The most painful trade Astros could make at Winter Meetings despite payroll crunch

The Houston Astros could take numerous trade paths this offseason. In an ideal world, Houston could find a team or teams willing to take Christian Walker and/or Lance McCullers Jr. off their hands. It would free up some much needed payroll space and playing time for better players.

More realistically, however, it feels like there's enough demand to expect a Jake Meyers trade this offseason. But the Astros could go in a different direction at the Winter Meetings that would yield a massive return. It would, however, come at the painful cost.

After last year's Winter Meetings saw Houston ship Kyle Tucker to the Chicago Cubs, fans know all too well that the Astros are more than willing to pull the trigger on big trades. Those same fans also know that the Astros would prefer to keep Jeremy Peña around for the long haul, but hiring Scott Boras as his agent made any extension possibility a lot less likely.

If Houston really needed to free up some cash while also looking to land a significant prospect package in return, the answer to all of these problems could be staring them in the face. But would Houston really take that unfortunate step of trading Peña at the Winter Meetings?

If the Astros preferred trade options fall through, Houston could trade Jeremy Peña

Now, this sort of trade would be incredibly difficult to finalize and come with substantial risk for the Astros. Peña has three more years of team control remaining, and just put up arguably the best season of his career. The odds of Houston finding someone — internal or external — to replace Peña at shortstop (and be as good or an upgrade) are very, very slim.

That doesn't mean, however, that there is no way to make it work. A shortstop-needy team like the Atlanta Braves would move mountains to get ahold of player like Peña. If the Astros were willing to trade their infielder, they could probably get a chunk of Walker's money off their books (Atlanta could use a DH anyways) and still net a near-big league ready starting pitching prospect like JR Ritchie. The details after that would be up in the air, but you get the general idea.

With that being said, trading Peña at the Winter Meetings feels very unlikely. Even if the Astros wanted to get a deal done (and it feels like they may want to at least try to sign him to an extension), Houston still plans to compete in 2026. There's little doubt the Astros would be significantly worse without Peña on the roster. Moving Meyers or one of the Astros' crummy contract will be the initial plan for a while.

Now, if we get to mid-January and the Astros haven't been able to get anything done, don't be surprised if the possibility of trading Peña pops up again.