Missing the postseason for the second year in a row could lead to questions about Preller’s future in San Diego

There might not be an executive in baseball who is more aggressive and willing to make a big deal than Padres president of baseball operations A.J. Preller.

Preller did it again last week, adding to the long list of deals on his resume by acquiring two-time All-Star second baseman Luís Arraez from the Marlins for a package of prospects. Arraez, who has eight hits in his first five games with San Diego, is under club control until the end of the 2025 season.

“I’m super excited [about Luis],” Padres manager Mike Shildt said this week. “You’re talking about an elite talent with the bat in this league. And so you put him at the top of our lineup with some of the people behind him. It’s only going to lengthen our lineup and strengthen it.”

San Diego’s model for player acquisition has been pretty clear since Preller took over in 2014: Draft and sign players internationally, develop them in the minors and then flip those assets to improve the big-league roster. While every team in baseball is trying to identify and develop talent, the Padres’ unique combination of an elite farm system, an aggressive front office and an ownership group willing to spend has separated them from the rest of the league when it comes to player acquisition. Other teams might be willing to wait for prospects to develop into the players they’ll become; San Diego has instead chosen to acquire established players to get better.

Since 2019, the list of players San Diego has signed as free agents or traded for is vast. Manny Machado, Ha-Seong King, Xander Bogaerts, Jurickson Profar, Jake Cronenworth, Juan Soto, Josh Hader, Yu Darvish, Blake Snell, Mike Clevinger, Joe Musgrove, Robert Suarez, Dylan Cease and Arraez all came to the Padres via trade or free agency. Even Fernando Tatis Jr. was acquired from the White Sox in a 2016 trade for right-hander James Shields. In fact, 89.5% of the Padres roster was originally signed or drafted by another organization. Only Jackson Merrill, Adrian Morejon and Luis Campusano were developed by the Padres.

“A.J. is always going to be aggressive,” Shildt told Yahoo Sports. “The biggest thing is making sure that we continue to have a continuity of how we play and there’s a consistency of identity, how we compete and how we look to bring everybody together on a daily basis.”

Of course, the cost of acquiring as much talent as the Padres have over the past five years is that they’ve traded away a significant amount of prospect capital — and not just middle-of-the-road, lottery ticket prospects. San Diego has given up blue-chip prospects with the potential to help turn a franchise around, something many of them are now in the process of doing elsewhere. The list of players Preller has traded away since 2019 includes Josh Naylor, CJ Abrams, David Bednar, Gabriel Arias, Edward Olivares, Cal Quantrill, MacKenzie Gore and Francisco Mejia, as well as prospects James Wood, Robert Hassell III, Drew Thorpe, Jakob Marsee and last year’s first-round pick, Dillon Head.

Not all these trades have generated the effect San Diego wanted. After acquiring generational hitter Juan Soto from the Nationals for a massive haul in 2022, the Padres sent him to the Yankees just 16 months later.

Going forward, the trade for Arraez makes the Padres’ ability to make other moves at the deadline a bit limited. When a team such as the Marlins is willing to trade a two-time batting champ six weeks into the season and pay nearly all of his salary, it’s hard to turn that down, but while Arraez provides an undeniable boost to San Diego’s offense, the Padres, like most teams trying to contend, have other areas of need, starting pitching being the main one.

The team’s rotation has struggled to start the season and currently owns a 4.18 ERA, which has been helped significantly by the recent performances of Darvish and Cease. The Padres could use another arm, but in light of the massive haul of prospects they’ve unloaded recently, it’s fair to question if the organization has the prospect capital to make another splash at the deadline.

Which brings us to the real problem for the Padres: Despite their aggressiveness in trades and free agency over the past five seasons, the acquisitions have not been nearly as fruitful as the team would’ve liked. San Diego has reached the postseason just twice in that span, resulting in a first-round sweep by the Dodgers in 2020 and a six-game defeat to the Phillies in the 2022 NLCS.

Last season, San Diego’s roster was thought to be capable of another deep postseason run, but instead they fell flat and were unable to turn it on until the final stretch of the season. By that point, it was too late. The Padres missed the postseason by two games.

Now, after moving on from former manager Bob Melvin, hiring Shildt as his replacement and reshuffling the deck with the Soto trade, missing the postseason two years in a row isn’t an option. Between the investment in the team’s payroll over the next decade and the fact that the farm system has been depleted significantly in recent years, the pressure on this team to reach the postseason and make a deep run once there is at an all-time high.

Preller knows that, and his continued aggressiveness with the Arraez trade could be interpreted as trying to buy himself some time while he attempts to save his job. He has been San Diego’s top executive since 2014 and is the fourth-longest-tenured lead executive in baseball. But two playoff appearances in the 10 years since he took over leave a lot to be desired.

What’s more, late Padres owner and chairman Peter Seidler was Preller’s biggest advocate. With Seidler’s passing this offseason came a changing of the guard in the team’s ownership group, including Eric Kutsenda taking over as chairman and interim control person. There’s no telling what the team might do after this season. Missing the postseason two years in a row after a flurry of transactions and with significant money invested in the roster Preller built will only lead to more questions about whether he is the right person to lead San Diego into the future.

But if his 10 years at the forefront of the Padres’ front office have shown anything, it’s that Preller won’t be scared to make the big move, and he’ll likely keep swinging until he can’t anymore. If the mission fails, it won’t be because Preller and the Padres didn’t go for it.

By the end of this season, we’ll find out if their aggressiveness was worth it or if it will become a cautionary tale of what could have been.