3 regrets the Padres should already have about the 2023-24 offseason

There are more than a few reasons to be exasperated with the San Diego Padres at this point. Whether it's spending too much money and then not enough, giving controversially large contracts to players who will only be able to make good on half of their guaranteed years and then trading away young stars, and so — there are actually a lot of reasons to be exasperated with the Padres. This offseason has only made thing worse, as the Friars seemingly stay still and watch not only the rest of their division but the rest of the league pass them by.

There are less than two months now until pitchers and catchers report, and San Diego has almost nothing to show for their time off. Here are three regrets the Padres should have this offseason.

Not getting more from the Yankees in the Juan Soto trade

Trading Juan Soto away was in the works for months and, especially given how drawn-out the conclusion was, felt like an inevitability by the time it actually happened. Apart from the obvious, general sadness about losing a star, we probably won't know exactly how much the team should regret letting Soto go until we get a little ways into the 2024 season. However, we can take a look at what the Padres got in return, which was largely pitching help. Michael King will be a good addition to the rotation, Kyle Higashioka will be a fine backup catcher, and Jhony Brito and Randy Vásquez will be good for the bullpen.

However, the Padres should've considered dealing or pressed harder with the Yankees for a replacement outfielder for Soto. At the moment, San Diego's outfield selection is unbearably thin after also they packaged in Trent Grisham to the Yankees. It features only José Azocar and Fernando Tatis Jr., according to MLB.com's depth chart. Around the same time the Padres and Yankees were trying to sort the Soto deal out, the Yankees were also dealing with the Red Sox on a trade for Alex Verdugo. Speculation that Verdugo was going to be flipped to the Padres was quickly debunked, but maybe they should have pushed for Verdugo to be part of the deal. He would've been a better culture fit in San Diego and is a stronger defensive outfielder than Soto.

The Yankees also have a few young outfielders that the Padres could've asked for — Oswaldo Cabrera, Estevan Florial, and Everson Pereira among them with varying degrees of major league experience. If San Diego can find good outfielders on the trade or free agent markets in a year that's wanting for non-pitchers, then good on them, and this might not need to be a regret down the line. For now, though, with only two options for three available outfield spots, the Padres should be wishing they asked for a little more from the Yankees.

Not spending any money at all

It's true that letting players like Shohei Ohtani, Eduardo Rodriguez, Jung Hoo Lee, who received a larger contract than anyone expected, and Yoshinobu Yamamoto, whose contract is now expected to exceed $200 million, pass by in the interest of cutting down payroll, the Padres seem to also be ignoring good options that even smaller market teams are able to afford. They made a seemingly limp attempt at keeping Seth Lugo, but lost him because they weren't willing to spend Kansas City Royals (...?) kind of money. Michael Wacha followed just days later. Arms like Kenta Maeda and Jack Flaherty, perhaps a bit dangerous for various reasons but nevertheless experienced and affordable, have gone to the Tigers.

Teams that well below league average in 2023 are being consistently more aggressive on the free agent market, but importantly teams like the Royals are setting clear expectations about how much they can spend, and they're actually spending. Transparency isn't something that the Padres can't afford either, evidently, and while this hopefully means that something is quietly in the works, it also could just mean that there's little for us to expect this year.

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