Getting Crafty With A.J. Preller and an Intriguing Trade Partner

It’s difficult to question A.J. Preller’s creativity since he’s been crowned General Manager of the San Diego Padres. Praised effusively in the world of baseball after major off-season acquisitions and free agent signings headlined by Justin Upton, Matt Kemp, Derek Norris, Wil Myers, Craig Kimbrel, Melvin Upton Jr. and James Shields, Preller’s gamble hasn’t paid off. Yet parity in baseball this season is so precarious that we are seeing last-place teams resist the temptation to blow up their struggling, free agent-impending rosters with hopes that contention is still alive.

Preller took on risks that old-school GMs ordinarily would have shied away from, like shipping prospects outright that were on the brink of reaching the major leagues (i.e., Matt Wisler), or dealing young major leaguers on the brink of a breakout (i.e., Yasmani Grandal, who is becoming one of the premier catchers in the National League). In trading talent for talent, and considering the volume of Preller’a activity, there’s bound to be a strikeout on some trades. Of course, it wasn’t all bad; acquiring the controllable Wil Myers, still with far more upside than most 24-year-olds, and dealing a quad of youngsters for Justin Upton has more pros than cons. What’s most apparent, however, is that it’s the middle of July and San Diego is an essential seller, meaning that Preller is ready to show off his craftiness once again.

Shackled with a variety of bad luck, expectations gone south, and just plain horrific defense, San Diego sits eight games under .500, and only a game ahead of the last place Colorado Rockies. Matt Kemp is below replacement level in just about every category. He’s cost the Padres numerous runs on each side of the ball and is just average on the base paths. Using’s model of WAR, Kemp (-0.5) ranks as the 11th worst position player in baseball. Jedd Gyorko, although his five-year, $35 million contract wasn’t inked by Preller himself — like Kemp — has cost San Diego wins on the WAR scale ever since the deal was signed. Upton Jr. was acquired in a terrible contract to begin with, Kimbrel is a constant weapon in the back-end of the ‘pen, the inexpensive Myers and Norris are rightfully in the club’s future plans, which leaves James Shields as the final heavyweight contract that could be in the mix for one of Preller’s potential trade partners. The younger Upton, an impending free agent, has performed well enough to reel in for San Diego at least a top-1oo prospect in a potential trade. But in the final analysis, one is left with a struggling ball club with an increasingly hefty payroll and a host of untradeable players that hasn’t come close to playing winning baseball. Which brings us to our next subject: how to navigate a successful rebuild, or perhaps one that will bring positive dividends to the Padres and to another club.

The best resolution, sans Upton and Will Venable, or perhaps Joaquin Benoit too — all of whom will surely be dealt — is to generate some dialogue with teams that also have expendable players signed to unusually large deals as well. The Red Sox immediately come to mind as a logical trade partner for numerous reasons.  However, it seems futile to consider a deal with the Red Sox before considering the most significant obstacle facing Preller in starting the rebuilding process: convincing ownership that it is essential to fix the club now, even if it may impact the chances of signing future free, or keeping the fan base engaged in light of next year’s All-Star game, which will be hosted by San Diego at Petco Park.

Provided by Dennis Lin of the San Diego Union Tribune, lead investor Peter Siedler had this to say about the possibility of a rebuild:

“I think they’re largely unrelated subjects. First, we want to provide an exceptional All-Star experience for everybody. Obviously, as part of that, we hope we have multiple players participating in the All-Star Game, because that will reflect on a strong team. But our expectations are going to be high going into the next year as well as 2017 and every year beyond.

“It’s not in our DNA to have a fire sale and to tear down. It is in our DNA to make good business moves and good baseball moves. And organizationally, I think that’s what we expect to happen right now, next year, the year after and the years beyond.”

Take that as you will. I suppose Siedler isn’t opposed to dealing from the current San Diego roster, even if that means being thrown by another club similar to the Red Sox acquisition last July of Eduardo Rodriguez for Andrew Miller. But after advising Rangers GM Jon Daniels for roughly ten years prior to beginning his tenure with San Diego, Preller should be trusted  to take some risks just as he did this past off-season. There’s really not much to lose, and it’s tough to imagine Matt Kemp ever being the player he was believed to be when he was acquired. And despite some of San Diego’s hefty contracts, there’s a significant possibility of approaching the deadline with viable trade pieces that other teams would find attractive.

The best solution, however, might be a bad-contract-for-bad-contract swap. And the Red Sox quickly come to mind as the optimal trade partner. Going back to Matt Kemp, one of the worst players in the game in 2015, he would be considered with two other Red Sox players who also were inked to expensive deals. One of them, Pablo Sandoval, in fact was targeted by San Diego last winter before acquiring Matt Kemp. The other is Hanley Ramirez. Sandoval ranks as the second-worst player in baseball, costing Boston -0.8 wins on’s WAR scale, while Ramirez, eighth worst, has cost the Red Sox -0.6 wins, even while belting 19 homers. It seems, however, that most of Ramirez’s struggles have come defensively in left field, a notoriously difficult position to play at Fenway Park.

For Sandoval, his rapid decline is difficult to fathom, but we know he has struggled far more on defense than at the plate. The Red Sox showed an interest in Shields this past off-season as well, and it’s simply just speculation to envision San Diego dealing Kemp, Shields, and perhaps a couple of low-level prospects for Ramirez, Sandoval, and maybe a low-level player as well. But if Preller wants to be creative, and get talent, it’s going to have to come with taking on some ugly salaries. As with Preller, Ben Cherington, Red Sox GM, is in job-saving mode too, and his last major money-saving blockbuster (the trade of Adrian Gonzalez, Carl Crawford, Josh Beckett, and Nick Punto to Los Angeles) seemed to operate in Boston’s favor. Also, Preller and Cherington hooked up on the trade of Ryan Hanigan for Wil Middlebrooks, so perhaps they can work out something pretty unusual again.

For Preller, July isn’t going to be as easy a time to acquire talent as it was before he dealt away nearly all of the San Diego system last off-season, but he’ll definitely have some valuable pieces to work with. Perhaps the best way for him to start is to deal Upton, though it’s apparent that some major changes need to happen this month if San Diego has any hopes of being in contention for 2016.




5 Responses

  1. Gabriel Acevedo

    almost HILARIOUS that you would even entertain the notion or casual flirt with the idea of Preller trading Kemp’s, so called, bad contract, for Panda’s…are you effing kidding me?

  2. Boourns76

    This reads like it was written by Preller’s public spokesman. A FEW strikeouts? Preller’s whiffed on every single move he’s made so far! Some whiffs worse than others, but there hasn’t been a single move he’s made yet that has worked out. And somehow he seems to have forgotten that in Petco Park, outfield defense kind of matters (which is one major reason why the pitching staff has done so poorly despite putting up similar advanced statistics as last year).

    • Gabriel Acevedo

      To say that he’s whiffed on every single move/trade, is a lie…and you know it. So my question is, “why is any of what he did or didn’t do, so personal to you?…did he trade your kid?…or mother?…a next door neighbor?…your pet?

      Or are you annoyed because he was given a ton of leeway and levity to overhaul a team that actually needed someone with his “stones”?..and again, what’s it to you?

      You’re not looking at the bigger picture, because it doesn’t ‘sell’, the way immediate criticism does.

      The bigger picture is, the Padres probably didn’t isolate 2015 as the season that they make a serious World Series run…but they knew that it was CRUCIAL, and probably more important to say the things that “suits” say to encourage fans to “come back”…and “we want to win now”, did the trick.

      The lack of trust had gotten so bad here in SD, the owners had no choice but to sacrifice an overhyped, albeit, relatively decent farm system to acquire the ‘names’ that would get attention…the kind of attention that got them noticed at the winter mtgs, in San Diego. That was no accident. It was by design, for the most part…

      The moves we’re needed, but Preller was very honest about the mandate, Mike Dee and Fowler, gave him, regarding San Diego being put in the spotlight that the winter mtgs bring. It was business…but the trades helped the club, too.

      And finally, the Padres had no core group of players…We HAD NOTHING!…ADRIAN, was our core…and he did it with no help for almost 6 or 7 yrs, after Piazza and Mike Cameron left..

      So, if Preller needed to trade a whole lot of prospects (most of whom, who will probably be just serviceable), then so be it.

      It takes time for a team like this to gel. Preller knows that…his mentor, Don Welke knows it better than any of us…Logan White knows this…and Mike Dee knows it (he was an exec w/ Boston, as they rebuilt their brand and their teams leading up to World Series in 2004) They are fine with hits they’re taking, because it’s par for the course. But Preller did a brief interview on the Padres flagship station, yesterday I think.. and is quoted as saying he would have to be “completely blown away” to move Shields, Kimbrel, Norris, Myers, because as he’s said a million freaking times already, “they comprise a core group of players that we need on this team, moving forward”..

      He’s simply doing his job, to see what he might get for Shields….we see this happen, when teams put their franchise players on waivers, to see which buffoon will jump first to pick up a whole lot of money on that players’ deal..

      I know it’s easy to beat the Padres down…you guys love doing it, because it’s so easy to do. But do you invest this much criticism on how Boston effed up, giving a ton of money to “Fatso” and his buddy Hanley?… what you got on, Seattle?….and Miami?

      • Boourns76

        I’m also critical of Ben Cherington (although he’s done pretty well in developing players and exhibiting patience) and Jack Z (clearly a worse GM than Preller). Miami’s a different beast (although they’ve won a WS recently), and you also forgot Philly (worst GM in baseball). But I think we have enough evidence to determine that Preller is one of the 5-10 worst GMs in the league. He literally traded away almost your entire farm system to grab a bunch of guys who don’t play good defense, who had problematic offensive skills (Kemp declining, Myers injury-prone and not clear how good the bat is, Middlebrooks can’t make contact), etc. He seems to have forgotten that Petco is a big time pitchers park, and defense actually matters a lot there. As a result, it’s really not surprising that your pitching staff is doing so poorly despite putting up comparable advanced numbers.

        You realize that you now have a $109 million payroll and no prospects left in your farm system, right? How is this ship gonna get turned around? Can’t go out and buy a bunch of FAs (already did that), and can’t trade a bunch of prospects (did that). There’s no relief coming. Only good news for Pads fans is that Preller will be fired within 18 months ($10 million richer for having ruined your team), and you can move on to the next guy, who is very unlikely to be worse.

      • Gabriel Acevedo

        you sound “unhinged”…what are you panicking about, My God. After one half a season, there is no way that you or anyone else, can be so matter of fact about how bad they’re going to be next year or the year after that.

        I said in my last post, that this team was basically “a model”…something to start with. And they are going to add to it, and take from it. Whats important is that they have a core of controllable players.

        this team is not in horrible shape…and the spots that need “new bodies” can be filled. And one again, how many times does someone have to tell you that, THEY HAVE THE MONEY NECESSARY TO RUN THE TEAM!!

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