Most painful trade Padres could make at Winter Meetings to escape payroll crunch

If we’re being honest, the true answer to “most painful trade” is Fernando Tatis Jr. Or even Jackson Merrill. You don’t need a thinkpiece to know that would melt half of San Diego into the Pacific.

But we live on Planet Reality, and on that planet the most painful, actually plausible move the Padres could make at the Winter Meetings has a different name on it. Jake Cronenworth.

Padres’ most painful path out of a payroll crunch runs through Jake Cronenworth

Cronenworth is exactly the kind of player winning teams quietly build around and then only truly appreciate once he’s gone. He’s not the loudest star in the room, but he’s a left-handed, multi-position grinder who has done just about everything this organization has asked of him. First base, second base, short in a pinch, clutch at-bats in big moments — he’s been the duct tape holding a lot of weird roster fits together. And that’s exactly why this would hurt.

He’s also locked into a not-insane-but-not-nothing commitment: five years, $60 million left on the deal. He hasn’t really climbed back to the All-Star level we saw in 2021 and 2022, but he’s still grinding. A .246/.367/.377 line with 11 home runs, 59 RBIs, and a 2.4 WAR is the profile of a guy getting his hands dirty every night to help his team stack wins. 

For a big-market Padres team with full-on 2022 vibes, that’s just the cost of doing business. For the 2025–26 Padres trying to escape a payroll crunch while still patching holes, that same contract suddenly looks like a lever you might actually pull.

With Tatis, Machado, and Bogaerts wrapped in full no-trade armor and massive contracts, there just aren’t many movable pieces that both (a) save real money and (b) bring back anything resembling value. Cronenworth checks both boxes, which is exactly why this conversation exists at all.

Move him, and you open up real flexibility — maybe enough to add a mid-rotation starter and a credible bat. But you’re also detonating a big chunk of your infield stability and leadership, and betting you can replace his versatility and left-handed stick on the cheap.

Honorable mention in the “why does this feel so gross?” category: a weird, multi-team style deal that ships out Randy Vásquez. He’s a young, improving arm who finally looked like he was figuring it out, exactly the type of controllable starter you should be hoarding. Flipping him just to backfill with some mid-tier, more expensive pitching would be the kind of galaxy-brain maneuver that keeps Padres fans up at night.

The Padres might have to do something painful at the Winter Meetings to escape this payroll crunch. Let’s just hope “necessary” doesn’t turn into “regrettable” in real time.