2016 season to Heyward in right field by the individual metrics, and the man who currently patrols right field for the Cardinals, Dylan Carlson, projects to be substantially better than Heyward in 2022. Carlson’s presence in the Cardinals outfield is directly attributable to the 2015-16 off-season, with Carlson and starting pitcher Dakota Hudson being drafted with compensatory picks acquired thanks to the Cubs signing Heyward and John Lackey, two players who had received qualifying offers from the Cardinals. Of course, Lackey’s qualifying offer was by most accounts as far as the Cardinals went in trying to re-acquire the starting pitcher, hence there was no real animosity towards him despite his (in sharp contrast to Heyward) transparent curmudgeonness.

Two drafts prior to the Carlson-Hudson selections, the Cardinals used a different compensatory pick–one obtained after the loss of Carlos Beltrán–on Jack Flaherty, a pitcher out of Los Angeles’s Harvard-Westlake School. And in ways that are entirely superficial, the spiritual replacement to Jason Heyward in St. Louis was not Stephen Piscotty nor Dexter Fowler nor Dylan Carlson nor any other right fielder–it is Jack Flaherty. And it is about to get as annoying as ever.

Jack Flaherty will play the 2022 season in his second season of salary arbitration eligibility and is scheduled to become a free agent following the 2023 season. None of this should be surprising to anybody with knowledge of how MLB free agency works and the knowledge that Jack Flaherty has been a full-time St. Louis Cardinal since 2018 (though he debuted in 2017), and yet when it comes to Flaherty, it is historically treated as an imminent and unique looming disaster, a treatment rarely applied to fellow pending-in-two-years free agents Harrison Bader, Jordan Hicks, or Miles Mikolas (not that demand for a Mikolas extension is particularly high right now).

Although Jack Flaherty is only 26 years old and on a team loaded with veteran talent, he is the Cardinals’ union representative. And all indications seems to be that Flaherty is going to do the thing that almost all players do anyway and which is very much in the interest of the union at large–he is going to make sure he gets paid. This does not mean that Jack Flaherty would refuse to sign with the Cardinals, nor even that he would refuse to sign an extension prior to reaching free agency–it all comes down to the offer. Could the Cardinals sign Jack Flaherty to a contract which would cost them less than Jack Flaherty would command if he goes out and has two Cy Young-caliber, 2019-esque seasons? Of course they could.

But that is also a calculated gamble that Flaherty, a player who is dealing with (seemingly minor) arm trouble and who will likely miss the beginning of the 2022 season, is going to be this type of player. The most recent Cardinals example along these lines was Carlos Martínez, whose 2017 contract extension was widely viewed in the moment as an absolute bargain, whose diminished production led to the Cardinals declining the two team options at the end of the contract, and by the end led to the Cardinals overpaying for him relative to what he would have commanded in arbitration and free agency.

The Jack Flaherty of 2019 looked like an unstoppable superstar, somebody who would be the rightful heir to Adam Wainwright, Chris Carpenter, and, heck, maybe you’d have to go back to Bob Gibson to find another pitcher worthy of such company. He finished fourth in Cy Young voting thanks to a second half that was as productive as anyone in the sport’s. At the end of the 2019 season, Jack Flaherty was the most important person in my life (note: I didn’t meet my now-wife until a few days after that season, so you snitches aren’t allowed to get me in trouble for this). But in the subsequent two seasons, weird as they were, Flaherty’s production has not been nearly as strong. In nine starts in 2020, Flaherty’s ERA exploded to 4.91, with a FIP of 4.11 suggesting that he did get unlucky but also that he still wasn’t pitching like Prime Jack Flaherty. In 2021, in a season where he was plagued with shoulder trouble, Flaherty did managed a 3.22 ERA in limited duty of 78 1/3 innings, though his 4.22 FIP suggests good fortune on the field.

So what is Jack Flaherty–a future super-ace or just the latest pitcher to succumb to injury troubles? By the ZiPS projection system, Flaherty projects as the sport’s fiftieth best starter in 2022, on the same tier as Jameson Taillon or Chris Bassitt. These are good pitchers, but not pitchers that anyone is mistaking as a Cy Young winner. Flaherty’s projected FIP matches that of Lance McCullers Jr.

In terms of the 2022 Cardinals, this is not an indictment of Jack Flaherty. A Lance McCullers Jr. type may seem a bit underwhelming compared to the Jacob DeGrom or Max Scherzer type that was foreseen in 2019, but this is still a very employable pitcher. But is he a pitcher that must be extended, lest the fabric of the franchise come undone? I would argue that Jack Flaherty is the type of pitcher where you certainly consider an extension if the price is right, but I also can’t blame either party for the lack of agreement. Jack Flaherty might see himself as one of the ten best pitchers in baseball, a pitcher clearly worthy of many tens of millions of dollars per season. The Cardinals might see Jack Flaherty as a talented but highly risky pitcher, somebody who could be one bad night away from being spent. The answer is probably in the middle, but I’m more inclined to buy either extreme from Flaherty than I am from most.

Now, if the Cardinals were to let Jack Flaherty walk as a free agent in two years and replace him with nothing, I’d be pretty ticked off. But if the Cardinals decided that, say, Frankie Montas (as a fellow 2023-24 free agent) is a safer bet for the franchise, this is not an unreasonable stance. Pitchers are a major risk and front offices with finite budgets are sensible to tiptoe around committing a ton of money to them–I can understand never wanting to guarantee money to one unless he is willing to provide a heavy discount in order to do so. Due to Jack Flaherty’s outspoken political views, there is some fairly unfounded speculation that this could be causing shyness from the Cardinals, a team that under the current ownership group let a defending NLCS MVP (Jeff Suppan) who was a couple months removed from participating in a television commercial opposing embryonic stem cell research and did not re-sign Albert Pujols, a guy who was barely a year removed from attending Glenn Beck’s Restoring Honor Rally. Say what you will about Bill DeWitt Jr., a guy whose political donations suggest far more alignment with Suppan or Pujols than with Flaherty–the man wants to maximize the productivity of the team he owns infinitely more than he cares about making a stand on anything.

As for how Flaherty himself feels, his southern California roots mean a constant, pervasive fear that he will be lost to Los Angeles, the eventual landing spot of our wayward Hall of Fame first basemen and professional football teams. In the sense that the Dodgers are a high-spending team, it isn’t completely unreasonable, but the fear that a player will inevitably return to his hometown isn’t exactly grounded in a ton of precedent. Ozzie Smith is also from Los Angeles, and he was never seduced back to his hometown. Adam Wainwright never returned to play for the Atlanta Braves, and he had the bonus factor of having been drafted by his hometown organization. Pre-free agency, sure, but Stan Musial never requested a trade to the Pittsburgh Pirates. Matt Carpenter only signed with his hometown team, the Texas Rangers, after he had exhausted his options with the Cardinals.

None of the top twenty players by ZiPS projected value in 2022 play in their home metro areas, with only Vladimir Guerrero Jr. (born and partially raised in Montreal, though largely raised in the Dominican Republic) being even remotely close, and Montreal and Toronto are still a five-and-a-half hour drive apart from one another. For all of the conjecture about the hometown returns of Matt Olson to the Atlanta Braves and Freddie Freeman to the Los Angeles Dodgers of late, it should be noted that Olson was sent to Atlanta against his will (not that he minded it–he did sign an extension after all, though it is not as though he took some substantial discount to do so) and Freeman only went to Los Angeles after his spot in the Atlanta lineup was officially filled, and by all accounts the Orange County kid grew up rooting for the Angels. That Jack Flaherty is enamored with every Kobe Bryant stan account on Twitter doesn’t mean he’s secretly planning his escape–I would argue that the exact opposite could be gleaned and that the Lakers are the link to his hometown that he actually allowed to continue into his adulthood. By the time Flaherty is a free agent, he will have spent nine-and-a-half years as a Cardinals fan and, assuming he got into following professional baseball at a normal age and that said passion likely dropped off once he became a competitive high school prospect, that will probably be the baseball fandom he has had for the longest time in his life.

Jack Flaherty could re-sign with the Cardinals, or he could find more money elsewhere, but I promise that the process, whether you like the outcome or not, has nothing to do with you, the individual baseball consumer, just as Jason Heyward, while he claimed otherwise in 2015 in order to appease Chicago Cubs fans, did not make decisions for the benefit of anyone but himself or his inner circle family or friends, nor should he. And if the Cardinals do not re-sign him, it is not necessarily a reflection of thriftiness, and it certainly isn’t a reflection of something personal against Flaherty.

Consider what I just explored in borderline excruciating detail with Jack Flaherty, and instead apply it to Harrison Bader. Why is there not such concern that Harrison Bader, whose favorite team growing up is a matter of public record (the New York Yankees), won’t re-sign? Like Flaherty, Bader has flashed brilliance and would command a large salary if he maintains his quality of play for the next two seasons, and like Flaherty, there is risk–in extending a center fielder whose game is largely predicated on speed into his thirties, just as “signing a pitcher of any variety, much less one with documented and recent shoulder trouble” is a risk. In neither case is it worth worrying about too much–these are guys whose top Baseball Reference comps are Doc Medich and Vince DiMaggio, not Doc Halladay nor Joe (or even Dom) DiMaggio, good players but not guys who went down in history as so essential that it would have been a crime to not keep them around forever.

I’ve extracted a ton of joy from watching Jack Flaherty pitch. I absolutely do not understand the animosity around him that has sprung up because he…got hurt (I can’t fathom a player with less incentive to get hurt than a guy who, if he stays healthy for the next two years, is going to be worth nine figures)? The Cardinals should/will/probably already have made some sort of effort to retain Jack Flaherty, but it’s perfectly reasonable from both sides that what they are willing to offer does not align with what he is willing to accept. And that’s fine.