3 trades AJ Preller and Padres wish they could undo as deadline approaches

Few MLB general managers have made as many moves that changed the course of their franchise's history as much as San Diego Padres boss AJ Preller. From key moves while the Padres were emerging from their doldrums, including for Fernando Tatis Jr. and Jake Cronenworth, to the high-profile dives as the team pushed their chips in for Blake Snell, Josh Hader and Juan Soto, Preller has been in the middle of almost every trade market since he took the job.

However, being one of the most consequential modern GMs does not mean he hasn't missed with some of his moves. This is the same man that willingly gave Eric Hosmer $144 million, after all. In fact, some of his trades have aged so poorly that they reverberate throughout the Padres' roster even now.

Here is a look at some of Preller's trades that the Padres wish they could take back with the benefit of hindsight.

Trading Trea Turner for Wil Myers

Going out and trading for Wil Myers was always a very dicey gamble, even back in 2014. Preller was just a few months into the job and wasted little time in trying to shape the Padres' roster in his image. Nevermind the fact that Myers was coming off a sophomore campaign where he hit .222 and missed a bunch of time with a stress fracture in his wrist. Preller wanted him and went out and got him.

Unfortunately, the price for Myers included the Padres giving up their 2014 first-round pick ... Trea Turner. Myers went on to play eight mediocre seasons in San Diego while Turner went on to be one of the best shortstops in baseball. In an ideal world, San Diego probably would have held on to Turner instead of throwing a ton of money at Xander Bogaerts, and would've been in a better position in the years since (as well as at this year's deadline).

Trading Max Fried for Justin Upton

San Diego clearly has some issues in their rotation right now. Yu Darvish's status is up in the air, Joe Musgrove is still working his way back from arm troubles, and we don't know if Adam Mazur will get past his initial struggles in the big leagues. However, in an alternate dimension, the Padres would have never traded away Max Fried for one season of Justin Upton.

To be clear, Upton wasn't "bad" with San Diego (although he also wasn't awesome). He hit 26 homers and made the All-Star team. However, he also skipped town in free agency to sign a six-year deal with the Tigers while Fried turned into one of the best left-handers in baseball and is under team control through the end of this season. Seems like an arm that would be really nice to have right about now.

Trading an absolute mountain of top prospects for Juan Soto

This is pure revisionism with the benefit of hindsight. At the time of the Juan Soto trade, the Padres were officially all-in and Soto was (and still is) one of the best players in all of baseball. San Diego had to pay a heavy price to land him, but that is the risk one has to take to get such a premier talent, and the team was lauded for being willing to make such an aggressive move at the time.

Unfortunately, the deal has not aged well. The Padres' 2023 season turned into flaming garbage and San Diego was "forced" to trade Soto away after getting just a season and a half out of him. Making matters worse, the package of prospects that the Padres gave up to acquire Soto is paying huge dividends for the Nationals. Just imagine what this San Diego would look like with CJ Abrams, James Wood, and Mackenzie Gore still around. Tough to think about, actually.

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