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Revisiting San Diego Padres A.J. Preller’s Curious Deals

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Faulty physicals netted Padres two top prospects

MLB: All Star Game-All Star Futures Game Jake Roth-USA TODAY Sports

At the 2016 trade deadline, San Diego Padres General Manager A.J. Preller made waves for all the right reasons. He acquired one of the game’s best pitching prospects, Anderson Espinoza, for breakout lefty Drew Pomeranz. A former first round pick by Cleveland, the 2016 All-Star was acquired in the off-season for disappointing first baseman Yonder Alonso, who would also coincidentally revive his career in Oakland with an All-Star 2017.

Preller also dealt the expiring contract of Andrew Cashner —who had an ERA almost reaching five — for Josh Naylor, the first round pick of the Miami Marlins the year prior.

The Marlins gave up on one of their few heralded prospects for half a year of Cashner, but also acquired Colin Rea at the further expense of pitcher Luis Castillo.

Turns out, Rea was taking anti-inflammatories for elbow discomfort and Preller didn’t think the information worth noting. The teams re-swapped Rea and Castillo and Rea would undergo Tommy John surgery. He’s out until 2018.

I guess mistakes happen, but the same thing happened in the other deal. A deal of true blockbuster proportions —involving an All-Star pitcher and a blue chip prospect— was also completed sans integrity.

Just like Rea, Pomeranz was taking anti-inflammatories for elbow pain and would be rendered a bullpen piece at best by September for the contending Red Sox. Major League Baseball offered Boston the chance to reverse the deal, but didn’t take it due to the trade deadline having passed and their hands now tied.

MLB: Boston Red Sox at New York Yankees Andy Marlin-USA TODAY Sports

The 28-year old Pomeranz also had two more years of team control. They stuck it out and hoped his medical troubles were behind him. (It looks like they were.)

A.J. Preller had had some disciplinary issues during his time assisting Jon Daniels with the Texas Rangers, but was nonetheless a coveted disciple and hired by San Diego in 2014.

For his shady transgressions, he would be suspended 30 days by Commissioner Rob Manfred in September, a paramount penalty for a front office member. To his “credit”, he got to keep Espinoza and Naylor.

Here we are over a year later and while the Marlins eventually dealt Castillo to the Reds for Dan Straily, the other pieces have stayed true.

Espinoza’s stock has come down from its peak level last year, but he still remains one of the minor league’s best righties. At the onset of this season, he was a consensus top 25 prospect, slotting in at number 21 with an A- grade ceiling from John Sickels.

Still just 19, he unfortunately lost 2017 to Tommy John surgery in what some vengeful minds call payback for Preller. While Preller deserves nothing but a swift kick in the (see: Red Forman), the dirty politics involved had absolutely nothing to do with Espinoza and we look forward to his return in 2018.

His results in 2016 weren’t great, but they were just fine. After lighting up the Dominican Summer League in his 2015 debut, he transitioned beautifully to rookie ball. The Venezuelan made only one appearance in Low-A, allowing three runs in three and a third innings.

For the year in its entirety, he struck out 65 batters in 58.1 innings.

That kind of strike out stuff at the lower levels almost guarantees a national spotlight, and Espinoza carried his momentum in that category into 2016. He continued to punch out batters (8.3 K/9 between Low-A Greenville with Boston and Low-A Fort Wayne with San Diego) but faced some growing pains with baserunners.

Unfortunately, we were unable to see him continue to grow this season. Fingers crossed for 2018.

Josh Naylor may have been a first round pick, but his 12th overall selection was befuddling for pretty much everybody outside the Miami organization. Perhaps the Marlins saw what everyone else saw soon after, because they gave up on him exceptionally quickly despite excellent early returns.

Barely a year since making him their top draft pick, they curiously used the Canadian first baseman to headline a package for free agent-to-be Andrew Cashner.

MLB: Miami Marlins at Washington Nationals Brad Mills-USA TODAY Sports

Miami was battling for a playoff spot and obviously could use the upgrade in the starting rotation, but to invest —and invest with one of their few cherished prospects— in Cashner was a stunner.

As noted, this was a contract year for a player unlikely to re-up in Miami and a player who had also spent a healthy amount of time on the disabled list. He also wasn’t pitching well, totaling a 4.76 ERA in 79.1 innings. At least it wasn’t just Cashner coming over, but Rea too.

Of course, the Padres didn’t disclose Rea’s full physical evaluation and he was traded back to San Diego, so the trade officially stands as Naylor-for-Cashner, with respect to former golden boy Jarred Cosart. (I also like perpetually injured reliever Carter Capps, but he’s...perpetually injured.)

Cashner, as promised, was a rental and is having a mighty fine season for the Texas Rangers. He’ll hit the open market once more this summer. His time in Miami was regrettable, to say the least. He somehow compiled a winning record (12-11) while putting up an ERA of 5.98 and a 1.474 WHIP.

His tenure in Miami will not go down in the same breath as Dontrelle Willis.

As for Naylor, he backtracked a little after a great debut performance in 2015, where he hit .327 but jacked only one homer. Like Chris Shaw with the Giants, he is a first base-only prospect who may eventually expand to an outfield corner by way of playing for a National League club. Shaw hit his way into San Francisco getting him at-bat’s in other spots and that’s certainly the goal for Naylor (and any prospect) as well.

Working in his favor, Naylor runs a bit, swiping 10 stolen bases in Low-A Greensboro last season before the trade. Still 20 years old, his speed may give way to more prototypical pop as he fills out. He also represented Canada on the World team in the 2016 Futures Game, going 2-for-3 with an RBI.

The Padres have been aggressive with the southpaw, advancing him from low to High-A upon acquiring his services. He was okay there initially but took off at the level in 2017, encouraged by the sneak peek he received the year before.

At High-A Lake Elsinore, he slashed .297/.361/.452 and had eight home runs with seven stolen bases. He’s intriguing, to say the very least. The club promoted him to Double-A San Antonio just two weeks after his 20th birthday and he’s destined to play the remainder of this season for the Missions with eyes on Triple-A El Paso sometime in 2018.

In 36 games for the Padres Double-A affiliate, he’s hitting .256 but has walked 15 times in 150 plate appearances. (Easy math for the win.) He has a pair of homers and stolen bases and in’s mid-season Top 30 prospects update, he is 10th in a talented Friars farm system.

A.J. Preller owes a lot to anti-inflammatories. But it may be some time before he nets someone’s top prospect in a trade. For now, he’s plenty happy with Espinoza and Naylor.