The Dawn of the A.J. Preller Era
We close out our coverage of 2014 with the arrival of the most important man in trading.
The Padres were in the midst of organizational change and had fired former general manager Josh Byrnes on June 22nd On August 6th, San Diego’s A.J. Preller Era began. Preller was named to the general manager position at the age of 37 (not 36, as his Wikipedia page has incorrectly indicated since April of 2018) but had already been a key figure in the Texas Rangers front office for a decade. He joined an organization “looking for stability” after burning through three prior general managers in the past five years. In one sense, they got it; Preller is still in the job today and his contract runs through 2026.
But “stability” is not the adjective that would make the top 100 of the A.J. Preller Era. “Trades” would certainly crack the top 10 even though it’s not really an adjective. We’ve previewed this event before because it’s impossible to hold back the excitement. The main character of Trades Ten Years Later in our first year has probably been Philadelphia 76ers GM Sam Hinkie, but we’re approaching his final act before he leaves the NBA in 2016. Our new main character is going to be A.J. Preller and we have at least ten years until his final act. His first act was an unprecedented binge of transactions that nobody has topped in the years since (except him, multiple times). In a span of 36 hours, Preller traded away 15 players and acquired 11 as part of an effort to transform the Padres from a cellar dweller to a serious contender in the NL West. This was Prellerpalooza (Act 1, Part 1).
We should explicitly spoil the ending: every one of these trades was bad for San Diego, some disastrous. A.J. Preller’s contribution to the literature comes mostly from ridiculous volume rather than specific transactional brilliance. By July, Preller was being accused of “destroying the San Diego Padres in a manner of months.” After looking woeful to start the season, the Padres would scrap the notion of contending and pivot to a long-term rebuild that lasted the remainder of the 2010s. You are about to watch a man issue a challenge in a game of Russian Roulette, immediately blow out his brains, and then carefully pile them back into place before going about his day.
December 18, 2014
San Diego Padres receive: Derek Norris, Seth Streich
Oakland Athletics receive: Jesse Hahn, R.J. Alvarez
This was officially the first move of Prellerpalooza (even if another larger trade had been “agreed to” a week earlier) and it certainly ended up being the most gentle. In fact, there’s nothing in this trade that requires a radical departure from things we’ve talked about before. The Oakland A’s were trading away contributors from their 2014 roster, which has been a central theme of the last couple of months. Jesse Hahn and R.J. Alvarez had joined the Padres recently enough that we already wrote about the trades that brought them to town. This one is easy!
The star of this trade was Derek Norris, a 25-year-old catcher who had just made his first All-Star team in Oakland after a career-best season. All of the performance that went into that All-Star selection took place in the first half of the year, and a much quieter second half suggested that there were reasons to be skeptical of his long-term upside. Norris would still make a league-minimum salary in 2015 and therefore was ahead of the typical timeline for Oakland A’s to be traded away, but this would quite possibly be their last chance to trade “All-Star Derek Norris” instead of “Derek Norris.”
The last time we talked about Jesse Hahn, he slid in the draft with injury concerns, fulfilled those concerns by receiving Tommy John surgery, and then got traded from Tampa Bay to San Diego. His 2014 started with strong performance at AA and ended in the big leagues, where Hahn threw 73.1 innings across 14 appearances (12 starts) and was worth 1.1 WAR. It is the best 2014 anybody could have reasonably expected from Jesse Hahn. Critically, he had transitioned from “intriguing pitching prospect” to “young MLB starter,” a transformative upgrade in perceived status.
The last time we talked about R.J. Alvarez, he was an electric relief prospect with a 0.33 AA ERA who was a controversial inclusion when the Angels traded him to San Diego in July. Since then, he had debuted in MLB and kept a 1.13 ERA in his first 8 innings. Slightly worse than 0.33, but excellent on any normal scale of performance.
These seemed to have been savvy outcomes for San Diego that could result in multiple years of future value. Instead, they’d be converted into present-day currency. In exchange for giving up two promising young pitchers with strong (and incredibly short) MLB track records, the A’s threw in a pitching prospect named Seth Streich. Streich wasn’t a particularly well-regarded prospect (not even the top Seth in the Oakland system), but had done nothing but execute as a starter in the low minors. Perhaps he’d be the next example of a promising prospect that the Padres would turn into a major leaguer.
Seth Streich never pitched in the Padres organization. It took until June 20, 2017 for the team to release him, with multiple stints on the injured list in the interim. By that point, Derek Norris had played a slightly disappointing 2015 season in San Diego, followed by a dreadful 2016 season with a corresponding trade to Washington that winter. The following spring, a non-pitching Seth Streich remained in the Padres organization but Derek Norris was cut from the Nationals. He signed with the Rays and continued to play poorly before he was released in June and suspended for domestic violence allegations in September. He did not play in MLB again.
Pretty bleak, and all the other trades are certainly worse than this one for San Diego. R.J. Alvarez threw 250% more MLB innings in 2015 than he did in 2014 (20.0 vs 8.0), but allowed 900% more hits (27 vs 3) and [UH OH]% more home runs (7 vs 0). He proceeded to drop out of the major leagues until a 2022 reemergence for one game, six years after he left the A’s organization. Jesse Hahn made sixteen starts in a solid 2015 season and was a disaster in his remaining two partial seasons in Oakland. When we last checked in on Hahn ahead of the 2024 season, he had signed a minor league contract with the Dodgers after not pitching at any level since 2021. Hahn didn’t make it back to MLB in 2024, but threw 50.1 solid innings in AAA, which is pretty good work after a multi-year layoff. He’s signed with the Mariners on another minor league contract and will try to make it back to the majors in 2025. Good luck, Jesse!
The Padres basically gave up one good MLB season in exchange for one good MLB season, and the one they got back was better. An unsatisfying if effective trade. The next trades are substantially less effective for San Diego and substantially more satisfying for us.
San Diego Padres receive: Matt Kemp, Tim Federowicz
Los Angeles Dodgers receive: Yasmani Grandal, Joe Wieland, Zach Eflin
We could have written about this one quite a while ago. This trade was agreed to at the Winter Meetings and subsequent trades were agreed to in its footprint, but wasn’t processed until the 18th.
The trade’s biggest star was the reason for its holdup. The Dodgers were emerging from a less-glamorous period in franchise history that included a 2011 takeover by MLB and bankruptcy filing, but one of the few bright spots was a homegrown star named Matt Kemp. Kemp was a standout baseball and basketball player at Midwest City High School in Oklahoma, bypassing a basketball scholarship from Oklahoma State to sign with the Dodgers after the 2003 Draft. Kemp quickly attracted attention as a prospect due to “his excellent overall potential and athleticism,” particularly after a 2005 season where he played center field in Hi-A while batting .306, hitting 27 home runs, and stealing 23 bases. The true five-tool player is one of baseball’s most exciting commodities, and Kemp quickly established his ability to flash all five tools by the time he took over as the starting MLB center fielder in 2008.
One of the five tools is “fielding,” and this is where our story starts to get complicated. Despite routinely stealing more than 30 bases, an increasing sample size of defensive metrics was starting to show that Kemp was not actually a good defender, despite his nominal role as a center fielder and the Gold Glove award he captured in 2009. The 2010 season provides a particularly stark demonstration — Kemp regressed some with the bat in his age-25 season, but was still 6% better than the league-average hitter. According to Fangraphs, this quality offensive output combined with Kemp’s atrocious defense rendered him a replacement-level player worth 0.0 WAR. According to Baseball-Reference, Kemp’s defense was awful enough to reduce his WAR down to -1.1.
It almost defies mathematics that a 25-year-old center fielder could play such poor defense that a .249/.310/.450 slash line with 28 home runs ends up being a sub-replacement season. For comparison, the 2010 Dodgers rostered another -1.1 WAR outfielder in the form of a 38-year-old Garret Anderson, playing his final MLB season. Anderson’s slash line was an anemic .181/.204/.271. He had nine hits for extra bases in 163 plate appearances and struck out 34 times. The Dodgers mostly used Anderson to pinch-hit and he was similarly dreadful when asked to play defense. If you trust these numbers, Matt Kemp’s defense in 2010 was such a travesty that it converted his value from that of an everyday centerfielder with a solid bat to that of a pinch hitter who couldn’t hit.
The most dangerous sort of data is that which the user believes to be complete information. Critics of advanced metrics claim that they remove the human element from the game, and they have the potential to be right, but only if analysts lazily discount the human element. Maybe the story is that the 25-year-old suddenly lost his athleticism, or maybe the story is that the biggest star of the biggest baseball team in Los Angeles preferred being a star to trying his hardest on defense. He was hanging out with rappers and spent most of the calendar year dating Rihanna. He was cool enough to remain a fan favorite and walk on water, with the adulation continuing even as his stats tailed off.
Like most men in a stable relationship, Kemp had become complacent, seemingly forsaking his own growth and development. But at the end of the year, Rihanna and Kemp broke up, relegating Kemp from “Los Angeles star” to the understandably lower tier of “Los Angeles baseball star.” Like most men exiting a stable relationship, Kemp attacked the 2011 season with uncommon vigor, treating each day as a unique opportunity to become a better person. While his franchise was descending into the financial abyss, Kemp reached his apex form. He came one home run away from a 40/40 season in an era where his 39 home runs were still good to lead the National League. The guy whose defense was bad enough in 2010 to render him sub-replacement level won a Gold Glove (and Silver Slugger) in 2011 as he led the National League with 8.0 WAR. He should’ve won MVP that season, but placed second in a voting decision that was unjustifiable at the time and aged even worse after the first-place finisher turned out to be a drug cheat.
After the breakthrough season, the Dodgers awarded Kemp with an 8-year, $160 million extension and he publicly announced his intention to eclipse not just the 40/40 mark in 2012, but the theretofore uncharted territory of a 50/50 season. He seemed to be doing just that after an electric April, where he won the first two National League Player of the Week awards, capped it off with National League Player of the Month, and historically stacked up with the best Aprils by any non-Barry Bonds hitter of the last 40 years.
We’ve talked about Matt Kemp as a potential five-tool player, with all five tools on display throughout 2011 and the first month of 2012. But some say there’s a sixth tool – health (I thought this was a common saying, but it was shockingly difficult to find a source?). Kemp had previously showcased this sixth tool with a lengthy streak of consecutive games played. As April turned to May, the streak started to wobble, with Kemp used as a pinch hitter on May 6 to manage a tight left hamstring and keep the streak alive at 393 games. After six more games, Kemp was placed on the injured list, ending his ironman era and moving into what would turn out to be a new and unpleasant phase in his career. When he returned from the injured list on May 29, he set a new and less impressive streak of two consecutive games before his hamstring flared up and forced him out of action again. Kemp made his second All-Star team, but couldn’t play due to injury. He returned to action after the break, but picked up one more injury in August when he crashed into an outfield wall while trying to make a catch in Colorado, eventually requiring offseason shoulder surgery.
This was a bad way to kick off a huge 8-year contract and was unfortunately indicative of what was to come. After missing more time with hamstring and shoulder injuries in 2013, Kemp added an ankle injury to the mix, which ultimately ended up shutting down his season and requiring another offseason surgery. Over the last two seasons, Kemp had played just over one season’s worth of games. In the meantime, outfield spots began to be filled by additions like Carl Crawford and Yasiel Puig, leading to speculation that Kemp (or a different outfielder) could be traded. As the Winter Meetings approached, a Kemp trade seemed so likely that his agent Dave Stewart announced he’d attend for the first time because of his “strong feeling” that Kemp could be traded. “I haven’t heard a player’s name floated around like that and something not happen,” Stewart would add, but after another week of rumors, the Dodgers confirmed to Stewart that Kemp would not be traded after all.
Even if he was still on the roster, the 2014 season made it clear that Kemp’s status in the Dodgers organization had shifted. He started the season on the injured list and mostly played center field on his return, but began to be used in left field towards the end of May. Trade talks continued over the deadline as Kemp grew increasingly unhappy with a part-time role in the corner outfield, but flashes of his old performance combined with his massive remaining contract and increasingly constant injury concerns made it impossible for any two minds to agree on appropriate value.
But maybe that’s just because the right executives hadn’t been hired yet. New Dodgers hire Andrew Friedman promptly expressed his opinion that “it’s most likely the best course of action to move one of” the expensive outfielders on the roster, hopefully in a permutation that resulted in upgrades at catcher. A.J. Preller was described by reporters as “all over the map” as he “furiously explored” offensive upgrades. By the beginning of December, the rumors centered on a swap that would send Kemp to San Diego (with some cash to defray the remaining $107 million on his contract) and young catcher Yasmani Grandal to Los Angeles. As the Winter Meetings got underway, other suitors for Kemp were gradually eliminated from the sweepstakes.
On December 11th, the trade was sufficiently completed for Dave Cameron to publish a Fangraphs post about what a disaster this trade was for the Padres (though much of his complaint was that the Padres weren’t ready to contend yet, an objection that A.J. Preller was still working hard to eliminate). Dodgers fans were upset by the potential move even if they understood it to be a rational decision. Over time, the full trade got reported, with the Dodgers sending Matt Kemp, $32 million, and Tim Federowicz to San Diego in exchange for Grandal and two pitching prospects, Joe Wieland and Zach Eflin. Federowicz was a fringe catcher in the Dodgers’ organization who typically played at AAA over the last four seasons and would theoretically replace Grandal as organizational depth in San Diego. He played no games for the MLB Padres before leaving as a free agent after the 2015 season, rendering his contribution wholly theoretical.
Yasmani Grandal was the centerpiece of this trade, a young switch-hitting catcher who was only available due to his numerous red flags. Grandal was born in Cuba but immigrated to Miami as a teenager, eventually being drafted 12th overall from the University of Miami by the Cincinnati Reds. Grandal was sent to San Diego as part of the trade for early-career Mat Latos, then had arguably the coolest-possible start to his MLB career in 2012 when his first two hits were home runs from opposite sides of the plate, a feat nobody had previously accomplished. Part of that, uh, might’ve been the steroids, as Grandal would receive a 50-game suspension that offseason and eventually be implicated in the same Biogenesis scandal that took down the fraudulent 2011 NL MVP. Grandal returned briefly in 2013 before his season ended with ligament tears in his knee. In 2014, Grandal had a pretty normal season that gave credence to the theory that he’d be a solid big leaguer if the rest of his career was similarly normal.
The two pitchers sent to Los Angeles had less pedigree than Grandal. Joe Wieland was a major leaguer, sort of, having made his debut back in 2012. But he required Tommy John surgery and didn’t make it back to MLB until September of 2014. He had thrown 39 innings and they weren’t terribly impressive. Eflin had been selected by the Padres with the 33rd pick of the 2012 Draft and he had posted strong professional results, albeit not with a ton of strikeouts. Before he would officially arrive in Los Angeles, the Dodgers had agreed to send him on to Philadelphia in a package that brought back new starting shortstop Jimmy Rollins, a trade that was also delayed for about a week longer than necessary as everyone waited for the paperwork to finish.
That delay turned out to originate from Matt Kemp’s physical, which revealed that he had arthritis in both hips. This was a tough addition to the malady list for the guy with a bum hamstring and recent surgeries to his shoulder and ankle, particularly when he was under contract for five more years. Perhaps wisely, the Padres requested that Los Angeles include more than the $32 million they had already agreed to send. The Dodgers called their bluff and said no. Perhaps unwisely, the Padres went through with the trade anyways.
There were two moments in time at which the Padres won this trade, both of which were on April 6, 2015 when the Padres opened their season in Los Angeles. Dodger Stadium gave Matt Kemp a standing ovation in his first at-bat in a new uniform, and he hit an RBI single to give the Padres a 1-0 lead. The second moment came in the fifth inning, when Kemp hit a 2-run double in his third at-bat to reclaim a 3-2 lead. At the halfway mark of opening day, the Padres were leading the Dodgers and Matt Kemp was responsible for all three RBI.
The Padres would go on to lose the game 6-3 and the margin of defeat increased from there. Kemp would only play 254 games in San Diego – not because of injuries, but because the player and team were such a bad combination that they shipped him to Atlanta at the 2016 trade deadline. He was worth 0.7 WAR for the Padres in that time. We’ve just discussed the first of four trades that would involve Matt Kemp during his career, three of which included the Dodgers as a participant. The Dodgers somehow managed to win all four trades, even the one that was just between San Diego and Atlanta.
Joe Wieland’s remaining MLB career consisted of two more starts in Los Angeles and one in Seattle, all of which were successively worse than the bad baseline he had set in San Diego. Zach Eflin turned out to be a pretty decent starter in Philadelphia while Jimmy Rollins had one mediocre season in Los Angeles, so the Dodgers lost that leg of the deal, but apparently I’m relegating all discussion of the Jimmy Rollins trade to a footnote in the A.J. Preller special. The trade effectively boils down to Matt Kemp for Yasmani Grandal and it doesn’t require any advanced analysis to conclude that the Dodgers got the better of the swap. Grandal spent four seasons in Los Angeles, making the All-Star team in his first year and helping the team win pennants in the latter two. His bat was above average in all four seasons and he was worth 10.4 WAR according to Baseball-Reference. Obviously a winning trade.
We’re going to pull out the advanced stats anyways, because the scale of victory is open to interpretation. If we enter into the forbidden cult of catcher framing, we start to see how Yasmani Grandal ended up on an MVP ballot after the 2016 season.
Statcast’s publicly available leaderboard for pitch framing conveniently begins with the 2015 season, and in that time there are 80 catchers who have called more than 100 pitches and added at least one run worth of value with their framing.
11 catchers have added 30 runs or more of value, with reigning AL Gold Glove Cal Raleigh and perpetually reigning NL Gold Glove Yadier Molina each tied at exactly 30 (in the final 8 of Molina’s 19 MLB seasons).
Buster Posey is in second place at 65. Posey’s excellence at framing feeds into the Giants’ league-leading team total of 88 catcher framing runs since 2015.
Yasmani Grandal has 103 by himself, 68 of which came with the Dodgers. Sure, it’s easiest to be the all-time leader in a stat if they don’t start tracking it until you’re reaching your prime, but this is Steph Curry-esque dominance of a statistic that baseball teams were already prioritizing when the leaderboard began. If you’re a true believer in catcher framing, trading Yasmani Grandal becomes the sort of offense that would get a lesser executive fired. Fangraphs’ WAR formula is one such believer. The 10.3 WAR that Baseball-Reference attributes to Grandal’s Dodger years balloons to 20.9 WAR at Fangraphs, making Grandal the 12th-most valuable player in baseball for that four-year period and putting this in the conversation for most lopsided trade of 2014.
You know the best part about it? Yasmani Grandal cannot catch. He’s actually bad at catching. He led the league in passed balls in 2016 and 2017, pacing all of MLB over this four-year period with 43. He was a bit worse than average at throwing out baserunners. The Dodgers benched him during multiple playoff runs in favor of Austin Barnes due to his issues on the defensive end. As a Dodgers fan, memories of Yasmani Grandal catching are typically tinged with frustration at some form of ineptitude rather than wonderment at the unparalleled framing, and the fact that he’ll have something of a defensive-first reputation for his career baffles my lived experience.
But that’s why this perspective is helpful — Grandal was obviously a good player and the Dodgers acquired him in the first of four winning Matt Kemp trades. Why am I complaining? There’s still plenty of fireworks to enjoy.
December 19, 2014
San Diego Padres receive: Justin Upton, Aaron Northcraft
Atlanta Braves receive: Jace Peterson, Max Fried, Dustin Peterson, Mallex Smith
There’s no way to do Prellerpalooza justice and at this point I’m guessing the closest we’ll get is by making the longest post in Trades Ten Years Later history (editor’s note: confirmed). All of these names deserve more attention than they’re going to get. Zach Eflin has thrown 1000 MLB innings and received Cy Young votes and got like three sentences in the last trade discussion, plus one more just now. But that’s sort of the point; Prellerpalooza is about gluttony, ideally in the most impracticable fashion possible. Pour a bottle of 30-year single-malt into a 2-liter of Cherry Coke Zero. Order an extra-large pizza with truffles and caviar. Deep fry a Lamborghini.
We’ll start with Justin Upton, who has a brother named B.J. B.J. set a difficult pace for his younger brother to keep up with when he was drafted second overall by the Rays out of Greenbrier Christian Academy in 2002. On August 2, 2004, B.J. Upton made his MLB debut 19 days before his 20th birthday, becoming the youngest player in Tampa Bay history and the youngest big leaguer to play in the 2004 season. Apparently, this was good motivation. Justin Upton was drafted first overall by the Diamondbacks out of Great Bridge High School in 2005, besting his older brother by one pick. The Uptons became the highest-drafted siblings in history and set a record that can be broken precisely one more time if a #1 overall pick has a sibling get selected #1 overall (probably this June). Then, on August 2, 2006, Justin Upton made his MLB debut 23 days before his 20th birthday, becoming the youngest player in Diamondbacks history and the youngest big leaguer to play in the 2006 season. The two Uptons are still the only 19-year-old hitters to ever play for these franchises.
B.J.’s adjustment to the big leagues was slow enough to put the brothers on similar career trajectories. Both were starters by the 2008 season and both hit their 100th career home runs on August 3, 2012. The two were set to be free agents in consecutive offseasons, but Justin signed a six-year extension with Arizona in 2010 that would keep him under contract through the 2015 season instead. The Tampa Bay Rays were obviously not going to do anything like that, so B.J. entered free agency and signed a five-year contract for $75 million with the Braves in November of 2012. Meanwhile, Justin’s contract extension turned out to be a poor measure of security, with his name appearing in trade rumors just one year into the six-year contract and never really disappearing. In January of 2013, Justin utilized a limited no-trade clause to block a move to Seattle, perhaps holding out hope that his brother could put in a good word to get him a job at his new company. The gambit worked; a couple of weeks later, Justin was traded to Atlanta and the two brothers were excited to play side-by-side in the outfield.
Working with your sibling can be a positive or negative experience, theoretically and empirically. Justin Upton’s first two seasons in Atlanta had been “pretty good” — he hadn’t hit the heights of his best Arizona seasons, but was one of baseball’s better left fielders. B.J. Upton’s first two seasons in Atlanta had been “wretched,” with his contract in the running for “worst free agent deals ever” as the 2014 season wound to a close. B.J.’s albatross of a contract still had three years to go, but Justin’s extension was about to run out. The Braves had already made decisions that rendered 2015 a rebuilding year and it made sense to commit to that philosophy by trading away the still-good Upton brother.
Upton represented a particularly puzzling acquisition for San Diego. Most of the players the Padres acquired in this binge wouldn’t be free agents for several seasons, but Upton would have just one year of control. The Padres were clearly trying to compete for the 2015 season, but it was going to require quite a leap to do so. This was a move that would not work out unless that leap was immediately successful. The front office didn’t seem to care, noting that they could recoup value by making Upton a qualifying offer prior to free agency. Fans didn’t seem to care, probably because this was the most exciting thing the Padres had done in the 21st century.
Along with Upton, the Padres acquired a pitching prospect named Aaron Northcraft who the Braves had selected in the 10th round five years earlier. He didn’t make it to the majors until 2021, by which point he had been released by San Diego, spent a season with Seattle, missed a season during the pandemic, and rejoined the Padres. He threw 8 innings and has a 2.25 career ERA that is likely permanent. Impressive stuff for a 30-year-old rookie, even if the 6.55 FIP suggests that Northcraft was wildly lucky to strand 12 of the 13 baserunners he allowed. Northcraft’s career is not one that should move the needle on an evaluation of this trade, but it’s a fun one. His 2.25 career ERA did happen and is better than most Hall of Famers. Duly acknowledged.
With Northcraft’s contribution discounted, all the Padres got was one season of Justin Upton. It was a good season — he was an All-Star and had 4.2 WAR, the best player on a San Diego team that went 74-88. Then he left as a free agent. The Padres selected a guy named Hudson Potts with the compensation pick. He never made the majors.
What did they give up in exchange for this Justin Upton season? Most immediately, they sent Jace Peterson, a glove-first second-baseman who made his debut in 2014. Peterson would be a regular during the rebuilding years endured by the Braves in the aftermath of this trade until he was non-tendered after the 2017 season. Next was Mallex Smith, a center fielder who had just stolen 152 bases in the two minor league seasons leading up to this trade. He would play a partial rookie season in Atlanta, contributing one WAR before being traded in January of 2017. Dustin Peterson’s Braves career consisted of two pinch hitting appearances (one strikeout, one flyout).
That left Max Fried, the highest-upside prospect in the trade. Fried was drafted 7th overall out of high school in 2012 and was one of the more promising left-handed pitchers in baseball entering the 2014 season. The future got a bit cloudier when he blew out his elbow 10.2 innings into the season, requiring Tommy John surgery from which he was still recovering at the time of the trade. He wouldn’t pitch at all in the 2015 season, but returned healthy enough to reach the majors in 2017.
I don’t think the dramatic reveal works all that well when the guy signed a $218 million contract a few weeks ago, but just in case it would have, Max Fried pitched so well in his time as a Brave that a different team just paid him $218 million after he became a free agent. He became a rotation mainstay in 2019 and has finished in the top five of Cy Young voting twice (5th in 2020 and 2nd in 2022). His 3.07 ERA is the 5th best in baseball since his debut among pitchers with at least 800 innings. Fried has made two starts against the Padres in San Diego and hasn’t allowed a run in the fourteen innings he’s thrown.
You’d probably rather have those years from Max Fried than the 2015 season of Justin Upton. But on the other hand, if Preller didn’t trade for Justin Upton, his upcoming trade to acquire B.J. really wouldn’t make sense (more on that in a few months).
San Diego Padres receive: Wil Myers, Ryan Hanigan, Jose Castillo, Gerardo Reyes
Tampa Bay Rays receive: Rene Rivera, Burch Smith, Jake Bauers, Travis Ott, Steven Souza Jr.
Washington Nationals receive: Joe Ross, Player to be Named Later (Trea Turner named on June 14, 2015)
There’s a through line to all of these trades (besides being horrible for San Diego). In 2014, and really only in 2014 to my memory, right-handed power was the hottest commodity in baseball. The perceived scarcity of right-handed power hitters was impactful enough that Atlanta expected to get a higher trade return for Justin Upton than the statistically superior and contractually similar Jason Heyward because of Upton’s status as a right-handed power hitter. I don’t recall what calamity was supposed to befall teams that didn’t have enough right-handed power, but nobody wanted to risk it.
So far, we’ve discussed the acquisitions of three right-handed hitters, all of whom hit double-digit home runs in 2014. Kemp and Upton each had hit more than 30 in a season in recent memory. These hitters would inevitably provide a jolt of right-handed power to a lineup that rocked an unfathomably bad .342 slugging percentage for the 2014 season, setting a bar of futility that was not surpassed until the 2024 White Sox limboed beneath it with a .340. San Diego only had four hitters reach the double-digit home run threshold in 2014 and the team leader in home runs from the right side was catcher Rene Rivera with 11. Rivera was a 30-year-old catcher who had his first run of extended playing time in 2014 and had four career home runs in five partial seasons before that year. He was not what people meant when they said “right-handed power.” He was also being actively traded away.
It was quite clear that Preller had no qualms with making big trades and several of these acquisitions would eventually be shipped elsewhere – perhaps the scarcity of right-handed power enticed Preller to try a mercantile role where he gathered right-handed sluggers to be sold later at a premium (sounds dumb, but we’re brainstorming). If that was the plan, it might not have been the best for the San Diego Padres, who played at notoriously pitcher-friendly Petco Park. Petco rated as a particularly bad stadium for right-handers to hit home runs, even after renovations to move the fences in after the 2012 season.
This is a three-team trade that looks more complicated than it was. The Padres basically traded four guys to the Rays for one young star and two minor prospects, plus the two teams swapped catchers for some reason (the aforementioned Rene Rivera and Ryan Hanigan, who the Padres would immediately flip onwards to Boston for Will Middlebrooks). Then, the Rays sent all the good prospects on to Washington to get their own right-handed power bat and kept the bad prospects.
The star of this trade was Wil Myers, making this the second-most shocking Wil Myers trade in history to this point. Myers was a 3rd-round pick in 2009, drafted as a catcher and converted to outfield shortly thereafter. He didn’t seem to be challenged in the minor leagues and was a consensus top-10 or even top-5 prospect in MLB when the Royals traded him to Tampa Bay before the 2013 season for James Shields and Wade Davis. The move was immediately scorned as an overpay for Kansas City and looked even worse after Myers was called up in June of 2013. Myers was so instantly good that he won AL Rookie of the Year that season despite only playing 88 games.
Winning a seasonal award probably bestows more standardized prestige than it really deserves, and the Rookie of the Year award is especially pernicious due to the smaller pool of eligible players. When Wil Myers goes from a top-5 prospect to Rookie of the Year, it validates the belief that he was going to be a good MLB player and cements him as a “young star.” The problem is that every league has one (and only one) of these winners. A couple of weeks before Wil Myers was called up, Yasiel Puig made his MLB debut and actually performed like one of the best players in baseball. He didn’t win the Rookie of the Year award, or come all that close, because Jose Fernandez was one of the best pitchers in baseball and maintained that performance since his April debut. There were about a half-dozen vote-getters in the National League who had better rookie seasons than Wil Myers, but none in the American League, so Myers got to be the Rookie of the Year. We just saw a similar phenomenon in 2024, where all three runners-up in the NL had a superior rookie season to the AL winner.
Since Myers was a cemented “young star,” a rough 2014 season was chalked up to the side effect of a wrist injury that took him out of action from the end of May to the middle of August. That probably didn’t help, but Myers’ performance had fallen off long before he missed time. His slugging percentage fell below .400 after his fifth game and only surfaced above that level one more time that season, ultimately settling at a putrid .222/.294/.320 slash line. The most similar offensive performance in 2014 came from the defense-first catcher Hank Conger. Instead of the scant package that we saw bring back Conger a couple of months ago, a trade of Wil Myers still managed to send real talent flying in all directions.
We’re like 6,500 words in and nothing has gone right for A.J. Preller and the Padres so far, and now they’re trading for a guy whose recent performance vastly underwhelmed his expectations. I already told you that all these trades went badly. There’s going to be at least one calamity here. Maybe the “wrist injury” that hindered Myers in 2014 was more ominous than believed, which seemed to be the case at first when he only played 60 games in 2015. But after a surgery and a transition to first base, Myers resumed everyday play during the 2016 season and made the first All-Star game of his career. Hard for this one to be a loss, especially considering that Myers wouldn’t enter arbitration until that offseason and was under team control through 2019. Norris and Kemp fell off and Upton was only around for a year, but Wil Myers seemed to be the rare example of A.J. Preller’s December to Remember resulting in the outcome he must have hoped for.
There are two stages to the calamity. One was the decision to sign Wil Myers to a contract extension that winter, the second of numerous occasions where A.J. Preller would award a player with the largest contract in Padres franchise history. Instead of going year-to-year at arbitration salaries through 2019, Myers was locked up through 2022 at a rate that seemed pretty generous, particularly when the salary quadrupled after the 2019 season. It definitely felt that way when Myers’ offense got worse instead of better in 2017, and then things got confusing that winter. In what I’m pretty sure marked the opening shots of The Second Act of A.J. Preller, San Diego signed free agent first baseman Eric Hosmer to the new largest contract in Padres franchise history. Myers had just played two healthy seasons at first base, but shifted to play most of his games at third base in 2018 and correspondingly got injured again, playing in just 83 games. Confusion escalated that winter when San Diego signed free agent third baseman Manny Machado to the new largest contract in Padres franchise history, pushing Myers back into the outfield. He stayed healthy in 2019 and was simply mediocre, registering as below replacement level despite getting into 155 games.
After the first attempt went poorly, the Padres were finally ready to compete again as they entered the 2020 season. This was also the offseason when Myers’ salary increased from $5.5 million to $22 million, rendering him something of a theoretical millstone on the team’s ambitions to compete. I’m not sure whether the fact that San Diego had club-record high payrolls each season makes this more or less impactful, but the all-encompassing treatment of Wil Myers as a franchise building block was the first calamity. You probably shouldn’t award record contracts if you don’t have to, you should get good value on the occasions you choose to do so, and you definitely shouldn’t turn your freshly extended player into a spare part just in time for his price tag to go up.
Realistically the Padres were happy to have Wil Myers. On the actual ten-year anniversary of this trade, MLB.com’s AJ Cassavell stole my idea and talked to Myers about his San Diego experience (interestingly just Myers, and not Matt Kemp, Justin Upton, or Derek Norris (or Aaron Northcraft or Seth Streich)). Cassavell describes Myers as “something of a fan favorite,” noting his unique role in franchise history as “the best player on some truly bad teams” as well as “a role player on some very good ones.” His penultimate act as a member of the team came after the Padres’ 2022 NLDS victory, when he and his wife went from bar to bar to buy shots for celebrating San Diego fans. His final act was contributing to a losing effort in the NLCS, after which his career consisted of 37 very bad games in Cincinnati. Myers notes that he has not officially retired “and never will,” but also mentions that he played 250 rounds of golf in 2024, so you should draw your own conclusions.
We’ll have to look elsewhere for our calamity and it will need to be fairly convincing. Everyone involved in the fringe three-team swap of Rene Rivera, Ryan Hanigan, and Will Middlebrooks was pretty bad for the brief remainder of their MLB careers, so no harm there. Despite the fact that Burch Smith already had major league experience in 2013, he didn’t make it back to MLB until 2018, at which point he was now a Rule 5 selection with the Royals. Immaterial. Jake Bauers made it to MLB in 2018 and was worth 0.5 WAR for the Rays that year before he was traded in the offseason. He’s been worth -2.4 WAR since that year. Immaterial. Nothing that flowed from San Diego to Tampa Bay was problematic.
The final segment of our trade is where San Diego gets into trouble, even though they weren’t directly involved. The Rays wanted to acquire their own version of right-handed power in this swap and targeted Steven Souza Jr. from the Nationals. Souza was demonstrably right-handed, physically large, and had slugged enough in the minors in 2013 and 2014 to suggest that he’d continue to be powerful in the majors. The catch was that he was doing this minor-league slugging at something of an advanced age and would turn 26 in April, calling into question whether the performance would hold up at the MLB level. Souza had nothing left to prove in the minors and could start to answer those questions in 2015, making him a valuable commodity for a Rays team in transition. They also added Travis Ott, a tall left-handed pitcher who didn’t throw very hard but might figure out how to do so someday. He did not; his professional career peaked with one three-run relief appearance at AAA. The Rays kept Souza around for two seasons that were decent and traded him away after the third was quite good.
In exchange, the Rays sent Washington pitcher Joe Ross and a player to be named later. Joe Ross was the Padres’ first-round draft pick in 2011 and the younger brother of Tyson Ross, a starting pitcher the Padres acquired after the 2012 season. Josh Byrnes must’ve had ambitions to combine the Ross brothers just like the Upton brothers, but it’s hard to get the timing right – Ross reached AA in 2014 and was still about a year from making the majors when he was traded elsewhere. Scouts hoped that he could be a mid-rotation starter in short order. The other player hadn’t been named at the time of the trade, but probably wasn’t significant based on our history with players to be named later.
I’m providing you with an absurd fiction that was technically true. Everyone immediately knew that Trea Turner was going to be named later and had a pretty good idea of when “later” would be. The PTBNL label implies a throw-in, but Trea Turner was likely a foundational piece in any trade for Myers. The reason for the obfuscation is that Turner was selected 13th overall in the 2014 Draft, and MLB rules prohibited players from being traded until one year after they’ve signed their first contract. Turner had signed on June 13, so was not eligible to be traded until the same date in 2015. But teams had six months of leeway before they were required to identify a PTBNL, creating a loophole as of December 13, 2014. From that point forward, teams could negotiate a theoretical Trea Turner trade that would remain unfinalized until approximately June 14, 2015. Lo and behold, Turner was officially sent from San Diego to Washington on June 14.
It seems unlikely that anybody had seriously considered the practical implications of this before December 13, 2014. The Padres had cut ties with Trea Turner and the Nationals had identified him as a piece of the future. It wasn’t really a stealth operation; Turner’s inclusion was widely reported in the media and both teams surely talked to him about it off-the-record. But rules were rules, and the rules were clear that Trea Turner was a San Diego Padre until June. So in March, he reported to his first spring training with the team and ranked as the third-best prospect in the Padres’ system. “He’s our player, and we put him here in big league camp to give him an opportunity,” A.J. Preller said about the 21-year-old Turner, even as everyone within earshot of those words knew that he was not really their player and would not have an opportunity with the Padres. “I’m not going to worry about something that’s beyond my control, I’m just going to go out and play as hard as I can and help my team win,” Turner deflected, leaving it ambiguous what “my team” was in this context.
Obviously it’s stupid, but it had the potential to be worse than stupid. Baseball is a competitive game where teams have gone to much more difficult lengths to sabotage one another. At the margins, it will necessarily be more difficult for the San Diego Padres to win a World Series if the Washington Nationals have a great shortstop. The “optimal” move for the success of the Padres would be to lock Trea Turner in a dark dungeon for the rest of his time with the organization or make him run Oklahoma drills before games in hopes that he never amounts to anything. At the time of the trade, Nationals GM Mike Rizzo said that he and Preller would “trust each other and do what’s right by the player,” but even perfect intentions wouldn’t eliminate the risk to this arrangement. What if genuine feedback from Padres coaches ends up being the opposite of what Washington would’ve taught him? What if a coach encourages him to be aggressive on the basepaths and he gets seriously injured stealing a base? What about the potential Padre of the future who’s spending two months on the bench behind Turner instead of getting his time to develop?
By May 1, everyone realized that this was horrible and should never happen again. MLB and the MLBPA agreed to change the rules and make drafted players eligible to be traded as soon as the World Series ends. Starting with the 2015 Draft, of course. Despite the fact that his circumstance obviously necessitated an immediate rule change, Turner was left languishing at AA Amarillo for six more weeks until he could finally join his team. Any harm seemed to be speculative – the Padres played Turner pretty much every day, and the Nationals kept him at AA for ten more games before calling him up to AAA. This was all ahead of schedule, and Trea Turner’s semester as an exchange student in San Diego can be remembered as a fun oddity with no hard feelings. Except, well…
This brings us to the second stage of the calamity. Trading for Wil Myers was totally fine, even if extending him was bad. Trading Jake Bauers, Burch Smith, and Rene Rivera for Wil Myers wasn’t a problem, and trading Joe Ross for Wil Myers didn’t hurt too much either. But giving up Trea Turner was catastrophic. He quickly became one of baseball’s best leadoff hitters, stealing bases with ease and playing quality shortstop defense. As Myers toiled in a down 2019 season before the big money on his extension kicked in, Turner was winning a championship in Washington. He was traded to the Dodgers in 2021 but also won a batting title that year, and he’s made an All-Star team in all three MLB uniforms he’s worn. His contract with the Phillies pays him $27,272,727 per year through 2033. He could plausibly make the Hall of Fame.
As an added treat, Turner became something of a power hitter, averaging 25 home runs per 162 game season and staking his own claim as a five-tool player. The right-handed Turner has 171 career home runs and passed Myers’ total of 156 earlier this year. Sometimes, the easiest place to find right-handed power is in the last place you look.
While A.J. Preller has been entertaining in the aggregate over the past ten years, this initial burst of activity was followed by a period of relative tranquility. There would only be one more franchise-altering trade in San Diego before the 2015 season began, which is more than a lot of franchises but substantially fewer than the Padres pulled off in these 36 hours.
There are obviously a lot of enduring lessons from Prellerpalooza, most of which involve considering what position players will play before you trade for them, but perhaps the most generalizable is the testament to clear-eyed perseverance. This post contains more transactional failure than many baseball GMs get to experience in a career, and when it became clear which way the winds were blowing, Preller adapted and shifted the organization into a hard rebuild. Admitting that you were wrong is never easy, particularly when it’s on such a public stage and in a manner that is costing your boss tens of millions of dollars, but Preller didn’t hesitate to do so (as we’ll see on numerous occasions in 2025 and 2026). He may be even better at turning unheralded amateurs into tradeable prospects, and before long Preller had signed contract extensions and gotten a bump in title and found new opportunities to go all-in. He’s in the midst of a quiet winter, but we can be confident that A.J. Preller always has something up his sleeve. Long live the king.