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After signing Nick Pivetta and Kyle Hart last week, San Diego Padres president of baseball operations A.J. Preller told reporters he intends to keep Dylan Cease as the leader and linchpin of the team’s starting rotation for 2025. He got extremely creative with the deals to which he signed Pivetta, Elias Díaz, and Michael King, using mutual options and heavy backloading to snap up talent at virtually no cost for this season. Meanwhile, he found an exceptionally inexpensive (if otherwise unexceptional) left field platoon, signing Jason Heyward and Connor Joe to bargain-basement deals.
Here’s the thing, though: creatively or not, signing those players has dragged the team’s projected 40-man payroll for 2025 up to about $207 million, and their competitive-balance tax payroll (which can’t be gamed by the backloading or the options that slosh money from quarter to quarter and year to year) to a whopping $263 million.
Trading Juan Soto last year allowed the Padres to stay below the CBT threshold for 2024, so they only lose one pick—their second-rounder—and $500,000 in spending power in next year’s international free-agent period. For a team that loves to collect and then trade high-end prospects, though, the thinness of the San Diego farm system is a huge problem. They’re set to pick 25th and 99th in July. That leaves them without the ability to infuse their system with new prospects this summer who might excite any potential trade partners, be it next winter or in summers and winters to come.
San Diego's window could be closing after this year, and Preller might prefer to maximize the viability of winning in 2025. That would be out of character for him, though, and after their terrific 2024 campaign, he shouldn't feel the same job insecurity that hangs over Chicago counterpart Jed Hoyer right now. Preller likes to acquire great players, and he likes to do it when they have multiple years of team control. By contrast, he doesn't mind trading away high-octane talents when they have just one year of control left.
Right now, he has three players set to hit free agency as (more or less) stars this fall: Cease, King, and Luis Arraez. If this season goes well, the Padres could hand all three qualifying offers, and they'd probably only have to worry about Arraez accepting it. In the 2026 Draft, they could begin to rebuild a farm system. That's too late, though. Few executives have shown as sharp an eye for the time value of prospects as Preller. He doesn't want draft picks and IFA spending power in exchange for all three of these guys. He might be happy to take it for two of them, since that seems to be how things are playing out, but his track record says he will trade Cease, for a premium package.
For Soto, last winter, he got King, catcher Kyle Higashioka, and three touted pitching prospects—one of whom he later flipped as part of the deal that got him Cease. He'll continue to convert elite talent into good players with more team control, to amass the game's most important form of capital: on-field talent at sub-market prices.
That brings us, at last, to the Cubs—the team this site is mostly about, and the one you probably expected to be reading about here. As has been true at various points throughout the second half of this offseason, Hoyer and Preller find themselves circling each other, dance partners so obvious that it becomes awkward, the dance floor too big and their eyes locked on too early, while the distance to cover is still intimidating.
All winter, the Cubs have been engaged in these types of staredowns. They didn't even get to hang around as long as they wanted to in the Roki Sasaki derby, but they were a close second with robust offers for both Tanner Scott and Alex Bregman. Those free-agent sweepstakes all unfolded slowly, and (in their own ways) so did the moves the team actually has pulled off, trading for Kyle Tucker and Ryan Pressly and (even as they hammered out the Tucker deal) sending away Cody Bellinger. It's been a whole offseason of Hoyer and his staff fighting for leverage, in negotiations that favored other parties (be it because of the limitations on Hoyer's budget, the desirability of other destinations, or thorny logistics). Every move has felt like a long stalking maneuver—and so, crucially and maddeningly, have the not-quite-moves.
Chicago and San Diego first touched base about the possibilities of various trades in November. They began sorting through options more seriously last month, but when the Padres got the Díaz and King deals done and the Cubs needed to shift focus to reeling in Pressly, the potential for a blockbuster trade faded into the background. It began to reemerge, with Cease at the center, two weeks ago, only to be pushed off the front burner again by the intensification of the Bregman courtship.
Now, though, there's nothing left to truly draw away the attention of Hoyer or Preller. Yes, the Cubs also need a bench piece to round out their roster, with or without Cease. Whoever they add will be relatively easily signed, though—the blessedly painless kind of minor move of which they've also made a few this year, without losing sight of the bigger prizes in play. Whatever ancillary role player the team adds now would be a small enough expenditure not to interfere with a pursuit of Cease, as signing Bregman would have done.
The Padres have other suitors for Cease. They could trade him to Baltimore, the Mets, or Minnesota, to name three much-discussed suitors of varying degrees of plausibility. Right now, the structures of the offers going each way—the caliber of the headline piece and the number of secondary pieces involved—are such that the Cubs and Padres can't be called close to anything. We've reached the point of the offseason wherein that could change very quickly, but again, this is one last staring contest. It's very much still in play; that doesn't mean it will happen. It certainly doesn't have to happen soon, or not at all, as became the case with the Bregman, Scott, Pressly and Tucker deals at previous stages of the hot stove.
I don't believe Cease will be a Padre on Opening Day. The money says he won't. Preller's history (including, but not by any means limited to, his trade for Cease last Mar. 13; the deal that sent Chris Paddack and Emilio Pagán to Minnesota for Taylor Rogers and Brent Rooker on the eve of Opening Day 2022; and the deal that brought him Craig Kimbrel and B.J. Upton on Apr. 5, 2015) says he won't. The Cubs aren't ready to pay anywhere near the price Preller wants for Cease, and he might get that price more easily elsewhere. Still, as the season draws nearer, it's perfectly possible that one side or the other will blink.
The two sides have remained in touch about it, and breaking off that contact now feels as unlikely as a trade does. Despite the Tucker deal and all those admirable moves to bolster his depth, Hoyer and the rest of the front office were crestfallen when they lost out on Sasaki, on Scott, and on Bregman. This is their last chance to put the finishing touch on the winter that they've sought for a solid month. They'll wait it out, at the very least. And the pressure on the other guy, for once, feels just as high as the pressure on them.
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