Last night, Pete Alonso of the New York Mets defeated Trey Mancini of the Baltimore Orioles in the final round of the 2021 Home Run Derby. Highlights of the night included a double-overtime first-round matchup between eventual round victor Juan Soto of the Washington Nationals and Shohei Ohtani, the Los Angeles Angels pitcher/designated hitter/overall sensation who will also start tonight’s All-Star Game. It is unlikely that I remember in a week who won the Home Run Derby. Every year, it is pure instant gratification–delightful and exhilerating in the moment but without any real dramatic consequences. And it’s super fun because of it.

What’s somewhat unusual about the Home Run Derby is that its primary draw–seeing how far the sport’s best home run hitters can crush what are effectively batting practice pitches–isn’t really what makes in-game home runs fun. Context does. Most of the most celebrated home runs in baseball history were not particularly long home runs, and if they were, that’s probably beside the point. The real draw is situationally important moments, ones which cement a big victory and/or break the hearts of the opposing fans. The greatest home runs in St. Louis Cardinals history, for instance, aren’t necessarily the longest. Sometimes, they’re even among the shortest.

In honor of last night’s eight Home Run Derby participants, here is an entirely subjective look at the eight greatest home runs in St. Louis Cardinals history. I am probably missing something obvious, to my great shame.

#8–Jack Clark

Overshadowed by a different 1985 NLCS home run, Jack Clark’s blast in the ninth inning of its sixth and final game should not go unnoticed. From a sheer game Win Probability standpoint, it was a massive coup–due to there being two outs and with the Cardinals trailing by a run, their Win Probability when Clark stepped to the plate against Tom Niedenfuer was only around 19%. But following Clark’s first-pitch swing, which sent the baseball well over the Dodger Stadium left field fence, the team had a comfortable two-run lead and a 93% chance of victory, which came to fruition in the next half-inning, sending the Cardinals to the World Series for the second time in four years.

#7–Jim Edmonds

Although Clark’s home run was more significant in the context of the baseball game being played–after all, his team was trailing–the drama of a walk-off is impossibly enticing. And in an NLCS Game 6, with your team on the ropes against a Houston Astros roster far hotter than their 92-70 record would suggest, nothing ever felt certain. And the finality that came with a beautiful swing to end a game at just past 7 p.m. is an undeniable aesthetic delight to revisit for any Cardinals fan.

#6–Whitey Kurowski

Kurowski’s winning home run in Game 5 of the 1942 World Series is almost certainly the least famous of the franchise’s great dingers (why no, I don’t have video to share), but on the off chance that somebody who remembers the 1942 World Series is reading this, I am certain I do not have to spend much time justifying this pick. The 24 year-old third baseman came to the plate at Yankee Stadium against the legendary Red Ruffing and socked a two-run blast down the left field line to break a 2-2 tie and give the Cardinals a 4-2 lead, which the team would retain en route to their fourth World Series championship a half-inning later.

#5–Mark McGwire

It’s the least significant home run in terms of winning baseball games on this list by a mile. It is certainly the least impressive to watch. It is the home run on the list which has aged the worst. But Jack Buck, as good of an authority as any on the matter, proclaimed Mark McGwire’s 62nd home run of the 1998 season the greatest home run in baseball history when it happened. It’s impossible to articulate just how massive of a story the 1998 chase of Roger Maris’s single-season home run record was. And even though McGwire’s single-season record would fall just three seasons later, the Barry Bonds chase never captured the attention of the baseball-loving public with the same intensity as what unfolded in the Summer of 1998.

#4–Albert Pujols

Maybe it’s because I watched this one live and the Jack Clark one happened before I was born that my preferred top of the ninth, go-ahead home run in the NLCS is Albert Pujols’s towering Game 5 home run in the 2005 NLCS. Maybe it’s because I have a preference for the dramatic moment that comes when the team is facing intense adversity–after all, if Jack Clark had struck out, there would have been a Game 7 in that NLCS, but if Pujols had been retired, the season was over. Maybe it’s the before-and-after Win Probabilities–7% changes in an instant to 81%–that I find impossibly appetizing when looking back. Or maybe it’s just because I have never seen an important home run go so impossibly far.

#3–Ozzie Smith

The element of the unexpected is hard to overlook. It’s one thing for Albert Pujols to hit a heroic postseason home run, but Ozzie Smith? He had been developing into a competent offensive player, sure, but he certainly wasn’t a slugger, and he definitely wasn’t a power hitter against right-handed pitching, as the game’s television broadcast noted just before the home run that Ozzie Smith had never hit a home run against a righty. But then, the seemingly impossible happened, and the defensive specialist took Tom Niedenfuer (who, to his eternal credit, was still willing to eventually sign with the Cardinals in 1990) deep to walk off Game 5 of the NLCS. It’s strange that the finest moment of both Ozzie Smith and the 1985 Cardinals was a home run; it is also arguably the finest broadcasting call in franchise history.

#2–Yadier Molina

Speaking of unexpected moments, how does a home run to send the Cardinals to the World Series hit by one of the worst hitters in Major League Baseball sound? Although Molina would eventually become a formidable offensive threat and was even downright feared for a few years, the 2006 version that hit a two-run home run in the top of the ninth at Shea Stadium in Game 7 of the NLCS against the New York Mets was not that guy. A home run wasn’t even a consideration, and with the bottom third of the order due up, extra innings seemed like the best case scenario for the Cardinals. Along with Ozzie Smith, the great irony is that the two greatest defensive players in franchise history had their greatest moments as postseason home run hitters.

#1–David Freese

It may not even be the greatest David Freese moment in this game (I’m more of a ninth inning triple man, myself), but it’s hard to argue against the only walk-off home run for the Cardinals in franchise history as the greatest home run in the history of the team. It checks nearly every box you could hope for. A home town hero? Somebody who had developed Cardinals lore, like, an hour earlier? A home run that, thanks to the events of the next night, would not be an interesting sidenote to a Texas Rangers World Series victory? It happened a decade ago and I still can’t stop watching it.