Revisiting (And Ranking) The Moves Of The 2014-2015 Offseason

The 2014-2015 offseason was a time of great excitement, with the Padres shocking the baseball world by making several blockbusters in the span of a few months, rapidly assembling an on-paper contender. It’s been two and a half years since it all went down, so we’ve all read (or written) numerous postscripts. In a few words: it didn’t work out.

Anyway, I was listening to the Make the Padres Great Again podcast the other day, and Craig and John briefly touched on the Wil Myers-for-Trea Turner three-team trade, classifying it as the worst move from that period. That’s a fair take, but it got me thinking: which move was the worst? . . . were there any good ones? . . . maybe I should make a list.

This is not going to be a super exhaustive look, because, let’s face it, nobody wants that. Instead, I’m breaking down each deal with my proprietary “then, now, forever” method (sorry, WWE). “Then” is how we felt about the deal at the time. This is arguably the most important category, so it gets double the weight of each of the other two categories in the final calculation. “Now” is how the deal looks today, 2.5 years later, and “forever” is our best guess at how the deal will look to (alien) baseball fans in 2200.

Sticking with the relatively simple format, we’re just going with letter grades, from F to, uh, A+, with a C being a ho-hum, run-of-the-mill deal. Alright, here we go, ranked in reverse order (from the best deal to the worst).

8. Acquired Craig Kimbrel and Melvin Upton from the Atlanta Braves for Matt Wisler, Jordan Paroubeck, Cameron Maybin, Carlos Quentin, and a competitive balance draft pick

Then: B-
Now: A-
Forever: A
Overall: B+

What I thought at the time: I was kind of lukewarm on the deal, noting that Kimbrel was the best closer in baseball and that, with him, the Padres should be better lined up for a playoff run, but also that they were dealing away a lot of young prospects and putting their eggs in a basket full of older, pricier veterans.

It’s always dangerous to give up a bunch for a closer, unless that closer is elite, with years of control remaining, and you don’t really give up all that much.

Wisler was the big prospect here. While he rated well at the time, he was the most dangerous kind of prospect (the pitcher), and he’s turned into a non-factor in Atlanta. On the undercard, Maybin’s turned in some solid years since the deal went down, and he’s currently working on his finest season since 2011. On the other hand, the Padres rehabbed Upton’s value enough to at least get an interesting prospect out of him in Hansel Rodriguez, although they still had to eat most of his hefty salary.

The big player on the Padres end here, of course, is Kimbrel. The Padres acquired one of the best closers in the league, and perhaps just as important, they acquired one of the best closers in the league signed to a long-term, team-friendly contract. Even after he had his worst year with the Padres in 2015, showing the first signs that he was indeed a human pitcher, they flipped him to Boston in the following offseason for a significantly better package than they gave up, one that included Manuel Margot and Logan Allen.

Maybe the Padres were just on the luckier side of the player development coin here, but their willingness to take on some money along with Kimbrel proved brilliant in the end, helping them get a bunch more out of Kimbrel when they dealt him in a pure trade—with no salary attachments—less than a year after acquiring him. Margot has a chance to be a cornerstone player, and Allen is creeping up on national top 100 prospects lists. Further, Carlos Asuaje might be a solid role player, and Javier Guerra, mired in a year and a half long slump, is still just 21. This was a great deal, one that netted the Padres a year of Kimbrel for what they hoped would be a pennant run, but ultimately should get them many years from players like Margot and Allen.

7. Acquired Justin Upton and Aaron Northcraft from the Atlanta Braves for Max Fried, Mallex Smith, Jace Peterson, and Dustin Peterson

Then: C+
Now: B-
Forever: B
Overall: B-

What I thought at the time: Like the Kimbrel deal, I mostly played this one down the middle. On the plus side, I noted that Upton was a good player headed into his age-27 season. On the down side, I didn’t like Upton, an okay defender, pairing with Myers (in center) and Matt Kemp in the outfield, and I was slightly concerned about the all-in push to win in 2015 at the expense of prospects.

Give the Padres some credit: of all the prospects they dealt in this manic offseason, most of them haven’t gone on to turn into legitimate big-league players. Smith might be the best out of this bunch, and it’s not clear yet whether he’s an everyday starter. Jace Peterson is like a younger version of the current Erick Aybar; he’s been a replacement level player in over 1,000 major-league plate appearances. Fried has major control issues, and he’s currently working on a 6.69 ERA as a 23-year-old in Double-A. Dustin Peterson had a nice year in Double-A last season, but he’s taken a step back at the next level this year.

Upton wasn’t great in San Diego, but he essentially performed within a rounding error of how you’d expect. Further, the Padres got the 24th overall pick in the 2016 draft when he left for free agency. That turned into Hudson Potts (or Eric Lauer, basically, who was taken 25th). I’d take Lauer, right now, over any of the prospects that went to Atlanta, and Potts is probably debatable. This was a solid move, then and now.

6. Signed James Shields to a four-year, $63 million deal

Then: C+
Now: B-
Forever: B
Overall: B-

What I said at the time: I generally liked this deal because the Padres rotation was something of a weak spot, in my estimation, and Shields should have theoretically improved it a good deal. Up to this point, they’d made so many win-now type moves, one more made sense, even if the reasonable price tag attached to Shields probably should have served as a red flag.

There were warning signs that Shields was past his prime (nobody wanted to sign him, his age, etc.), but he was still a relative bargain for a team that needed to add high quality depth to the pitching staff, and he only cost money. Shields had one year as a borderline league-average innings eater—when the Padres needed him to be more ace-like—and then he completely fell apart in 2016.

Where the Padres got smart is when they decided to trade him. (That is, other than throwing him under the bus on the radio just before doing so.) Instead of unloading him for peanuts as a salary dump, they sent him to Chicago with a boatload of cash and landed Fernando Tatis Jr. Maybe my Tatis love is coloring my view here, but that’s how you trade an aging veteran. Overall, there was pretty good process behind this deal, and when the results didn’t follow, the Padres made good by swapping Shields for an underrated prospect.

5. Acquired Brandon Maurer from the Seattle Mariners for Seth Smith

Then: C+
Now: C
Forever: C
Overall: C

What I said at the time: With Smith expendable in a suddenly crowded outfield, I liked Maurer as a good candidate to turn into a lights out reliever, although I was slightly weary of the position player-for-reliever swap. 

I almost completely forgot about this deal, to be honest. It was sensible at the time, but Maurer’s surface numbers have consistently been worse than his peripherals. Maybe that’ll turn around at some point, but it has sapped most all of the trade value he could have possessed right now. Smith’s fallen off some since the deal, but he’s still a league-average platoon bat with the Orioles. This is that ho-hum, run-of-the-mill deal I was talking about earlier.

4. Acquired Derek Norris, RHP Seth Streich, and int’l bonus slot from the Oakland Athletics for Jesse Hahn and R.J. Alvarez

Then: C
Now: C
Forever: C-
Overall: C

What I thought at the time: Like some of the other moves, I didn’t have a strong opinion. I noted that Norris looked like a solid offense-first catcher, and that losing Hahn “hurts a Padres rotation that isn’t as deep as you might imagine.”

Norris was solid in 2015, even if it’s not necessarily remembered that way. His offense dropped significantly, but he was still a league-average hitter. More so, his pitch framing was excellent, and he was worth 3.5 wins per BP. The bat completely collapsed in 2016, though, and not even solid framing could save that. Worse, there were apparently some clubhouse issues present, and now Norris is being investigated for domestic abuse allegations.

On the other end, Hahn has struggled with either health or performance in Oakland, and at times both issues have plagued him simultaneously. It’s hard to put this one anywhere but in the “meh” bucket; Norris wasn’t the right choice for the long-term catcher, by any means, but Hahn going the other way didn’t end up being something particularly regrettable.

3. Acquired Wil Myers, Jose Castillo, Gerardo Reyes, and Ryan Hanigan from the Tampa Bay Rays. Padres sent Jake Bauers, Rene Rivera, and Burch Smith to TB and Trea Turner and Joe Ross to the Washington Nationals

Then: C+
Now: D
Forever: D-
Overall: C-

What I thought at the time: I liked that the Padres were acquiring Myers as a buy-low guy, and that he was under control for a long time. I was also happy the Padres didn’t have to give up any of their marquee prospects/assets, although I obviously underrated Trea Turner.

I must face the reality that I was just wrong about this one, even though I think there’s a sliver of truth the idea that nobody dug Turner at the time of the deal quite like they do now. He was admittedly a fast-rising prospect at the time of the trade, and he’d come off a scintillating full-season debut at Fort Wayne, OPSing .976 in 46 games as a 21-year-old. Even then, however, the scouting consensus was more that he profiled as a speed-first threat, and that he had some holes in his swing and a decent shot to eventually move off shortstop.

Instead, Turner continued to tear up the minors and then showed an unforeseen power spike in his big-league debut last year, homering 13 times (with 35 total extra-base hits) in just 324 plate appearances. He also has snagged 70 steals in his first 168 major-league games, and he’s played both shortstop and center field.

Turner’s bat came back to earth this season before he went down with a broken wrist, but he still looks like a bonafied star even if that 2016 output ends up something of an aberration. To add salt to the wound, Bauers is a 21-year-old first baseman in Triple-A and Ross still has a chance to be a league-average starter.

Myers is the elephant in the room here. He’s got to be about the most inconsistent consistent hitter you’ll find, as he’s working on his third consecutive 115 wRC+ season despite seemingly always working on an extended hot or cold streak. We’re getting to the point where dreaming on a whole lot more from Myers is mildly unrealistic; he’s a good yet not great hitter, and he’s proven that over 2,000 major-league PAs. The problem is that he’s moved all the way to the wrong end of the defensive spectrum, and it doesn’t look like the base running and defensive value he flashed in 2016 is going to stick.

There’s still a smidgen of upside with Myers, of course. He’s only 26. He has the kind of raw hitting tools that can impress in spurts, and he could potentially benefit from some mechanical adjustments. He might be able to switch positions again, although a trap door will spontaneously open if he gets too close to center field.

Overall, you’ve just got to squint a lot more to see a future star here than with Turner, and Bauers and Ross only pile on. This one could end up being defensible at the time but disastrous in the long run.

2. Acquired Will Middlebrooks from the Boston Red Sox for Ryan Hanigan

Then: D+
Now: D+
Forever: D+
Overall: D+

What I thought at the time: “Middlebrooks possesses Right-Handed Power, but his approach at the plate makes batting practice the only place where he can show it off.” I didn’t like this deal in part because I didn’t much believe in Middlebrooks’ chance to rebound and in part because I thought Hanigan was too much to give up for the small percentage chance that he would.

I still find it amusing that Middlebrooks, who was coming off a 72 OPS+ in 2013 and 2014 combined, was always included whenever anyone mentioned the big-name players the Padres were acquiring back in the Rockstar GM period. Ultimately this was just a swap of down-trending assets, with the Padres taking a shot that Middlebrooks would recapture whatever made him good in his rookie season in Boston and at times as a prospect.

It didn’t work out, which isn’t surprising. Turns out Middlebrooks just didn’t have the kind of pitch recognition required of a major-league hitter. The reason I rated this worse than a pure C: the Padres were actually relying on Middlebrooks to play third base on a contending team. They gave him an 83-game audition, over which he barely OPSed .600 and provided just passable defense. Acquiring a post-hype prospect like Middlebrooks is never a bad idea when you’re rebuilding. But when the games matter and the left side of your infield is Middlebrooks and Alexi Amarista, maybe your playoff push was too haphazard.

For what it’s worth, Hanigan was pretty much toast at this point. Give the Padres credit for recognizing that.

1. Acquired Matt Kemp, Tim Federowicz, and cash from the Los Angeles Dodgers for Yasmani Grandal, Joe Wieland, and Zach Eflin

Then: D-
Now: F
Forever: F
Overall: F

What I said at the time: I wrote about this deal three times in the span of nine days, with two articles coming before the trade even happened. It culminated as such:

“If it’s a baseball trade, then it’s a disappointing start to the Preller era, as the Padres made exactly the opposite kind of move they should be making, dealing an underrated, undervalued youngster for an over-hyped older player to, at best, marginally improve the team. But if this deal is a clue that there’s going to be constant meddling from the business side of the Padres front office in baseball transactions—that the Padres are too worried about making a splashy belly-floppy type move to squelch Twitter angst instead of allowing a smart front office to build a consistent winner—then there’s really no worse scenario than that.”

Looking back, I might not have been harsh enough on this deal, and I was its toughest critic this side of Dave Cameron. It was almost an impossibly hard to comprehend trade, from any way you want to slice it, and it still is today. I know, I know, Grandal had the PED stigma and maybe he wasn’t the most popular guy in the clubhouse. That’s something a good team moves beyond.

In the end, this deal somehow turned out even worse than it looked at the time. Kemp just didn’t bring his A-game to San Diego, and he actually got outhit by Grandal; that’s before even considering defense or their respective contracts, which are both important things to consider. Since the deal, Grandal has blossomed into an unheralded star with the Dodgers. By Baseball Prospectus’ WARP, which includes pitch framing, he’s has racked up 13.2 wins in two and a half seasons. Kemp had to be dealt away to Atlanta in a swap of contracts neither team really wanted.

Oh well. If there’s one positive here, it’s that this deal was likely pushed by Mike Dee and/or ownership. That doesn’t absolve A.J. and baseball ops, but it takes some of the sting away, especially since the rebuild has been mostly positive so far.


This is the report card of a moderate slacker with a keen interest in one subject area.

I hope I’m not sugarcoating these deals. It was obviously not a good offseason, and the overall plan wasn’t well thought out. But I think there’s an argument somewhere here that with just some moderate adjustments, things could have turned out differently. If the Padres could have found a way to have stuck with Grandal, not acquired Kemp, and instead used someone like Hahn to get a legit third baseman, this might have been a playoff-ish team.

They didn’t do any of that, of course. A big part of the reason why this offseasonand the subsequent 2015 seasonis remembered with such criticism is because it all started off with that indefensible Grandal-for-Kemp deal, and that’s the reigning, defending, and undisputed worst move of the era. The Turner-Myers trade was probably worse than I thought at the time, and it could be one that hurts for a while. On the plus side, the Kimbrel trade(s) were legitimately good, and prospects like Margot, Allen, Tatis, Asuaje, and Potts all rose out of the aftermath of this offseason. Further, most of the players the Padres sent away, outside of Grandal and Turner, have generally disappointed or not yet taken off.

There were plenty of bad moves here, and in a big picture sense, the plan left a lot to be desired. But if you’re in the glass-half-full kind of mood, there were glimpses of player-evaluation skills from Preller & Co. on display, from finding a Tatis in the weeds to largely picking the right prospects to deal. It was a failed first attempt to build something, but more than half the deals were either defensible or relatively good, and the offseason on the whole wasn’t quite as destructive as the current narrative might indicate.

At the very least, it could have been even worse.

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  • filbert10

    Ahh love this article. Interesting to look back, and would be fun to re-review in another year or two. I do think that the $$$$ parts of these deals are being all but ignored. To give the Shields signing a B-/B, even though we got Tatis, really ignores the amount of $$$$ we had to pay ChiSox to get a prospect. I’d give the Shields signing a D or F.
    Even the Justin Upton deal. What did we pay him, $16M or so for one year? I’d give that one a C or D, not a B-/B. (And they could’ve traded him mid season for Fulmer..ouch!)
    Preller needs to thank management for allowing him to throw money around like that. It’s made a lot of these deals more palatable on the surface.

    • Eric J Chun

      Good point. Other money that shouldn’t be ignored is Quentin’s salary in the Kimbrel/Mupton swap, which cancels out the money eaten later on Mupton’s contract, making the Hansel Rodriquez acquisition a pure positive.

      • Pat

        Quentin doesn’t cancel out anything. We saved $8 million on the last year of his contract, nut paid Kimbrel $9 million. We also sent Maybin and his $7 million over, but then paid Mupton, who was basically the same player as Maybin, more than twice as much, plus another $16 million this year. IMO it was a horrendous trade at the time taking on a lot of salary to acquire a one inning reliever for a team that didn’t need one. It seemed to be based on a bad misreading of the teams ability to contend.

        They were quite lucky to have it work out as well as it did after the fact by being able to move Kimbrel for an excellent return, and getting better than expected production from Mupton. This doesn’t make the trade any better, they just got lucky that a bad trade in terms of process worked out for them

      • “IMO it was a horrendous trade at the time taking on a lot of salary to acquire a one inning reliever for a team that didn’t need one. It seemed to be based on a bad misreading of the teams ability to contend.”

        I don’t agree here, at all really. Obviously in retrospect this team stunk up the joint, and there were always holes present. But the projections had them around the low to mid 80s in wins before the Kimbrel trade (I believe), and smart baseball writers like Ben Lindbergh were picking them for a wild card spot.

        For a team that had done so much to try to turn into a contender, and for a team that genuinely thought it was a contender, this was a fine move IMO. It’s easy to look back on any of these moves and laugh knowing what we know now.

      • Pat

        That’s perfectly reasonable. Rating trades, and teams, is highly subjective after all. I don’t want you to think I’m going 20/20 hindsight on you. I hated the trade at the time and I’ve never changed on that. Partly it’s due to my opinion one inning relievers are way over valued, but I imagine also partly due to the whole offseason which had preceeded it. I thought it was foolish and shortsighted, I was not at all of the opinion we had made good moves, short term or long term.

        I can see why some might have thought the team could contend for a wild card, but that’s not really the time to make a move like they did for Kimbrel, IMO. There were definitely signs the team could have issues. They were weak up the middle, which is not generally true of strong teams. Sure catcher was solid with Norris, but Gyorko was not a good 2B and had struggled badly at the plate in 2014. Short was to be some sort of combo of Amarista and Barmes. Myers was not going to be able to handle CF in Petco, particularly with Kemp in RF next to him. None of that is hindsight.

        Speaking of Kemp, he shows the weakness extended beyond the middle of the diamond. Regression offensively should have been expected from him, and as good as he’d been at the plate the year before, he’d given it all back defensively. I never believed Middlebrooks was going to hit. Alonso I still felt could hit enough to be OK at 1B with his glove, but coming off two consecutive injury plagued years should have been a warning not to place too much faith in him. Again, none of this is hindsight. The infield was quite likely to be a mess, and the OF defense was pretty much guaranteed to be a mess. Even offensively it would have been wise to be sceptical of the offense of Myers and Kemp, given the former’s struggles the year before, and the latter’s age and injuries.

      • That’s fair. I agree with a lot of your points, even though (outside of the Kemp deal) I wasn’t nearly as down on these moves as you at the time. I didn’t average out my “then” grades, but if you weight them by importance of the deal, they’d probably come in somewhere around a C. So I didn’t love them, but I thought overall it was a solid shuffling of players.

        I didn’t think the moves were great, by any means, but the roster still looked like something of a contender to me, warts and all. I think the Kimbrel trade was very good either way because they took on some money to give up less, and Kimbrel was under control for a long time. As long as he didn’t get hurt/perform terribly, they probably knew they could eventually get back more for him in trade, with the way teams view relievers.

        It just feels like things could have broke differently. Kemp could have hit like he’s hit in Atlanta. J. Upton and Myers could have taken steps forward offensively. Gyorko could have been the hitter we thought he could be. Shields could have posted a 120 ERA+, etc.

        But, yeah, overall you obviously ended up being right, and some of the concerns I think we all had (Kemp, the infield, outfield defense, etc.) ended up doing them in.

      • Pat

        I think the shocker was the starting pitching really didn’t live up to expectations. Looking at a front four of Shields, Ross, Cashner, and Kennedy you would have expected better.

        And I was sure wrong in the value of Kimbrel given what he brought back. Wow!

    • Thanks, and yeah, good point. I’m probably too high on that Shields deal in terms of a grade. But I guess I wanted to reward the Padres for what I thought was pretty solid process. At the time, the Shields signing was pretty solid, especially in the context of the rest of the offseason. And then, once he stunk, they realized he was a sunk cost and paid to get rid of him *and* also add a solid prospect. There’s so much money in the game right now; I don’t want to necessarily punish a team for spending it, especially when it wasn’t really a bad move at the time.

      Same thing with Upton. That’s peanuts these days in baseball dollars. Fair point on the idea that they could have traded him at the deadline for a good return. So yeah I could see that more in the C/C+ range, but overall it was a decent move to add a star at a price that now looks pretty light.

  • ballybunion

    I like the ‘forever’ grade, since time and distance can turn a sow’s ear into… a gag gift, most of the time, but sometimes something better. The one thing I was thinking is that Preller took the measure of the Padres farm, especially the upper level pitching, and decided to tear it down and rebuild.

    The Moorad/Byrnes philosophy of high floor, middle upside prospects was most likely to keep the team a low-midlevel achiever, with a lucky 2-3 year contention window per decade, and I liked Preller’s emphasis on shoot for the moon talent and lots of it. Preller basically traded those midlevel guys for veterans he could flip, and for the most part, he ended up with more high upside than he had originally.

    I think Preller had other pressures (Mike Dee and Ron Fowler) to deal with, and we may never know why some of the moves you identified as the worst were made. I suspect Preller wasn’t entirely, or even mostly at fault, but the buck’s on his desk.

    • That’s about how I see it. There were major missteps in the ’14-’15 offseason, but I think some of the moves weren’t all that bad in isolation, plus Preller and co. have rebounded about as well as you can expect from it. The Padres have a better system now than they’ve had in years, and it’s (arguably?) deeper as it’s ever been.

  • Sac Bunt Chris

    One aspect of the Myers/Turner deal that Dustin touched on but I think gets overlooked is the relative risks of each player. Part of what the Padres were paying for with Myers was that he’d already seen success in the majors. You have to pay a premium for that, which the Padres obviously did, but it’s easy a few years later to forget how valuable that was.

    • Yes, this^^^ I should have said as much, but I definitely agree with it.

    • Pat

      That’s pretty generous. Myers had success as a rookie, true, but then fell on his face as a sophomore AND had a wrist injury which has been an issue for him even after the trade. And it was not Myers for Turner but Turner AND Ross. Not a good trade at the time and worse now that Myers is a 1B