The St. Louis Cardinals and San Diego Padres have engaged in several trades over the years, and despite the time they acquired prospect-turned-setup man-turned-eventually a Cardinal again Luke Gregerson in exchange for, as it turns out, on borrowed time shortstop Khalil Greene, the Padres have generally been on the short end of the stick when it comes to these trades.

Below is a ranking of four great Cardinals/Padres trades, and when I say great, I mean they were great for the Cardinals, which is an inherently good thing because the Cardinals represent everything in the world which is good and pure. Did I miss any great trades? It’s certainly possible. But these are very good ones and I feel that ranking these trades is still a fair thing to do.

4. 2001–San Diego Padres trade Woody Williams to the St. Louis Cardinals for Ray Lankford and cash

What the Padres were thinking: “Wait, so you’re telling us we can give you Woody Williams, the very definition of Just A Guy as a starting pitcher, who is going to turn 35 later this month, and you’re going to give us Ray Lankford, the best player for the St. Louis Cardinals during the 1990s? Oh, and you’re going to give us cash while you’re at it? I mean, sure I guess.”

What the Padres were eventually thinking: “Okay, so we didn’t really need Ray Lankford to be great in 2001, but he hit well after coming over for the last two months of the season. And then 2002 happened and, well, it turns out an 87 wRC+ and poor left field defense make one among the least valuable players in baseball. Hey, at least he got to hang out with Ron Gant again! But whatever, whatever, it’s Woody Williams, who cares what Woody Williams d…his ERA was what? 2.53? He was a 3 WAR pitcher despite only pitching 103 1/3 innings? How did he…ah, right, he’s a soft contact guy and the Cardinals had four guys win Gold Gloves that year. But I’m sure you missed having Lankford available to play left field…oh, right, you just put Albert Pujols there. That…that works.”

3. 2015–San Diego Padres trade Jedd Gyorko and cash to the St. Louis Cardinals for Jon Jay

What the Padres were thinking: “Jon Jay? I mean, I know he’s generally been pretty good but maaaaan was he a bad hitter in 2015. A 58 wRC+? Y’all ran Pete Kozma out of his spot on the team for a 49 wRC+ while he played Gold Glove-caliber shortstop a couple years ago; Jay’s just kind of a decent outfielder. Can’t say we’re dying to give him $6.2 million next seas…oh, Gyorko? The guy who has been below Replacement Level over the last two seasons who we owe $33 million in guaranteed money going forward? Because you don’t want to pay Jon Jay how much again? I mean, yeah, I guess we could swing that. You know what? Here’s $10 million while we’re at it. Yeah, yeah, have fun paying a utility infielder $13 million in 2019.”

What the Padres were eventually thinking: “Hey, Jon Jay rebounded nicely! Can’t complain about a 101 wRC+; he may not be a superstar but for the return in a salary dump, can’t complain. Now let’s check in on Jedd Gyorko, who…led the 2016 Cardinals in home runs. Okay…and was comparably good at the plate in 2017, and is off to a torrid start in 2018. But defensively, I bet he…oh, he demonstrated strong defense at third base and spent time at all of the other infield positions in St. Louis. I know we aren’t very good but we could’ve gotten some actual prospects for Gyorko had we known he’d turn into this. I mean, we got Fernando Tatis Jr. for James Shields. We could’ve gotten…better than Jon Jay.”

2. 2007–San Diego Padres trade David Freese to the St. Louis Cardinals for Jim Edmonds

What the Padres were thinking: “Oooh look at that, Cardinals. You may be the NL’s team of the 2000s, and you may have beat us in two consecutive postseasons in 2005 and 2006, but you lost more games than you won in 2007, and we won 89 games and might’ve made the playoffs if not for Matt Holliday inexplicably being called safe despite not touching home plate. But anyway, we have the power now, and you’re looking to rebuild. You don’t need Jim Edmonds anyway; you’re not going anywhere. Anyway, we’ve got this kid in the minors from your neck of the woods, Freese, hit well last year in high-A but, you know, gotta level with you, he was 24. Not exactly a high-end prospect. But take it or leave it. We have the power here. We’re the San Diego Padres. You’re the St. Louis Cardinals. We own baseball.”

What the Padres were eventually thinking: “Hm, so perhaps a 37 year-old center fielder wasn’t the safest bet. A 40 wRC+ in 103 plate appearances, poor defense, we had to cut him. Not great, but whatever, we only gave up a low-level minor leaguer to get him. It was a low-risk move. Hey, did David Freese ever make the big leagues?”

  1. 1981–San Diego Padres trade Ozzie Smith, Steve Mura, and a player to be named later to the St. Louis Cardinals for Garry Templeton, Sixto Lezcano, and a player to be named later

What the Padres were thinking: “Okay, this one seems pretty simple to us. Garry Templeton’s a really good two-way shortstop. Kid can hit, kid can field, he seemed miserable in St. Louis, and he’s going to have just turned 26 by Opening Day. And Ozzie Smith–great fielder. Immaculate fielder. Probably the best defensive shortstop since Mark Belanger. But he can’t hit. He’s never hit. He’s 27 years old and his offensive peak was an 84 wRC+, a stat which definitely exists in 1981, as a rookie. He’s played four full seasons and has one home run. Let Whitey Herzog be in love with defense. Give us Templeton.”

What the Padres were eventually thinking: “Hey, we got our shortstop for a decade! Sure, Garry wasn’t a superstar, but he was an All-Star in 1985 after winning a Silver Slugger in 1984. Can’t complain. Now let’s see what Ozzie did…looks like he also got a Silver Slugger award! That’s nice, we really weren’t trying to swindle you, and we like Ozzie personally. A mutually beneficial trade it seems…wait, what was that? How many All-Star Games was that? Four? Okay, well, sure, that beats Templeton’s…oh, fourteen? And how many Gold Gloves? Eleven? And he’s *squints at numbers* the greatest defensive player in the history of baseball by Defensive Runs Above Average?

Anyway, can we talk about the Luke Gregerson trade next?”

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