Our recurring list of the twenty-five greatest Cardinals of the last twenty-five years will run daily leading up to Opening Day 2021. In case you missed it, here are the prior entries.

Honorable Mentions

25. Todd Stottlemyre

24. David Freese

23. Andy Benes

22. Lance Lynn

21. Paul DeJong

20. Tommy Pham

19. Darryl Kile

18. Ryan Ludwick

17. Kolten Wong

16. Carlos Martínez

15. Woody Williams

14. J.D. Drew

13. Brian Jordan

12. Edgar Renteria

11. Ray Lankford

10. Matt Morris

St. Louis, somewhat out of a desire for self-mythology but also somewhat accurately, loves to perceive itself as a hidden gem, a city that is quietly great and may not have the flash of, say, Chicago, but has everything you could love in a city (or a town, depending on what specific angle of charm the St. Louisan is trying to evoke in the moment). In many ways, St. Louis sees itself as Matt Holliday.

Matt Holliday never led St. Louis Cardinals position players in Wins Above Replacement for a single season, but he finished in second place three different times, each time trailing a different player. And for good measure, he finished third on two additional occasions. At his peak as a Cardinal, a clumsy defensive miscue became his defining moment. When Matt Holliday won his lone career World Series title, he was hurt for Game 7 and had a truly terrible Game 6, categorized by a lousy defensive error and inexplicably being picked off third base by barely-even-a-catcher Mike Napoli. And when Matt Holliday made his final appearances in a St. Louis Cardinals uniform, concluding what was easily the worst season of his Cardinals career, he received a series of standing ovations from the Busch Stadium crowd befitting a lifelong Cardinal who was to be a first-ballot Hall of Famer.

Holliday wasn’t a lifelong Cardinal, playing just over half of his career games with St. Louis, and he won’t be a first-ballot Hall of Famer–he likely won’t even reach the 5% of votes needed to remain on the Hall of Fame ballot for a second season. In terms of historical significance with the Cardinals, he isn’t near the top of the franchise leaders in any category except one–Matt Holliday signed the largest free agent contract in franchise history, and has held the record for over eleven years. There are a ton of caveats attached here–Holliday had previously been a Cardinal prior to signing as a free agent, his annual salary has been eclipsed (just not the grand total over the course of the contract), and the Cardinals have both traded for a larger contract (Nolan Arenado) and signed a non-free agent to a larger contract (Paul Goldschmidt). And not the least of the caveats is that, as far as free agents go, the Holliday contract worked out pretty well for the Cardinals–he was very productive for the first few years, and while its value tailed off towards the back end of the contract, that is common. FanGraphs estimates that over his seven-year contract, signed before the 2010 season for $120 million, Holliday would be worth $167.7 million on the open market.

The transaction which initially brought Matt Holliday to St. Louis, however, was a 2009 trade–Holliday from the Oakland Athletics in exchange for three prospects: Clayton Mortensen (the only of the three to have made his MLB debut with the Cardinals–he had pitched three total innings), Shane Peterson, and most notably 2008 first-round draft pick Brett Wallace. And while the trade seems lopsided on the surface, the Cardinals were trading some fairly notable prospects for two months of Matt Holliday, a pending free agent (and one whose eventual re-signing was neither inevitable nor particularly viewed as a hometown discount when it came to fruition). But none of the three prospects turned into significant big leaguers–Mortensen and Wallace were sub-Replacement Level for their careers and while Peterson did have a decent season in 2015 with the Milwaukee Brewers, the Cardinals were never going to hold on to him that long without making some sort of MLB impact.

And Holliday, despite only two months with which to work, was a superstar for the Cardinals. Holliday had long been the obvious best hitter on the Colorado Rockies, but instead, he was slotting comfortably behind Albert Pujols in the Cardinals’ lineup. In 270 regular season plate appearances, Holliday hit 13 home runs and crafted a 1.023 OPS. He even received some down-ballot MVP votes despite not making his debut in the National League until July 24. Yet despite his tremendous success down the stretch for the Cardinals, and despite a go-ahead home run off Clayton Kershaw in Game 2 of the 2009 NLDS against the Los Angeles Dodgers, it was a moment later in the game that defined Holliday’s whole campaign for many. On a sharp line drive off the bat of James Loney, Holliday whiffed on making what would have been a game-ending catch and instead, the ball hit Holliday in the groin. A series of subsequent events made this error crucial, as the Dodgers completed a comeback to win the game and eventually sweep the series. The miscue was a play Holliday should have made, but it also wasn’t quite a lazy pop fly, and the legacy of the play turned Holliday, an unspectacular though largely functional left fielder, into a bumbling mess of a defensive liability in the eyes of some.

Over the next five seasons, Holliday was astonishingly consistent at the plate. Injuries limited him to “only” 516 plate appearances in 2011, but aside from that, Holliday’s plate appearances from 2010 through 2014 ranged from 602 to 688. Each year, Holliday hit between 20 and 28 home runs. His wRC+ landed between 132 and 154, with the three median seasons in the 140s. His walk rate sat above 10%; his strikeout rate was a tad higher, but always below 20%. His defensive numbers declined in a predictable fashion, gradually falling from pretty good to average to “well, he’s not great out there, but he still hits like Matt Holliday”, but at the plate, while other players took turns as the team’s biggest star, Holliday remained a rock.

In 2015, Holliday dealt with lingering injuries for the first time in his career, with separate Disabled List stints caused by quadriceps strains. When healthy, he was still a good hitter, but his style of play had changed–in 277 plate appearances, he did draw a walk in a career-high 14.1% of his plate appearances (this was a big part of why he managed a 45-game on-base streak to start the season), but he hit just four home runs. He struggled in the postseason, with just two base hits–both singles–and a walk in seventeen plate appearances against the Chicago Cubs in the NLDS. Due to a glut of young outfielders and questions about incumbent first baseman Matt Adams, the Cardinals announced entering the 2016 season that Holliday would begin seeing some time at first base for the first time in his professional baseball career.

Despite the hype, Holliday still played primarily in left field in the final guaranteed year of his Cardinals contract. His walk rate dipped, and his batting average on balls in play fell, but Holliday did see a resurgence in his power, with 19 home runs through August 11. But on that date, a pitch from the Chicago Cubs’ Mike Montgomery hit Holliday in the thumb, breaking it and requiring surgery. The timetable of his return left it a very open question as to whether or not Matt Holliday would ever take another at-bat in a Cardinals uniform. On September 30, a pair of Holliday announcements managed to overshadow the Cardinals’ quest for a Wild Card berth–one, that Holliday was going to be reactivated for the coming series against the Pittsburgh Pirates but that he would likely be limited to pinch-hitting duty at best, and two, that the Cardinals did not plan to pick up Holliday’s $16 million option for 2017.

By that night, the Cardinals had prepared stadium graphics packages thanking Holliday, a well-intentioned but strange gesture which effectively announced that under no circumstances would Holliday be returning to St. Louis. At this point, Holliday was seen as there to say final goodbyes and maybe cameo in the event of a decisive lead, and the team’s 5-0 lead in the seventh inning allowed such a moment–a pinch-hitting appearance with no runners on. And while Holliday looked to be laboring on his first swing, a second-pitch foul ball, he drove the third pitch the opposite way into the Cardinals’ bullpen. For as much grief as St. Louis gets for wanting an endless string of curtain calls, this was a reasonable time for one.

As poignant and as exhilerating as the home run was, it ultimately would have been an off-brand way to culminate a Cardinals career defined by steady competence rather than emotion. And the next day, Holliday was able to take his final Cardinals plate appearance in a much more Holliday-esque manner: with a one-out RBI single which sent Randal Grichuk to third base, from which he would score on a fly ball one pitch later. It’s a less anthologized moment than his home run, but it was inarguably more consequential, as it pushed the Cardinals to a very necessary win on the final weekend of the season, and it captured the essence of Matt Holliday far more closely. The next day, with a Cardinals victory assured in the ninth inning, Matt Holliday took his familiar spot in left field for the first time all weekend. One pitch later, he was removed from the game. And for the third consecutive day, he received a standing ovation.

Matt Holliday never had a positive defining postseason moment in St. Louis. He never chased a major record. And on August 11, 2016, it seemed like Holliday, who would later sign as a designated hitter with the New York Yankees, would never get to have one. It seemed that Holliday would go down as a very good Cardinals player, but a player far better defined by the raw numbers of his career than any kind of overarching, emotional narrative. But on the final weekend of the 2016 season, the man who had embodied the Cardinals and had embodied St. Louis got his moment. And the crowd went wild.

9 thoughts on “The twenty-five greatest Cardinals of the last twenty-five years: #9–Matt Holliday

  1. Two things I remember from when they Cardinals got Holliday to sign that free agent contract:

    One, the perception the Cardinals bid against themselves and way overpaid. Which, as you noted, they actually got surplus value. From a team perspective the Holliday deal has to be one of the best long free agent contracts, right? Maybe him, Adrian Beltre, maybe Scherzer?

    Two: that there was some debate over whether Holliday or Jason Bay was the better free agent outfielder that off-season (presumably because Bay was coming off a 5-win season in Boston). Bay signed with the Mets for substantially less than Holliday got, but promptly either got hurt or just bad. Worth 2.3 bWAR total over the remaining four years of his career.


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