In the twenty-first century, Major League Baseball’s front office personnel had a major breakthrough in pop culture relevance. With the enormous popularity of Michael Lewis’s book Moneyballgeneral managers became easily identifiable avatars for fans, particularly sabermetrically-inclined fans. The rising popularity of franchise modes in EA Sports video games, not to mention Baseball Mogul or Out Of The Park computer simulations, gave fans the (false) sense that while they would never crush a 500 foot home run off Roger Clemens, they could wheel and deal with the best of them.

For the first eight years of the 21st century, the man making trades and signing free agents for the St. Louis Cardinals was Walt Jocketty, and since then, it has been John Mozeliak. And each had a reputation for making fantastic trades to improve the Cardinals.

In the case of Mozeliak, a few recent trades have tarnished his reputation. To a degree, I would dare say this was an over-correction (I’m not losing sleep over trading an extremely blocked first base prospect for the 2019 team’s best reliever, nor over trading an outfielder who has below-average offensive and defensive metrics who is perceived as better than he is because he emerged from the razor-thin depth of the Cleveland Indians). As is so often the case, I would make the case that while Mozeliak’s worst moves aren’t as bad as they are perceived, his best moves, as well as the best moves of the Jocketty era, have been a bit exaggerated.

I took a look at six trades this century, three from Jocketty and three from Mozeliak, from the perspective of the other team involved and pondered their feelings on the transactions given a healthy dose of retrospect.


2000: Anaheim Angels acquire Kent Bottenfield and Adam Kennedy for Jim Edmonds

This trade is usually viewed through the lens of Bottenfield, one of the last vestiges of the “guy gets a bunch of wins and has a clearly anomalous season and some GM freaks out” era, and Edmonds, who became a historically great St. Louis Cardinal. But the real key to the trade for the Angels turned out to be, and likely always was, Kennedy, a highly-regarded second base prospect.

The Angels traded Jim Edmonds, a clearly talented but disgruntled and oft-injured star, with one year until free agency, and the 70-92 record from 1999 made it seem like it was time to get what they could for Edmonds. The Angels improved by 12 wins in 2000, and Adam Kennedy played 156 games. But the real breakthrough came from the guy who replaced Jim Edmonds in the outfield, Darin Erstad, who was an MVP-caliber player worth 8.3 WAR. Erstad regressed in future years, but Edmonds wasn’t likely to be there anyway.

In the meantime, Adam Kennedy kept improving, and he was a 4.6 WAR starter for the 2002 Angels team which won the World Series. From 2002 through 2005, Kennedy put up no fewer than 3.3 WAR—solidly above-average. None of this is to relitigate the trade from the Cardinals perspective—Jim Edmonds was a superstar in 2000 and the team used their exclusive negotiating window to sign him to a favorable extension. But this was a mutually beneficial trade that arguably benefited the Angels more.

2002: Phillies acquire Placido Polanco, Mike Timlin, and Bud Smith for Scott Rolen and Doug Nickle

The loss of Nickle was basically meaningless, but Scott Rolen was an established superstar already. But by the time the trade was made, Rolen was only under contract for another two months and the Phillies were 9.5 games back of a playoff spot. It was a known fact that Scott Rolen wanted out of Philadelphia, so re-signing wasn’t an option. It was just a matter of getting what you could for him.

Placido Polanco might be the most under-appreciated 40+ WAR player of all-time: he isn’t and shouldn’t be a Hall of Famer but he’s WAY closer than most people would guess. Polanco was worth 2.3 WAR in the next two months with the Phillies (less than Rolen, but more than the Cardinals could’ve reasonably expected for Rolen). He had a solid if not spectacular 2004, and in 2005, the Phillies flipped him for veterans Ramon Martinez and Ugueth Urbina. He apparently liked Philly more than Rolen did, as he later re-signed a three-year contract to start for (two) all-time great Phillies teams.

Bud Smith and Mike Timlin turned out to be nonfactors for the Phillies—Smith never again pitched in MLB and Timlin became a free agent after 2002 (though he did pitch fairly well for them)—but Polanco became a legitimate big-leaguer. It may not be an incredible return if you just think of the alternative as “Scott Rolen”, but this was firmly above-average salvage value.

2003: Braves acquire J.D. Drew and Eli Marrero for Jason Marquis, Ray King, and minor leaguer Adam Wainwright

The most significant Atlanta Braves Thing in the franchise’s existence in Atlanta isn’t their 1995 World Series title; it is their 14 consecutive division titles. It is an unparalleled level of success—the Dodgers have the longest active streak, one which seemingly has lasted forever, and they are only halfway to what the Braves accomplished. And that streak is arguably shorter if they don’t make this trade.

The Braves were trading two pitchers who, based on 2003 results and their incredible depth, may not have even made the 2004 team in Marquis and King. And in return, to fill the void left by the loss of Gary Sheffield, the Braves acquired one year of J.D. Drew, who responded by having the best season of his Hall-of-Very-Good career. By WAR, he was worth 8.3 wins. Eli Marrero, a smaller but not insignificant part of the deal, was worth 2.3 WAR. The Braves won the division by 10 games, a comfortable margin which is nevertheless a tad smaller than the combined WAR of the former Cardinals. The Braves didn’t have an abundance of better than replacement level outfield depth—it is not an unreasonable conclusion to say the trade made the difference.

Now, does that mean losing out on prime Adam Wainwright was worth it? I don’t think so. Plus, Wainwright probably makes the playoff difference for the Braves in 2009. But dare I say the 2004 playoff appearance, because of sequencing, mattered more? I still think it’s a not-good trade for the Braves but it’s not a disaster, either.

2009: Athletics acquire Clayton Mortensen, Shane Peterson, and Brett Wallace for Matt Holliday

This trade could’ve been an absolute disaster for the Cardinals, who traded three prospects, including top prospect Brett Wallace, for a rental. As it turns out, even if you keep in mind only Holliday’s 2009 accomplishments and not what he did after signing a market-rate extension that off-season, it worked out well—Holliday was awesome down the stretch and the prospects didn’t live up to their hype.

As for the A’s, Holliday was as good as gone (giving up Carlos Gonzalez and Huston Street to the Rockies to get him in the first place didn’t go so great), so they had to get something. Could they have gotten more? Perhaps. Mortensen only played in seven games before the A’s dealt him for a dead-end prospect; Peterson only managed a cup of coffee before he was waived; Wallace was flipped the next off-season for Michael Taylor (not to be confused with Washington Nationals outfielder Michael A. Taylor, who is much better than the guy they got). The A’s lost the trade in the sense that they could’ve traded Holliday for something—anything—else.

2014: Red Sox acquire Allen Craig and Joe Kelly for John Lackey and Corey Littrell

Littrell stalled out in AAA and wouldn’t have likely made the Red Sox, either. The major loss turned out to be the veteran John Lackey, less because of his 2014 performance—he pitched well down the stretch but the Red Sox were in the midst of a lost 71-91 season—but his 2015, where Lackey made a league minimum salary and was the Cardinals’ Game 1 playoff starter after a triumphant, 100-win season.

But as it turns out, the Red Sox weren’t much better in 2015, winning just 78 games. Lackey makes them better; he doesn’t make them a playoff team. An interesting, unanswerable wrinkle in all of this is that the compensation pick the Cardinals received for John Lackey turned out to be top prospect Dylan Carlson, but what are the odds the Red Sox make precisely that pick? Possible, but I would say unlikely.

Practically speaking, John Lackey wasn’t going to benefit a Red Sox playoff run, barring a re-signing. And as it turns out, Allen Craig was more toast than even the most cynical anticipated. But the actual cost of his contract meant minimal to the money-printing Red Sox compared to the value provided by Joe Kelly. Kelly was a critical component to the Boston bullpen in 2017 and particularly in 2018, when he pitched six scoreless innings with ten strikeouts over all five games of the Red Sox’s World Series victory. This was a trade of mutual benefit in which each team precisely evaluated its needs and competitive windows.

2014: Braves acquire Shelby Miller and Tyrell Jenkins for Jason Heyward and Jordan Walden

The Braves, who spent much of the 2014 season as playoff contenders, began their rebuild quicker than most, and trading their star right fielder early in the 2014-15 off-season was a big part of this. Heyward, a Georgia native, seemed to have a good relationship with the Braves and vice versa, but a post-2015 extension for the rebuilding Braves probably didn’t make much sense for either side. Walden, a good reliever, immediately became a major injury concern, but even if he had stayed healthy, he was merely roster filler in Atlanta.

The Braves landed Tyrell Jenkins, a prospect who didn’t quite land but whom they later parlayed into Luke Jackson, a perfectly fine reliever on their current, first-place team. But most importantly they acquired Shelby Miller, who had a career-best 2015. And while the fact that Miller’s career soon fell apart would probably make the Braves wish they’d gotten more for Jason Heyward (or even just gotten the guy the Cardinals got for the Heyward compensation pick, Dakota Hudson), the Braves sold very high, acquiring their current starting shortstop in Dansby Swanson, three-time defending Gold Glove center fielder Ender Inciarte, and Aaron Blair, a top prospect who flamed out but is good reinforcement of how crazy this trade seemed even in the moment.

The Cardinals won this trade because it won them the NL Central in 2015 and serendipitously got them a member of their current rotation. The Braves won this trade because it got them two integral pieces of their astonishing young core.


This is the nature of 21st century trading. There are no dumb teams (well, maybe the Arizona Diamondbacks when they traded Swanson and Inciarte for Miller). One could argue the closest thing to a true swindle for the Cardinals this century was when they traded Dan Haren and others for Mark Mulder. But also, to swindle isn’t the point. The point of trades isn’t to pull a fast one—it is reckless to try that against a smart person. The point is to find ways to improve yourself that are agreeable to smart people. Largely, the Cardinals have done this.

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